KR20010042614A - 비트로넥틴 길항제로서 복소환식 글리실 베타-알라닌 유도체 - Google Patents
비트로넥틴 길항제로서 복소환식 글리실 베타-알라닌 유도체 Download PDFInfo
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- KR20010042614A KR20010042614A KR1020007011291A KR20007011291A KR20010042614A KR 20010042614 A KR20010042614 A KR 20010042614A KR 1020007011291 A KR1020007011291 A KR 1020007011291A KR 20007011291 A KR20007011291 A KR 20007011291A KR 20010042614 A KR20010042614 A KR 20010042614A
- Authority
- KR
- South Korea
- Prior art keywords
- aryl
- alkyl
- product
- amino
- hydroxy
- 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.)
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- -1 Heterocyclic glycyl beta-alanine derivatives Chemical class 0.000 title claims description 121
- 239000005557 antagonist Substances 0.000 title description 9
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- 150000001875 compounds Chemical class 0.000 claims abstract description 218
- 238000000034 method Methods 0.000 claims abstract description 103
- 108010044426 integrins Proteins 0.000 claims abstract description 24
- 102000006495 integrins Human genes 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 230000001404 mediated effect Effects 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims description 109
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 57
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 55
- 125000003545 alkoxy group Chemical group 0.000 claims description 49
- 125000001188 haloalkyl group Chemical group 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 25
- 125000004414 alkyl thio group Chemical group 0.000 claims description 25
- 125000004104 aryloxy group Chemical group 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000003368 amide group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
- 229940124530 sulfonamide Drugs 0.000 claims description 17
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- 206010028980 Neoplasm Diseases 0.000 claims description 16
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 15
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- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004442 acylamino group Chemical group 0.000 claims description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 11
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
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- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 9
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- 125000001475 halogen functional group Chemical group 0.000 claims description 8
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- 125000002252 acyl group Chemical group 0.000 claims description 7
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- 125000004995 haloalkylthio group Chemical class 0.000 claims description 7
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- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 7
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- 125000005361 aryl sulfoxide group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 5
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
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- 229930194542 Keto Natural products 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
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- 125000000468 ketone group Chemical group 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- VQJYYAYBKBRRDJ-UHFFFAOYSA-N 1-(2,6-difluorophenyl)-1,3-dihydro-[1,3]thiazolo[3,4-a]benzimidazole 2-oxide Chemical compound FC1=CC=CC(F)=C1C1S(=O)CC2=NC3=CC=CC=C3N12 VQJYYAYBKBRRDJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 208000002780 macular degeneration Diseases 0.000 claims description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical group O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 3
- 150000003007 phosphonic acid derivatives Chemical group 0.000 claims description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 2
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 2
- 150000003431 steroids Chemical class 0.000 claims description 2
- 235000000346 sugar Nutrition 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 159
- 238000005160 1H NMR spectroscopy Methods 0.000 description 133
- 239000000203 mixture Substances 0.000 description 124
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 119
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- 238000006243 chemical reaction Methods 0.000 description 110
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 108
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- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 93
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- 238000002360 preparation method Methods 0.000 description 80
- 235000019439 ethyl acetate Nutrition 0.000 description 78
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
- 238000005481 NMR spectroscopy Methods 0.000 description 66
- 230000002829 reductive effect Effects 0.000 description 64
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- 238000004007 reversed phase HPLC Methods 0.000 description 47
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 36
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- 238000003756 stirring Methods 0.000 description 34
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- 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
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- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- 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
- C07D417/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
-
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Heart & Thoracic Surgery (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Communicable Diseases (AREA)
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- Ophthalmology & Optometry (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8139498P | 1998-04-10 | 1998-04-10 | |
| US60/081,394 | 1998-04-10 | ||
| PCT/US1999/004297 WO1999052896A1 (en) | 1998-04-10 | 1999-04-09 | Heterocyclic glycyl beta-alanine derivatives as vitronectin antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20010042614A true KR20010042614A (ko) | 2001-05-25 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020007011291A Ceased KR20010042614A (ko) | 1998-04-10 | 1999-04-09 | 비트로넥틴 길항제로서 복소환식 글리실 베타-알라닌 유도체 |
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| Country | Link |
|---|---|
| EP (1) | EP1070060A1 (cs) |
| JP (1) | JP2002511462A (cs) |
| KR (1) | KR20010042614A (cs) |
| CN (1) | CN1304406A (cs) |
| AR (1) | AR015759A1 (cs) |
| AU (1) | AU765294B2 (cs) |
| BR (1) | BR9910119A (cs) |
| CA (1) | CA2326665A1 (cs) |
| CZ (1) | CZ20003672A3 (cs) |
| IL (1) | IL138677A0 (cs) |
| MY (1) | MY133473A (cs) |
| NO (1) | NO20005084L (cs) |
| NZ (1) | NZ507292A (cs) |
| PL (1) | PL343406A1 (cs) |
| RU (1) | RU2215746C2 (cs) |
| TW (1) | TWI247008B (cs) |
| WO (1) | WO1999052896A1 (cs) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US6172256B1 (en) * | 1998-03-04 | 2001-01-09 | G.D. Searle & Co. | Chiral-β-amino acid compounds and derivatives thereof |
| GB9805655D0 (en) | 1998-03-16 | 1998-05-13 | Celltech Therapeutics Ltd | Chemical compounds |
| US6521626B1 (en) | 1998-03-24 | 2003-02-18 | Celltech R&D Limited | Thiocarboxamide derivatives |
| GB9814414D0 (en) | 1998-07-03 | 1998-09-02 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9821061D0 (en) | 1998-09-28 | 1998-11-18 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9826174D0 (en) | 1998-11-30 | 1999-01-20 | Celltech Therapeutics Ltd | Chemical compounds |
| EP1140183A1 (en) * | 1998-12-23 | 2001-10-10 | G.D. Searle & Co. | Use of a matrix metalloproteinase inhibitor and an integrin antagonist in the treatment of neoplasia |
| JP2002536411A (ja) | 1999-02-09 | 2002-10-29 | ブリストル−マイヤーズ スクイブ カンパニー | Xa因子のラクタム系阻害剤および方法 |
| KR20010110750A (ko) | 1999-04-12 | 2001-12-13 | 앤드류 앵뉴 | 인테그린 길항제로서의 치환된 비사이클릭 헤테로아릴화합물 |
| GB9908355D0 (en) * | 1999-04-12 | 1999-06-09 | Rhone Poulenc Rorer Ltd | Chemical compounds |
| JP2003500339A (ja) * | 1999-04-28 | 2003-01-07 | ビーエーエスエフ アクチェンゲゼルシャフト | インテグリン受容体アンタゴニスト |
| US6518283B1 (en) | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
| US6455539B2 (en) | 1999-12-23 | 2002-09-24 | Celltech R&D Limited | Squaric acid derivates |
| ATE375330T1 (de) | 2000-04-17 | 2007-10-15 | Ucb Pharma Sa | Enamin-derivate als zell-adhäsionsmoleküle |
| US6545013B2 (en) | 2000-05-30 | 2003-04-08 | Celltech R&D Limited | 2,7-naphthyridine derivatives |
| US6403608B1 (en) | 2000-05-30 | 2002-06-11 | Celltech R&D, Ltd. | 3-Substituted isoquinolin-1-yl derivatives |
| WO2001096310A1 (en) * | 2000-06-15 | 2001-12-20 | Pharmacia Corporation | Dihydrostilbene alkanoic acid derivatives useful as vitronectin antagonists |
| WO2002010136A1 (en) | 2000-08-02 | 2002-02-07 | Celltech R & D Limited | 3-substituted isoquinolin-1-yl derivatives |
| US6511973B2 (en) | 2000-08-02 | 2003-01-28 | Bristol-Myers Squibb Co. | Lactam inhibitors of FXa and method |
| DE10204789A1 (de) * | 2002-02-06 | 2003-08-14 | Merck Patent Gmbh | Inhibitoren des Integrins alpha¶v¶beta6 |
| TW200307671A (en) | 2002-05-24 | 2003-12-16 | Elan Pharm Inc | Heteroaryl compounds which inhibit leukocyte adhesion mediated by α 4 integrins |
| BR0317487A (pt) * | 2002-12-20 | 2005-11-29 | Pharmacia Corp | O r-isÈmero de compostos de aminoácido beta como derivados de antagonistas de receptores de integrina |
| UA87854C2 (en) | 2004-06-07 | 2009-08-25 | Мерк Энд Ко., Инк. | N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators |
| EP2065381A1 (de) | 2007-10-18 | 2009-06-03 | Boehringer Ingelheim Pharma GmbH & Co. KG | CGRP Antagonisten |
| JP5366960B2 (ja) | 2007-10-18 | 2013-12-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Cgrpアンタゴニスト |
| JP2011504481A (ja) * | 2007-11-22 | 2011-02-10 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 有機化合物 |
| EP2251338A3 (de) | 2007-11-22 | 2011-06-08 | Boehringer Ingelheim International GmbH | Organische Verbindungen |
| CA2878469A1 (en) | 2012-07-18 | 2014-01-23 | Saint Louis University | Beta amino acid derivatives as integrin antagonists |
| US8716226B2 (en) | 2012-07-18 | 2014-05-06 | Saint Louis University | 3,5 phenyl-substituted beta amino acid derivatives as integrin antagonists |
| BR112016027778A2 (pt) | 2014-05-30 | 2017-08-15 | Pfizer | Usos de derivados de carbonitrila, sua combinação e sua composição farmacêutica |
| BR112018012981A2 (pt) | 2015-12-30 | 2018-12-04 | Saint Louis University | derivados do ácido meta-azacíclico amino benzoico como antagonistas de pan integrina com melhores propriedades farmacocinéticas |
| CA3042693A1 (en) * | 2016-11-08 | 2018-05-17 | Bristol-Myers Squibb Company | Pyrrole amides as .alpha.v integrin inhibitors |
| US20230192661A1 (en) * | 2020-05-14 | 2023-06-22 | Ube Corporation | 1, 4, 5, 6-tetrahydropyrimidine-2-amine derivative |
| WO2023275715A1 (en) | 2021-06-30 | 2023-01-05 | Pfizer Inc. | Metabolites of selective androgen receptor modulators |
| EP4431098A4 (en) * | 2021-11-12 | 2025-10-08 | Ube Corp | PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OR PREVENTION OF ALPORT SYNDROME |
| CN115626912B (zh) * | 2022-09-27 | 2024-03-26 | 中山大学 | 一种硫脲化合物及其制备方法与应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5120859A (en) * | 1989-09-22 | 1992-06-09 | Genentech, Inc. | Chimeric amino acid analogues |
| FR2676054B1 (fr) * | 1991-05-03 | 1993-09-03 | Sanofi Elf | Nouveaux composes n-alkylenepiperidino et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| RU2126001C1 (ru) * | 1995-01-10 | 1999-02-10 | Самдзин Фармасьютикал Ко., Лтд | Производные пиперазина и фармацевтическая композиция на их основе |
| CA2230209A1 (en) * | 1995-08-30 | 1997-03-06 | G.D. Searle & Co. | Meta-guanidine, urea, thiourea or azacyclic amino benzoic acid derivatives as integrin antagonists |
| DE19629816A1 (de) * | 1996-07-24 | 1998-01-29 | Hoechst Ag | Neue Cycloalkyl-Derivate als Inhibitoren der Knochenresorption und Vitronectinrezeptor-Antagonisten |
| CA2263999A1 (en) * | 1996-08-29 | 1998-03-05 | Merck & Co., Inc. | Integrin antagonists |
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- 1999-04-09 NZ NZ507292A patent/NZ507292A/en unknown
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- 1999-04-09 AR ARP990101636A patent/AR015759A1/es unknown
- 1999-04-09 RU RU2000128033/04A patent/RU2215746C2/ru not_active IP Right Cessation
- 1999-04-09 WO PCT/US1999/004297 patent/WO1999052896A1/en not_active Application Discontinuation
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- 1999-04-09 CA CA002326665A patent/CA2326665A1/en not_active Abandoned
- 1999-04-09 IL IL13867799A patent/IL138677A0/xx unknown
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- 1999-04-09 BR BR9910119-0A patent/BR9910119A/pt not_active IP Right Cessation
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2000
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| IL138677A0 (en) | 2001-10-31 |
| AU765294B2 (en) | 2003-09-11 |
| MY133473A (en) | 2007-11-30 |
| CA2326665A1 (en) | 1999-10-21 |
| PL343406A1 (en) | 2001-08-13 |
| JP2002511462A (ja) | 2002-04-16 |
| AR015759A1 (es) | 2001-05-16 |
| AU3449999A (en) | 1999-11-01 |
| WO1999052896A1 (en) | 1999-10-21 |
| RU2215746C2 (ru) | 2003-11-10 |
| CN1304406A (zh) | 2001-07-18 |
| EP1070060A1 (en) | 2001-01-24 |
| NZ507292A (en) | 2003-12-19 |
| CZ20003672A3 (cs) | 2001-08-15 |
| NO20005084D0 (no) | 2000-10-09 |
| NO20005084L (no) | 2000-11-27 |
| BR9910119A (pt) | 2001-10-09 |
| TWI247008B (en) | 2006-01-11 |
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