SK14372001A3 - Substituované bicyklické heteroarylové zlúčeniny ako antagonisty integrínu a farmaceutický prostriedok, ktorý ich obsahuje - Google Patents
Substituované bicyklické heteroarylové zlúčeniny ako antagonisty integrínu a farmaceutický prostriedok, ktorý ich obsahuje Download PDFInfo
- Publication number
- SK14372001A3 SK14372001A3 SK1437-2001A SK14372001A SK14372001A3 SK 14372001 A3 SK14372001 A3 SK 14372001A3 SK 14372001 A SK14372001 A SK 14372001A SK 14372001 A3 SK14372001 A3 SK 14372001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- alkyl
- optionally substituted
- aryl
- compounds
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 108010044426 integrins Proteins 0.000 title description 16
- 102000006495 integrins Human genes 0.000 title description 16
- 239000005557 antagonist Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 256
- -1 heteroaryldiyl Chemical group 0.000 claims abstract description 171
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 115
- 150000003839 salts Chemical class 0.000 claims abstract description 55
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 54
- 239000002253 acid Chemical group 0.000 claims abstract description 51
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 33
- 239000000651 prodrug Substances 0.000 claims abstract description 30
- 229940002612 prodrug Drugs 0.000 claims abstract description 30
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 29
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 25
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 23
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
- 239000012453 solvate Substances 0.000 claims abstract description 17
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 12
- 125000000732 arylene group Chemical group 0.000 claims abstract description 11
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
- 125000004419 alkynylene group Chemical group 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims abstract description 10
- 150000004677 hydrates Chemical class 0.000 claims abstract description 10
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 7
- 125000005724 cycloalkenylene group Chemical group 0.000 claims abstract description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 27
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 20
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 125000000524 functional group Chemical group 0.000 claims description 13
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 230000021164 cell adhesion Effects 0.000 claims description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 11
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 239000011593 sulfur Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 8
- 239000000543 intermediate Substances 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 6
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- 230000001668 ameliorated effect Effects 0.000 claims description 4
- 229910052786 argon Inorganic materials 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 4
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000005239 aroylamino group Chemical group 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 239000001273 butane Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- KPHMACREDSGBEK-UHFFFAOYSA-N 3-[5-[[2-[2-(2-methylanilino)-1,3-benzoxazol-6-yl]acetyl]amino]pyridin-2-yl]butanoic acid Chemical compound C1=NC(C(CC(O)=O)C)=CC=C1NC(=O)CC1=CC=C(N=C(NC=2C(=CC=CC=2)C)O2)C2=C1 KPHMACREDSGBEK-UHFFFAOYSA-N 0.000 claims description 2
- QEBMPSSBGWOGFB-UHFFFAOYSA-N 3-[5-[[2-[4-methyl-2-(2-methylanilino)-1,3-benzoxazol-6-yl]acetyl]amino]pyridin-2-yl]butanoic acid Chemical compound C1=NC(C(CC(O)=O)C)=CC=C1NC(=O)CC1=CC(C)=C(N=C(NC=2C(=CC=CC=2)C)O2)C2=C1 QEBMPSSBGWOGFB-UHFFFAOYSA-N 0.000 claims description 2
- HTFKAMFYXWBFIM-UHFFFAOYSA-N 3-[6-[[2-[2-(2-methoxyanilino)-1,3-benzoxazol-6-yl]acetyl]amino]pyridin-3-yl]butanoic acid Chemical compound COC1=CC=CC=C1NC(OC1=C2)=NC1=CC=C2CC(=O)NC1=CC=C(C(C)CC(O)=O)C=N1 HTFKAMFYXWBFIM-UHFFFAOYSA-N 0.000 claims description 2
- OYHMQPKSWPLBLQ-UHFFFAOYSA-N 3-[6-[[2-[2-(2-methylanilino)-1,3-benzoxazol-6-yl]acetyl]amino]pyridin-3-yl]butanoic acid Chemical compound N1=CC(C(CC(O)=O)C)=CC=C1NC(=O)CC1=CC=C(N=C(NC=2C(=CC=CC=2)C)O2)C2=C1 OYHMQPKSWPLBLQ-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- CLPSFMAETRLPJT-UHFFFAOYSA-N 3-[5-[[2-[2-(2-methoxyanilino)-1,3-benzoxazol-6-yl]acetyl]amino]pyridin-2-yl]butanoic acid Chemical compound COC1=CC=CC=C1NC(OC1=C2)=NC1=CC=C2CC(=O)NC1=CC=C(C(C)CC(O)=O)N=C1 CLPSFMAETRLPJT-UHFFFAOYSA-N 0.000 claims 1
- 235000007119 Ananas comosus Nutrition 0.000 claims 1
- 244000099147 Ananas comosus Species 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 150000001555 benzenes Chemical group 0.000 claims 1
- SQIIOMYKKDNKJQ-UHFFFAOYSA-N butanoic acid;2,2,2-trifluoroacetic acid Chemical compound CCCC(O)=O.OC(=O)C(F)(F)F SQIIOMYKKDNKJQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 abstract description 19
- 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 abstract description 16
- 108010067306 Fibronectins Proteins 0.000 abstract description 12
- 102000016359 Fibronectins Human genes 0.000 abstract description 12
- 108010008212 Integrin alpha4beta1 Proteins 0.000 abstract description 12
- 230000003993 interaction Effects 0.000 abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 89
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 81
- 239000000243 solution Substances 0.000 description 73
- 238000006243 chemical reaction Methods 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
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- 150000002148 esters Chemical class 0.000 description 41
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
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- 125000001309 chloro group Chemical group Cl* 0.000 description 24
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 239000002585 base Substances 0.000 description 20
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
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- 238000001819 mass spectrum Methods 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
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- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
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- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000012256 powdered iron Substances 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
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- 230000000552 rheumatic effect Effects 0.000 description 1
- NZCRJKRKKOLAOJ-XRCRFVBUSA-N rifaximin Chemical compound OC1=C(C(O)=C2C)C3=C4N=C5C=C(C)C=CN5C4=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O NZCRJKRKKOLAOJ-XRCRFVBUSA-N 0.000 description 1
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- 235000009518 sodium iodide Nutrition 0.000 description 1
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- 235000010265 sodium sulphite Nutrition 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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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- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
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- 229940007718 zinc hydroxide Drugs 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Metal-Oxide And Bipolar Metal-Oxide Semiconductor Integrated Circuits (AREA)
- Semiconductor Integrated Circuits (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9908355.2A GB9908355D0 (en) | 1999-04-12 | 1999-04-12 | Chemical compounds |
| US14147099P | 1999-06-29 | 1999-06-29 | |
| PCT/GB2000/001393 WO2000061580A1 (en) | 1999-04-12 | 2000-04-12 | Substituted bicyclic heteroaryl compounds as integrin antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK14372001A3 true SK14372001A3 (sk) | 2002-06-04 |
Family
ID=26315408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1437-2001A SK14372001A3 (sk) | 1999-04-12 | 2000-04-12 | Substituované bicyklické heteroarylové zlúčeniny ako antagonisty integrínu a farmaceutický prostriedok, ktorý ich obsahuje |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6706738B2 (hr) |
| EP (1) | EP1183254B1 (hr) |
| KR (1) | KR20010110750A (hr) |
| CN (1) | CN1350534A (hr) |
| AT (1) | ATE286896T1 (hr) |
| AU (1) | AU769554B2 (hr) |
| BG (1) | BG106083A (hr) |
| BR (1) | BR0010599A (hr) |
| CA (1) | CA2369728A1 (hr) |
| CZ (1) | CZ20013661A3 (hr) |
| DE (1) | DE60017389T2 (hr) |
| EE (1) | EE200100528A (hr) |
| ES (1) | ES2231179T3 (hr) |
| HK (1) | HK1044937A1 (hr) |
| HR (1) | HRP20010732A2 (hr) |
| HU (1) | HUP0200803A3 (hr) |
| IL (2) | IL145748A0 (hr) |
| MX (1) | MXPA01010231A (hr) |
| NO (1) | NO20014951L (hr) |
| NZ (1) | NZ514602A (hr) |
| PL (1) | PL351433A1 (hr) |
| SK (1) | SK14372001A3 (hr) |
| TR (1) | TR200102959T2 (hr) |
| WO (1) | WO2000061580A1 (hr) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP4212358B2 (ja) | 2000-12-28 | 2009-01-21 | 第一三共株式会社 | Ｖｌａ−４阻害薬 |
| DE60329910D1 (de) * | 2002-03-29 | 2009-12-17 | Novartis Vaccines & Diagnostic | Substituierte benzazole und ihre verwendung als raf-kinase-hemmer |
| JP4676884B2 (ja) | 2003-07-24 | 2011-04-27 | 第一三共株式会社 | シクロヘキサンカルボン酸類 |
| WO2005073224A2 (en) | 2004-01-23 | 2005-08-11 | Amgen Inc | Quinoline quinazoline pyridine and pyrimidine counds and their use in the treatment of inflammation angiogenesis and cancer |
| TW200536851A (en) | 2004-01-23 | 2005-11-16 | Amgen Inc | Compounds and methods of use |
| MX2007001890A (es) * | 2004-08-16 | 2009-02-12 | Procter & Gamble | Compuestos de fenol 2-(amino sustituido)-5, 6-sustituido, composiciones de teñido que las comprenden y su uso. |
| DE102004041137A1 (de) * | 2004-08-25 | 2006-03-02 | Wella Ag | o-Aminophenol-Derivate und diese Verbindungen enthaltende Färbemittel |
| US7235688B1 (en) | 2004-11-04 | 2007-06-26 | University Of Notre Dame Du Lac | Process for preparing histone deacetylase inhibitors and intermediates thereof |
| US20070021612A1 (en) * | 2004-11-04 | 2007-01-25 | University Of Notre Dame Du Lac | Processes and compounds for preparing histone deacetylase inhibitors and intermediates thereof |
| EP1827434B1 (en) | 2004-11-30 | 2014-01-15 | Amgen Inc. | Quinolines and quinazoline analogs and their use as medicaments for treating cancer |
| US7514460B2 (en) | 2004-12-22 | 2009-04-07 | 4Sc Ag | Benzazole analogues and uses thereof |
| JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| TW200804345A (en) * | 2005-08-30 | 2008-01-16 | Novartis Ag | Substituted benzimidazoles and methods of preparation |
| PL2010528T3 (pl) | 2006-04-19 | 2018-03-30 | Novartis Ag | 6-0-podstawione związki benzoksazolowe i benzotiazolowe i sposoby hamowania sygnalizacji csf-1r |
| US7931838B2 (en) * | 2006-08-31 | 2011-04-26 | Virginia Tech Intellectual Properties, Inc. | Method for making oriented single-walled carbon nanotube/polymer nano-composite membranes |
| EP2220078B1 (en) * | 2007-10-29 | 2013-05-22 | Amgen, Inc | Benzomorpholine derivatives and methods of use |
| UY32138A (es) * | 2008-09-25 | 2010-04-30 | Boehringer Ingelheim Int | Amidas sustituidas del ácido 2-(2,6-dicloro-fenilamino)-6-fluoro-1-metil-1h-bencimidazol-5-carboxílico y sus sales farmacéuticamente aceptables |
| UY32470A (es) * | 2009-03-05 | 2010-10-29 | Boehringer Ingelheim Int | Derivados de 2-{2-cloro-5-[(sustituido) metil]fenilamino} -1-metil]fenilamino}-1-metilbencimidazol-5-carboxamidas-n-(sustituidas) y sus sales fisiológicamente aceptables, composiciones conteniéndolos y aplicaciones |
| US8759537B2 (en) | 2010-08-20 | 2014-06-24 | Boehringer Ingelheim International Gmbh | 3H-imidazo [4, 5-C] pyridine-6-carboxamides as anti-inflammatory agents |
| US8586604B2 (en) | 2010-08-20 | 2013-11-19 | Boehringer Ingelheim International Gmbh | Inhibitors of the microsomal prostaglandin E2 synthase-1 |
| US8466186B2 (en) | 2010-12-10 | 2013-06-18 | Boehringer Ingelheim International Gmbh | Compounds |
| US8486968B2 (en) | 2010-12-10 | 2013-07-16 | Boehringer Ingelheim International Gmbh | Compounds |
| US8674113B2 (en) | 2010-12-10 | 2014-03-18 | Boehringer Ingelheim International Gmbh | Compounds |
| US9273093B2 (en) | 2012-10-11 | 2016-03-01 | Protagonist Therapeutics, Inc. | α4β7 peptide dimer antagonists |
| LT2968443T (lt) | 2013-03-15 | 2021-12-10 | Protagonist Therapeutics, Inc. | Hepcidino analogai ir jų naudojimas |
| EP3960754A3 (en) * | 2014-05-16 | 2022-07-06 | Protagonist Therapeutics, Inc. | Alpha4beta7 integrin thioether peptide antagonists |
| RU2736637C9 (ru) | 2014-07-17 | 2021-02-08 | Протагонист Терепьютикс, Инк. | Пептидные ингибиторы рецептора интерлейкина-23 для перорального приема и их применение для лечения воспалительных заболеваний кишечника |
| EP3200812B8 (en) | 2014-10-01 | 2021-04-28 | Protagonist Therapeutics, Inc. | Novel alpha4beta7 peptide monomer and dimer antagonists |
| US10301371B2 (en) | 2014-10-01 | 2019-05-28 | Protagonist Therapeutics, Inc. | Cyclic monomer and dimer peptides having integrin antagonist activity |
| US10787490B2 (en) | 2015-07-15 | 2020-09-29 | Protaganist Therapeutics, Inc. | Peptide inhibitors of interleukin-23 receptor and their use to treat inflammatory diseases |
| CA3009834A1 (en) | 2015-12-30 | 2017-07-06 | Protagonist Therapeutics, Inc. | Analogues of hepcidin mimetics with improved in vivo half lives |
| US10407468B2 (en) | 2016-03-23 | 2019-09-10 | Protagonist Therapeutics, Inc. | Methods for synthesizing α4β7 peptide antagonists |
| TW201920234A (zh) | 2017-09-11 | 2019-06-01 | 美商領導醫療有限公司 | 類鴉片促效劑肽及其用途 |
| CA3089868A1 (en) | 2018-02-08 | 2019-08-15 | Protagonist Therapeutics, Inc. | Conjugated hepcidin mimetics |
| EP3997105A4 (en) | 2019-07-10 | 2023-09-13 | Protagonist Therapeutics, Inc. | PEPTIDE INHIBITORS OF THE INTERLEUKIN-23 RECEPTOR AND THEIR USE IN THE TREATMENT OF INFLAMMATORY DISEASES |
| WO2021146441A1 (en) | 2020-01-15 | 2021-07-22 | Janssen Biotech, Inc. | Peptide inhibitors of interleukin-23 receptor and their use to treat inflammatory diseases |
| CN115279782A (zh) | 2020-01-15 | 2022-11-01 | 詹森生物科技公司 | 白介素-23受体的肽抑制剂及其用于治疗炎性疾病的用途 |
| WO2021226261A1 (en) | 2020-05-06 | 2021-11-11 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| US11939361B2 (en) | 2020-11-20 | 2024-03-26 | Janssen Pharmaceutica Nv | Compositions of peptide inhibitors of Interleukin-23 receptor |
| TW202241889A (zh) | 2020-12-23 | 2022-11-01 | 美商雅捷可斯治療公司 | 作為ｊａｋ２抑制劑之６－雜芳基氧基苯并咪唑及氮雜苯并咪唑 |
| CA3234638A1 (en) | 2021-11-09 | 2023-05-19 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11510814A (ja) * | 1995-08-30 | 1999-09-21 | ジー．ディー．サール アンド カンパニー | インテグリンアンタゴニストとしてのメタ−グアニジン、尿素、チオ尿素またはアザ環状アミノ安息香酸誘導体 |
| IL138677A0 (en) * | 1998-04-10 | 2001-10-31 | Searle & Co | Heterocyclic glycyl beta-alanine derivatives as vitronectin antagonists |
| ATE325105T1 (de) * | 1999-02-16 | 2006-06-15 | Aventis Pharma Ltd | Bicyclische verbindungen und ihre verwendung als integrinrezeptorliganden |
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2000
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- 2000-04-12 MX MXPA01010231A patent/MXPA01010231A/es unknown
- 2000-04-12 EP EP00919064A patent/EP1183254B1/en not_active Expired - Lifetime
- 2000-04-12 PL PL00351433A patent/PL351433A1/xx not_active Application Discontinuation
- 2000-04-12 ES ES00919064T patent/ES2231179T3/es not_active Expired - Lifetime
- 2000-04-12 IL IL14574800A patent/IL145748A0/xx active IP Right Grant
- 2000-04-12 AU AU39816/00A patent/AU769554B2/en not_active Expired
- 2000-04-12 HU HU0200803A patent/HUP0200803A3/hu unknown
- 2000-04-12 EE EEP200100528A patent/EE200100528A/xx unknown
- 2000-04-12 WO PCT/GB2000/001393 patent/WO2000061580A1/en not_active Application Discontinuation
- 2000-04-12 CN CN00807512A patent/CN1350534A/zh active Pending
- 2000-04-12 BR BR0010599-6A patent/BR0010599A/pt not_active Application Discontinuation
- 2000-04-12 KR KR1020017013055A patent/KR20010110750A/ko not_active Application Discontinuation
- 2000-04-12 CZ CZ20013661A patent/CZ20013661A3/cs unknown
- 2000-04-12 SK SK1437-2001A patent/SK14372001A3/sk unknown
- 2000-04-12 CA CA002369728A patent/CA2369728A1/en not_active Abandoned
- 2000-04-12 DE DE60017389T patent/DE60017389T2/de not_active Expired - Lifetime
- 2000-04-12 NZ NZ514602A patent/NZ514602A/xx unknown
- 2000-04-12 AT AT00919064T patent/ATE286896T1/de not_active IP Right Cessation
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2001
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- 2001-10-10 HR HR20010732A patent/HRP20010732A2/hr not_active Application Discontinuation
- 2001-10-11 NO NO20014951A patent/NO20014951L/no not_active Application Discontinuation
- 2001-10-11 US US09/975,721 patent/US6706738B2/en not_active Expired - Lifetime
- 2001-11-05 BG BG106083A patent/BG106083A/xx unknown
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2002
- 2002-07-30 HK HK02105579.6A patent/HK1044937A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2369728A1 (en) | 2000-10-19 |
| BG106083A (en) | 2002-05-31 |
| PL351433A1 (en) | 2003-04-22 |
| NO20014951D0 (no) | 2001-10-11 |
| AU3981600A (en) | 2000-11-14 |
| AU769554B2 (en) | 2004-01-29 |
| TR200102959T2 (tr) | 2002-04-22 |
| HK1044937A1 (zh) | 2002-11-08 |
| US20020173506A1 (en) | 2002-11-21 |
| NZ514602A (en) | 2003-06-30 |
| HUP0200803A2 (hu) | 2002-07-29 |
| DE60017389T2 (de) | 2006-03-02 |
| EE200100528A (et) | 2003-02-17 |
| WO2000061580A1 (en) | 2000-10-19 |
| CZ20013661A3 (cs) | 2002-01-16 |
| BR0010599A (pt) | 2002-02-13 |
| ES2231179T3 (es) | 2005-05-16 |
| HRP20010732A2 (en) | 2002-12-31 |
| DE60017389D1 (de) | 2005-02-17 |
| CN1350534A (zh) | 2002-05-22 |
| NO20014951L (no) | 2001-12-11 |
| EP1183254A1 (en) | 2002-03-06 |
| IL145748A0 (en) | 2002-07-25 |
| IL145748A (en) | 2007-02-11 |
| EP1183254B1 (en) | 2005-01-12 |
| US6706738B2 (en) | 2004-03-16 |
| ATE286896T1 (de) | 2005-01-15 |
| MXPA01010231A (es) | 2003-07-21 |
| KR20010110750A (ko) | 2001-12-13 |
| HUP0200803A3 (en) | 2002-12-28 |
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