CA2337305A1 - Diacylhydrazine derivatives - Google Patents
Diacylhydrazine derivatives Download PDFInfo
- Publication number
- CA2337305A1 CA2337305A1 CA002337305A CA2337305A CA2337305A1 CA 2337305 A1 CA2337305 A1 CA 2337305A1 CA 002337305 A CA002337305 A CA 002337305A CA 2337305 A CA2337305 A CA 2337305A CA 2337305 A1 CA2337305 A1 CA 2337305A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compounds
- acid
- compound
- salts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 125000005077 diacylhydrazine group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 108010044426 integrins Proteins 0.000 claims abstract description 11
- 102000006495 integrins Human genes 0.000 claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 7
- 201000010099 disease Diseases 0.000 claims abstract description 7
- 239000003112 inhibitor Substances 0.000 claims abstract description 6
- 238000011282 treatment Methods 0.000 claims abstract description 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims abstract description 5
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 5
- 208000011775 arteriosclerosis disease Diseases 0.000 claims abstract description 5
- 230000000747 cardiac effect Effects 0.000 claims abstract description 5
- 239000012453 solvate Substances 0.000 claims abstract description 5
- 206010061216 Infarction Diseases 0.000 claims abstract description 4
- 230000033115 angiogenesis Effects 0.000 claims abstract description 4
- 208000029078 coronary artery disease Diseases 0.000 claims abstract description 4
- 230000007574 infarction Effects 0.000 claims abstract description 4
- 208000037273 Pathologic Processes Diseases 0.000 claims abstract description 3
- 230000009054 pathological process Effects 0.000 claims abstract description 3
- 230000000644 propagated effect Effects 0.000 claims abstract description 3
- -1 CODA Chemical group 0.000 claims description 61
- 125000006239 protecting group Chemical group 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000001439 semicarbazido group Chemical group [H]N([H])C(=O)N([H])N([H])* 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
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- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
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- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910018828 PO3H2 Inorganic materials 0.000 claims 1
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 abstract description 3
- 238000011321 prophylaxis Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000003776 cleavage reaction Methods 0.000 description 13
- 230000007017 scission Effects 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
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- 238000004949 mass spectrometry Methods 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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- 239000007858 starting material Substances 0.000 description 6
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 102000008946 Fibrinogen Human genes 0.000 description 5
- 108010049003 Fibrinogen Proteins 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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- 238000007327 hydrogenolysis reaction Methods 0.000 description 5
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- 108010012088 Fibrinogen Receptors Proteins 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 210000001772 blood platelet Anatomy 0.000 description 4
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- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ULLSWWGYZWBPHK-UHFFFAOYSA-N 5-(9h-fluoren-9-ylmethoxycarbonylamino)pentanoic acid Chemical compound C1=CC=C2C(COC(=O)NCCCCC(=O)O)C3=CC=CC=C3C2=C1 ULLSWWGYZWBPHK-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007821 HATU Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
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- 239000002775 capsule Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- PMHRIPHAMZXZRN-QMMMGPOBSA-N (3s)-4-amino-3-[2-[[3-(diaminomethylideneamino)benzoyl]carbamoyl]hydrazinyl]-4-oxobutanoic acid Chemical compound NC(N)=NC1=CC=CC(C(=O)NC(=O)NN[C@@H](CC(O)=O)C(N)=O)=C1 PMHRIPHAMZXZRN-QMMMGPOBSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/13—Amines
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- 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
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- 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
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19831710A DE19831710A1 (de) | 1998-07-15 | 1998-07-15 | Diacylhydrazinderivate |
| DE19831710.7 | 1998-07-15 | ||
| PCT/EP1999/004673 WO2000003973A1 (de) | 1998-07-15 | 1999-07-06 | Diacylhydrazinderivate als integrin-inhibitoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2337305A1 true CA2337305A1 (en) | 2000-01-27 |
Family
ID=7874107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002337305A Abandoned CA2337305A1 (en) | 1998-07-15 | 1999-07-06 | Diacylhydrazine derivatives |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6326403B1 (enExample) |
| EP (1) | EP1097127B1 (enExample) |
| JP (1) | JP2002520382A (enExample) |
| KR (1) | KR20010079520A (enExample) |
| CN (1) | CN1309633A (enExample) |
| AR (1) | AR019777A1 (enExample) |
| AT (1) | ATE234276T1 (enExample) |
| AU (1) | AU753333B2 (enExample) |
| BR (1) | BR9912072A (enExample) |
| CA (1) | CA2337305A1 (enExample) |
| DE (2) | DE19831710A1 (enExample) |
| DK (1) | DK1097127T3 (enExample) |
| ES (1) | ES2194486T3 (enExample) |
| HU (1) | HUP0102602A3 (enExample) |
| ID (1) | ID27168A (enExample) |
| NO (1) | NO20010203L (enExample) |
| PL (1) | PL345398A1 (enExample) |
| PT (1) | PT1097127E (enExample) |
| SK (1) | SK412001A3 (enExample) |
| TW (1) | TW448145B (enExample) |
| WO (1) | WO2000003973A1 (enExample) |
| ZA (1) | ZA200101267B (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4817503B2 (ja) | 1999-06-01 | 2011-11-16 | バイオジェン・アイデック・エムエイ・インコーポレイテッド | Ｖｌａ−１に対するブロッキングモノクローナル抗体および炎症性障害の処置のためのその使用 |
| UY26664A1 (es) * | 2000-04-14 | 2001-11-30 | Abbott Lab | Hidrazidas y alcoxiamidas inhibidoras de la angiogénesis. |
| US20020002152A1 (en) | 2000-04-14 | 2002-01-03 | Craig Richard A. | Hydrazide and alkoxyamide angiogenesis inhibitors |
| DE10040105A1 (de) | 2000-08-17 | 2002-02-28 | Merck Patent Gmbh | Peptid- und Peptidmimetika-Derivate mit Integrin-Inhibitor-Eigenschaften |
| DE10040103A1 (de) | 2000-08-17 | 2002-02-28 | Merck Patent Gmbh | Peptid- und Peptidmimetika-Derivate mit Integrin-Inhibitor-Eigenschaften II |
| DZ3415A1 (fr) * | 2000-08-31 | 2002-03-07 | Chiron Corp | Guanidinobenzamides comme mc4-r agonistes. |
| PT1385823E (pt) | 2001-04-09 | 2007-01-31 | Novartis Vaccines & Diagnostic | Compostos de guanidino como agonistas do receptor de melanocortina-4 (r-mc4) |
| EE200300509A (et) | 2001-04-13 | 2004-08-16 | Biogen, Inc. | Antikehad VLA-1 vastu |
| DE60333937D1 (de) | 2002-05-23 | 2010-10-07 | Novartis Vaccines & Diagnostic | Substituierte quinazolinone verbindungen |
| US7226577B2 (en) | 2003-01-13 | 2007-06-05 | Bracco Imaging, S. P. A. | Gastrin releasing peptide compounds |
| US7304161B2 (en) | 2003-02-10 | 2007-12-04 | Intrexon Corporation | Diaclhydrazine ligands for modulating the expression of exogenous genes in mammalian systems via an ecdysone receptor complex |
| US7456315B2 (en) | 2003-02-28 | 2008-11-25 | Intrexon Corporation | Bioavailable diacylhydrazine ligands for modulating the expression of exogenous genes via an ecdysone receptor complex |
| JP2007501861A (ja) | 2003-05-23 | 2007-02-01 | カイロン コーポレイション | Ｍｃ４−ｒアゴニストとしてのグアニジノ置換キナゾリノン化合物 |
| DE10325049A1 (de) * | 2003-06-02 | 2004-12-23 | Merck Patent Gmbh | Peptid- und Peptidmimetika-Derivate mit Integrin-Inhibitor-Eigenschaften III |
| US7368453B2 (en) | 2003-11-19 | 2008-05-06 | Chiron Corporation | Quinazolinone compounds with reduced bioaccumulation |
| WO2005117954A2 (en) | 2004-06-04 | 2005-12-15 | The Scripps Research Institute | Compositions and methods for treatment of neovascular diseases |
| JP4745175B2 (ja) * | 2005-12-28 | 2011-08-10 | 本田技研工業株式会社 | 自動二輪車 |
| CN105381459A (zh) * | 2006-05-25 | 2016-03-09 | 比奥根Ma公司 | 治疗中风的方法 |
| ES2672513T3 (es) | 2007-05-29 | 2018-06-14 | Intrexon Corporation | Ligandos de diacilhidrazina quirales para modular la expresión genética exógena a través del complejo del receptor de ecdisona |
| US10316095B2 (en) | 2012-02-16 | 2019-06-11 | Santarus, Inc. | Antibody formulations |
| SG11201506875YA (en) | 2013-03-15 | 2015-09-29 | Intrexon Corp | Boron-containing diacylhydrazines |
| CA2950390C (en) | 2014-05-30 | 2020-09-22 | Pfizer Inc. | Carbonitrile derivatives as selective androgen receptor modulators |
| CN104027805B (zh) * | 2014-06-18 | 2017-02-15 | 北京大学 | 抑制整合素α5的物质在制备预防内皮细胞激活和/或动脉粥样硬化的产品中的新用途 |
| MX2017003403A (es) | 2014-09-17 | 2017-06-19 | Intrexon Corp | Compuestos de diacilhidrazina que contienen boro. |
| IL274300B2 (en) | 2017-11-01 | 2024-09-01 | Arrowhead Pharmaceuticals Inc | Alpha v beta 6 integrin ligands, compositions comprising same and uses thereof |
| KR20230167082A (ko) | 2021-04-08 | 2023-12-07 | 애로우헤드 파마슈티컬스 인코포레이티드 | 진행성 당화 최종 산물에 대한 수용체의 발현을 억제하기 위한 RNAi 작용제, 그의 조성물, 및 사용 방법 |
| WO2023275715A1 (en) | 2021-06-30 | 2023-01-05 | Pfizer Inc. | Metabolites of selective androgen receptor modulators |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5051405A (en) * | 1989-10-10 | 1991-09-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Anti-thrombotic peptides and pseudopeptides |
| JPH06505978A (ja) * | 1991-02-05 | 1994-07-07 | スミスクライン・ビーチャム・コーポレイション | 芳香族エステルまたはアミドを含有する抗凝集性ペプチド |
| US5530028A (en) * | 1992-11-23 | 1996-06-25 | Rohm And Haas Company | Insecticidal N'-substituted-N,N'-diacylhydrazines |
| JPH08505846A (ja) * | 1992-12-29 | 1996-06-25 | スミスクライン・ビーチャム・コーポレイション | 血小板凝集阻害用化合物 |
| ATE227567T1 (de) | 1994-05-27 | 2002-11-15 | Merck & Co Inc | Präparate zur hemmung der durch osteoklasten vermittelten knochenresorption |
| US5482962A (en) * | 1994-07-22 | 1996-01-09 | Rohm And Haas Company | Insecticidal N,N'-disubstituted-N-N'-diacylhydrazines |
| EP0880511A4 (en) * | 1996-01-16 | 1999-06-16 | Merck & Co Inc | Integrin receptor antagonists |
-
1998
- 1998-07-15 DE DE19831710A patent/DE19831710A1/de not_active Withdrawn
-
1999
- 1999-07-06 AT AT99934576T patent/ATE234276T1/de not_active IP Right Cessation
- 1999-07-06 DE DE59904547T patent/DE59904547D1/de not_active Expired - Fee Related
- 1999-07-06 CA CA002337305A patent/CA2337305A1/en not_active Abandoned
- 1999-07-06 CN CN99808610A patent/CN1309633A/zh active Pending
- 1999-07-06 BR BR9912072-0A patent/BR9912072A/pt not_active IP Right Cessation
- 1999-07-06 PT PT99934576T patent/PT1097127E/pt unknown
- 1999-07-06 KR KR1020017000359A patent/KR20010079520A/ko not_active Withdrawn
- 1999-07-06 HU HU0102602A patent/HUP0102602A3/hu unknown
- 1999-07-06 ID IDW20010206A patent/ID27168A/id unknown
- 1999-07-06 WO PCT/EP1999/004673 patent/WO2000003973A1/de not_active Ceased
- 1999-07-06 EP EP99934576A patent/EP1097127B1/de not_active Expired - Lifetime
- 1999-07-06 JP JP2000560082A patent/JP2002520382A/ja active Pending
- 1999-07-06 PL PL99345398A patent/PL345398A1/xx unknown
- 1999-07-06 US US09/743,605 patent/US6326403B1/en not_active Expired - Fee Related
- 1999-07-06 DK DK99934576T patent/DK1097127T3/da active
- 1999-07-06 ES ES99934576T patent/ES2194486T3/es not_active Expired - Lifetime
- 1999-07-06 AU AU50313/99A patent/AU753333B2/en not_active Ceased
- 1999-07-06 SK SK41-2001A patent/SK412001A3/sk unknown
- 1999-07-13 TW TW088111860A patent/TW448145B/zh active
- 1999-07-14 AR ARP990103436A patent/AR019777A1/es not_active Application Discontinuation
-
2001
- 2001-01-12 NO NO20010203A patent/NO20010203L/no not_active Application Discontinuation
- 2001-02-14 ZA ZA200101267A patent/ZA200101267B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20010203D0 (no) | 2001-01-12 |
| PT1097127E (pt) | 2003-07-31 |
| CN1309633A (zh) | 2001-08-22 |
| AU753333B2 (en) | 2002-10-17 |
| TW448145B (en) | 2001-08-01 |
| NO20010203L (no) | 2001-01-12 |
| JP2002520382A (ja) | 2002-07-09 |
| EP1097127A1 (de) | 2001-05-09 |
| ZA200101267B (en) | 2002-10-04 |
| ES2194486T3 (es) | 2003-11-16 |
| DE59904547D1 (de) | 2003-04-17 |
| BR9912072A (pt) | 2001-09-25 |
| DE19831710A1 (de) | 2000-01-20 |
| ATE234276T1 (de) | 2003-03-15 |
| US6326403B1 (en) | 2001-12-04 |
| KR20010079520A (ko) | 2001-08-22 |
| AR019777A1 (es) | 2002-03-13 |
| WO2000003973A1 (de) | 2000-01-27 |
| DK1097127T3 (da) | 2003-06-10 |
| HUP0102602A2 (hu) | 2002-01-28 |
| PL345398A1 (en) | 2001-12-17 |
| ID27168A (id) | 2001-03-08 |
| EP1097127B1 (de) | 2003-03-12 |
| HUP0102602A3 (en) | 2002-02-28 |
| SK412001A3 (en) | 2001-08-06 |
| AU5031399A (en) | 2000-02-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |