CA2380981A1 - Fluorene derivatives - Google Patents
Fluorene derivatives Download PDFInfo
- Publication number
- CA2380981A1 CA2380981A1 CA002380981A CA2380981A CA2380981A1 CA 2380981 A1 CA2380981 A1 CA 2380981A1 CA 002380981 A CA002380981 A CA 002380981A CA 2380981 A CA2380981 A CA 2380981A CA 2380981 A1 CA2380981 A1 CA 2380981A1
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- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
- 239000012453 solvate Substances 0.000 claims abstract description 16
- 108010044426 integrins Proteins 0.000 claims abstract description 14
- 102000006495 integrins Human genes 0.000 claims abstract description 14
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 9
- 206010003210 Arteriosclerosis Diseases 0.000 claims abstract description 8
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 8
- 208000011775 arteriosclerosis disease Diseases 0.000 claims abstract description 8
- 208000035475 disorder Diseases 0.000 claims abstract description 8
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 7
- 239000003112 inhibitor Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 8
- 206010061216 Infarction Diseases 0.000 claims description 7
- 230000002491 angiogenic effect Effects 0.000 claims description 7
- 239000005557 antagonist Substances 0.000 claims description 7
- 230000000747 cardiac effect Effects 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 230000007574 infarction Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 208000029078 coronary artery disease Diseases 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
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- 101710149643 Integrin alpha-IIb Proteins 0.000 claims description 4
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- 150000002148 esters Chemical class 0.000 claims description 4
- 230000001575 pathological effect Effects 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 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 claims description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- PZXSTXXJKLWVBG-UHFFFAOYSA-N 2-(butylsulfonylamino)-3-[7-[2-(4,5-dihydro-1h-imidazol-2-ylamino)ethyl]-9h-fluoren-2-yl]propanoic acid Chemical compound C=1C(CC(NS(=O)(=O)CCCC)C(O)=O)=CC=C(C2=CC=3)C=1CC2=CC=3CCNC1=NCCN1 PZXSTXXJKLWVBG-UHFFFAOYSA-N 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 2
- 208000019622 heart disease Diseases 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- MBYMPMDJWZKQLM-UHFFFAOYSA-N 3-[7-[2-(4,5-dihydro-1h-imidazol-2-ylamino)ethyl]-9h-fluoren-2-yl]-2-(2,2-dimethylpropoxycarbonylamino)propanoic acid Chemical compound C=1C(CC(NC(=O)OCC(C)(C)C)C(O)=O)=CC=C(C2=CC=3)C=1CC2=CC=3CCNC1=NCCN1 MBYMPMDJWZKQLM-UHFFFAOYSA-N 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 4
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- 230000017531 blood circulation Effects 0.000 abstract 1
- 230000009054 pathological process Effects 0.000 abstract 1
- 230000000644 propagated effect Effects 0.000 abstract 1
- -1 benzyloxycarbonyl DCCI Chemical compound 0.000 description 133
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000007327 hydrogenolysis reaction Methods 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- 210000004881 tumor cell Anatomy 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 102000008946 Fibrinogen Human genes 0.000 description 5
- 108010049003 Fibrinogen Proteins 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 229940012952 fibrinogen Drugs 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 108010012088 Fibrinogen Receptors Proteins 0.000 description 4
- 210000001772 blood platelet Anatomy 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
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- 238000002347 injection Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000005167 vascular cell Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole 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 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
-
- 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
- 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
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/12—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19937394.9 | 1999-08-07 | ||
| DE19937394A DE19937394A1 (de) | 1999-08-07 | 1999-08-07 | Fluorenderivate |
| PCT/EP2000/007153 WO2001010841A2 (de) | 1999-08-07 | 2000-07-26 | Fluorenderivate als integrin inhibitoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2380981A1 true CA2380981A1 (en) | 2001-02-15 |
Family
ID=7917613
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002380981A Abandoned CA2380981A1 (en) | 1999-08-07 | 2000-07-26 | Fluorene derivatives |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1208088A2 (cs) |
| JP (1) | JP2003506439A (cs) |
| KR (1) | KR20020012631A (cs) |
| CN (1) | CN1368962A (cs) |
| AR (1) | AR025042A1 (cs) |
| AU (1) | AU6828600A (cs) |
| BR (1) | BR0013083A (cs) |
| CA (1) | CA2380981A1 (cs) |
| CZ (1) | CZ2002298A3 (cs) |
| DE (1) | DE19937394A1 (cs) |
| HK (1) | HK1049006A1 (cs) |
| HU (1) | HUP0202464A3 (cs) |
| MX (1) | MXPA02001297A (cs) |
| NO (1) | NO20020592L (cs) |
| PL (1) | PL353054A1 (cs) |
| SK (1) | SK1402002A3 (cs) |
| WO (1) | WO2001010841A2 (cs) |
| ZA (1) | ZA200201873B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101102808B1 (ko) * | 2010-04-13 | 2012-01-05 | 윤태삼 | 라이저 인장 장치 |
| US8574899B2 (en) | 2010-12-22 | 2013-11-05 | Vladimir B Serikov | Methods for augmentation collection of placental hematopoietic stem cells and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04506350A (ja) * | 1989-06-22 | 1992-11-05 | ノバ ファーマスーティカル コーポレイション | 炎症の処置用の医薬組成物及び炎症の処置方法 |
| IL113196A0 (en) * | 1994-03-31 | 1995-06-29 | Bristol Myers Squibb Co | Imidazole derivatives and pharmaceutical compositions containing the same |
| EP0889877B1 (en) * | 1996-03-29 | 2001-08-29 | G.D. Searle & Co. | META-SUBSTITUTED PHENYLENE DERIVATIVES AND THEIR USE AS ALPHAvBETA3 INTEGRIN ANTAGONISTS OR INHIBITORS |
| DE19654483A1 (de) * | 1996-06-28 | 1998-01-02 | Merck Patent Gmbh | Phenylalanin-Derivate |
| CA2214931A1 (en) * | 1996-09-26 | 1998-03-26 | Henry Uhlman Bryant | Tetrahydrobenzo-a-fluorene compounds and method of use |
-
1999
- 1999-08-07 DE DE19937394A patent/DE19937394A1/de not_active Withdrawn
-
2000
- 2000-07-26 EP EP00956284A patent/EP1208088A2/de not_active Withdrawn
- 2000-07-26 AU AU68286/00A patent/AU6828600A/en not_active Abandoned
- 2000-07-26 KR KR1020027000660A patent/KR20020012631A/ko not_active Withdrawn
- 2000-07-26 MX MXPA02001297A patent/MXPA02001297A/es not_active Application Discontinuation
- 2000-07-26 BR BR0013083-4A patent/BR0013083A/pt not_active Application Discontinuation
- 2000-07-26 CN CN00811476A patent/CN1368962A/zh active Pending
- 2000-07-26 SK SK140-2002A patent/SK1402002A3/sk unknown
- 2000-07-26 HU HU0202464A patent/HUP0202464A3/hu unknown
- 2000-07-26 PL PL00353054A patent/PL353054A1/xx unknown
- 2000-07-26 CA CA002380981A patent/CA2380981A1/en not_active Abandoned
- 2000-07-26 JP JP2001515308A patent/JP2003506439A/ja active Pending
- 2000-07-26 WO PCT/EP2000/007153 patent/WO2001010841A2/de not_active Ceased
- 2000-07-26 CZ CZ2002298A patent/CZ2002298A3/cs unknown
- 2000-07-26 HK HK03101305.5A patent/HK1049006A1/zh unknown
- 2000-08-04 AR ARP000104035A patent/AR025042A1/es unknown
-
2002
- 2002-02-06 NO NO20020592A patent/NO20020592L/no not_active Application Discontinuation
- 2002-03-06 ZA ZA200201873A patent/ZA200201873B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SK1402002A3 (en) | 2002-06-04 |
| EP1208088A2 (de) | 2002-05-29 |
| ZA200201873B (en) | 2003-08-27 |
| CZ2002298A3 (cs) | 2002-04-17 |
| JP2003506439A (ja) | 2003-02-18 |
| AR025042A1 (es) | 2002-11-06 |
| NO20020592D0 (no) | 2002-02-06 |
| BR0013083A (pt) | 2002-04-23 |
| PL353054A1 (en) | 2003-10-06 |
| AU6828600A (en) | 2001-03-05 |
| KR20020012631A (ko) | 2002-02-16 |
| CN1368962A (zh) | 2002-09-11 |
| WO2001010841A3 (de) | 2001-09-07 |
| HUP0202464A3 (en) | 2003-02-28 |
| MXPA02001297A (es) | 2004-07-16 |
| DE19937394A1 (de) | 2001-02-08 |
| WO2001010841A2 (de) | 2001-02-15 |
| HK1049006A1 (zh) | 2003-04-25 |
| HUP0202464A2 (hu) | 2002-12-28 |
| NO20020592L (no) | 2002-04-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |