MXPA01008072A - Nuevos derivados de guanidina como inhibidores de la adhesion celular. - Google Patents
Nuevos derivados de guanidina como inhibidores de la adhesion celular.Info
- Publication number
- MXPA01008072A MXPA01008072A MXPA01008072A MXPA01008072A MXPA01008072A MX PA01008072 A MXPA01008072 A MX PA01008072A MX PA01008072 A MXPA01008072 A MX PA01008072A MX PA01008072 A MXPA01008072 A MX PA01008072A MX PA01008072 A MXPA01008072 A MX PA01008072A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- residue
- aryl
- formula
- cycloalkyl
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims abstract description 19
- 230000021164 cell adhesion Effects 0.000 title abstract description 5
- 150000002357 guanidines Chemical class 0.000 title description 7
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 35
- 102100022337 Integrin alpha-V Human genes 0.000 claims abstract description 31
- 108010048673 Vitronectin Receptors Proteins 0.000 claims abstract description 28
- 238000011321 prophylaxis Methods 0.000 claims abstract description 22
- 208000006386 Bone Resorption Diseases 0.000 claims abstract description 20
- 230000024279 bone resorption Effects 0.000 claims abstract description 20
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 19
- 230000008569 process Effects 0.000 claims abstract description 18
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 12
- 239000002464 receptor antagonist Substances 0.000 claims abstract description 3
- 229940044551 receptor antagonist Drugs 0.000 claims abstract description 3
- -1 hydroxy, amino Chemical group 0.000 claims description 107
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 206010027476 Metastases Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000009401 metastasis Effects 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- 230000004614 tumor growth Effects 0.000 claims description 4
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 3
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 206010038923 Retinopathy Diseases 0.000 claims description 3
- 125000000539 amino acid group Chemical group 0.000 claims description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 2
- 208000017169 kidney disease Diseases 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000000651 prodrug Substances 0.000 abstract description 42
- 229940002612 prodrug Drugs 0.000 abstract description 42
- 210000002997 osteoclast Anatomy 0.000 abstract description 20
- 239000004480 active ingredient Substances 0.000 abstract description 12
- 201000010099 disease Diseases 0.000 abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 239000002253 acid Substances 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 25
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- 238000012360 testing method Methods 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 150000001413 amino acids Chemical class 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000005557 antagonist Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 210000000988 bone and bone Anatomy 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 125000002837 carbocyclic group Chemical group 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 150000004702 methyl esters Chemical class 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000007821 HATU Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 6
- 125000002619 bicyclic group Chemical group 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- 208000020084 Bone disease Diseases 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- IYMAXBFPHPZYIK-BQBZGAKWSA-N Arg-Gly-Asp Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O IYMAXBFPHPZYIK-BQBZGAKWSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 238000002965 ELISA Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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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
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/16—Nitrogen atoms not forming part of a nitro radical acylated on said nitrogen atoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99102916A EP1028114A1 (en) | 1999-02-13 | 1999-02-13 | Novel guanidine derivatives as inhibitors of cell adhesion |
| PCT/EP2000/000895 WO2000047564A1 (en) | 1999-02-13 | 2000-02-04 | Novel guanidine derivatives as inhibitors of cell adhesion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA01008072A true MXPA01008072A (es) | 2002-07-30 |
Family
ID=8237555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA01008072A MXPA01008072A (es) | 1999-02-13 | 2000-02-04 | Nuevos derivados de guanidina como inhibidores de la adhesion celular. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6340679B1 (https=) |
| EP (2) | EP1028114A1 (https=) |
| JP (1) | JP4642242B2 (https=) |
| AT (1) | ATE273285T1 (https=) |
| AU (1) | AU768206B2 (https=) |
| CA (1) | CA2371789C (https=) |
| DE (1) | DE60012890T2 (https=) |
| ES (1) | ES2225086T3 (https=) |
| IL (1) | IL144725A0 (https=) |
| MX (1) | MXPA01008072A (https=) |
| WO (1) | WO2000047564A1 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19629816A1 (de) * | 1996-07-24 | 1998-01-29 | Hoechst Ag | Neue Cycloalkyl-Derivate als Inhibitoren der Knochenresorption und Vitronectinrezeptor-Antagonisten |
| US6972296B2 (en) | 1999-05-07 | 2005-12-06 | Encysive Pharmaceuticals Inc. | Carboxylic acid derivatives that inhibit the binding of integrins to their receptors |
| GEP20053477B (en) | 1999-08-13 | 2005-03-25 | Biogen Inc | Cell Adhesion Inhibitors and Pharmaceutical Compositions Containing Them |
| EP1443963B1 (en) | 2001-10-22 | 2014-05-21 | The Scripps Research Institute | Antibody targeting compounds |
| AU2004287875B2 (en) * | 2003-11-05 | 2011-06-02 | Bausch + Lomb Ireland Limited | Modulators of cellular adhesion |
| US7196112B2 (en) | 2004-07-16 | 2007-03-27 | Biogen Idec Ma Inc. | Cell adhesion inhibitors |
| DK2444079T3 (en) | 2005-05-17 | 2017-01-30 | Sarcode Bioscience Inc | Compositions and Methods for the Treatment of Eye Diseases |
| WO2007048127A2 (en) * | 2005-10-20 | 2007-04-26 | The Scripps Research Institute | Fc labeling for immunostaining and immunotargeting |
| ES2630406T3 (es) * | 2007-10-19 | 2017-08-21 | Sarcode Bioscience Inc. | Composición y procedimientos para el tratamiento de la retinopatía diabética |
| US8080562B2 (en) | 2008-04-15 | 2011-12-20 | Sarcode Bioscience Inc. | Crystalline pharmaceutical and methods of preparation and use thereof |
| EP2276508A4 (en) * | 2008-04-15 | 2011-12-28 | Sarcode Bioscience Inc | ADMINISTRATION OF LFA-1 ANTAGONISTS TO THE GASTROINTESTINAL SYSTEM |
| WO2009128934A1 (en) * | 2008-04-15 | 2009-10-22 | Sarcode Corporation | Topical lfa-1 antagonists for use in localized treatment of immune related disorders |
| EP2265124A4 (en) * | 2008-04-15 | 2011-12-28 | Sarcode Bioscience Inc | AEROSOLISED LFA-1 ANTAGONISTS FOR THE USE IN THE LOCAL TREATMENT OF IMMUNE DISEASES |
| EP2395992A2 (en) | 2009-02-10 | 2011-12-21 | The Scripps Research Institute | Chemically programmed vaccination |
| US8378105B2 (en) * | 2009-10-21 | 2013-02-19 | Sarcode Bioscience Inc. | Crystalline pharmaceutical and methods of preparation and use thereof |
| CA2879982C (en) | 2012-07-25 | 2020-09-01 | Sarcode Bioscience Inc. | Lfa-1 inhibitor and polymorph thereof |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5204350A (en) | 1991-08-09 | 1993-04-20 | Merck & Co., Inc. | Method of inhibiting osteoclast-mediated bone resorption by administration of n-heterocyclicalkyl-substituted phenyl derivatives |
| US5217994A (en) | 1991-08-09 | 1993-06-08 | Merck & Co., Inc. | Method of inhibiting osteoclast-mediated bone resorption by administration of aminoalkyl-substituted phenyl derivatives |
| US5250679A (en) | 1991-10-18 | 1993-10-05 | Genentech, Inc. | Nonpeptidyl platelet aggregation inhibitors having specificity for the GPIIb III.sub. receptor |
| AU674553B2 (en) | 1992-10-14 | 1997-01-02 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| JPH08504194A (ja) | 1992-12-01 | 1996-05-07 | メルク エンド カンパニー インコーポレーテッド | フィブリノーゲンレセプターアンタゴニスト |
| JPH10501222A (ja) | 1994-05-27 | 1998-02-03 | メルク エンド カンパニー インコーポレーテッド | 破骨細胞仲介骨吸収を抑制するための化合物 |
| EP0767792A4 (en) | 1994-06-29 | 2002-11-20 | Smithkline Beecham Corp | VITRONECTIN RECEPTOR ANTAGONISTS |
| EP0762882A4 (en) | 1994-06-29 | 2002-09-11 | Smithkline Beecham Corp | Vibronectin Receptor Antagonists |
| HUP9802675A3 (en) | 1995-08-14 | 2000-09-28 | Scripps Research Inst | Methods and compositions useful for inhibition of alfa-v beta-5 mediated angiogenesis |
| DE19548709A1 (de) * | 1995-12-23 | 1997-07-03 | Merck Patent Gmbh | Tyrosinderivate |
| KR20000022190A (ko) * | 1996-06-28 | 2000-04-25 | 플레믹 크리스티안 | 인테그린 저해제로서의 페닐알라닌 유도체 |
| DE19629816A1 (de) * | 1996-07-24 | 1998-01-29 | Hoechst Ag | Neue Cycloalkyl-Derivate als Inhibitoren der Knochenresorption und Vitronectinrezeptor-Antagonisten |
| EP0933367A1 (en) | 1997-12-19 | 1999-08-04 | Hoechst Marion Roussel Deutschland GmbH | Novel acylguanidine derivates as inhibitors of bone resorption and as vitronectin receptor antagonists |
| IL137423A0 (en) | 1998-01-23 | 2001-07-24 | Aventis Pharma Gmbh | Novel sulfonamide derivatives as inhibitors of bone resorption and as inhibitors of cell adhesion |
-
1999
- 1999-02-13 EP EP99102916A patent/EP1028114A1/en not_active Withdrawn
-
2000
- 2000-02-04 AU AU26699/00A patent/AU768206B2/en not_active Ceased
- 2000-02-04 MX MXPA01008072A patent/MXPA01008072A/es not_active IP Right Cessation
- 2000-02-04 CA CA002371789A patent/CA2371789C/en not_active Expired - Lifetime
- 2000-02-04 DE DE60012890T patent/DE60012890T2/de not_active Expired - Lifetime
- 2000-02-04 AT AT00905022T patent/ATE273285T1/de not_active IP Right Cessation
- 2000-02-04 ES ES00905022T patent/ES2225086T3/es not_active Expired - Lifetime
- 2000-02-04 IL IL14472500A patent/IL144725A0/xx unknown
- 2000-02-04 JP JP2000598485A patent/JP4642242B2/ja not_active Expired - Lifetime
- 2000-02-04 WO PCT/EP2000/000895 patent/WO2000047564A1/en not_active Ceased
- 2000-02-04 EP EP00905022A patent/EP1155003B1/en not_active Expired - Lifetime
- 2000-02-11 US US09/502,577 patent/US6340679B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2225086T3 (es) | 2005-03-16 |
| IL144725A0 (en) | 2002-06-30 |
| AU768206B2 (en) | 2003-12-04 |
| US6340679B1 (en) | 2002-01-22 |
| CA2371789C (en) | 2009-04-14 |
| EP1155003B1 (en) | 2004-08-11 |
| AU2669900A (en) | 2000-08-29 |
| EP1028114A1 (en) | 2000-08-16 |
| DE60012890D1 (de) | 2004-09-16 |
| DE60012890T2 (de) | 2005-08-25 |
| CA2371789A1 (en) | 2000-08-17 |
| WO2000047564A1 (en) | 2000-08-17 |
| ATE273285T1 (de) | 2004-08-15 |
| JP2002536438A (ja) | 2002-10-29 |
| JP4642242B2 (ja) | 2011-03-02 |
| EP1155003A1 (en) | 2001-11-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration | ||
| MM | Annulment or lapse due to non-payment of fees |