LT4535B - Tricikliai junginiai, pasižymintys specifiniu aktyvumu integrinams, būtent 3 integrinui, jų gavimo būdas, tarpiniai jungiai šiems junginiams gauti, jų panaudojimas vaistams ir farmacinės kompozicijos, į kurias įeina šie junginiai - Google Patents
Tricikliai junginiai, pasižymintys specifiniu aktyvumu integrinams, būtent 3 integrinui, jų gavimo būdas, tarpiniai jungiai šiems junginiams gauti, jų panaudojimas vaistams ir farmacinės kompozicijos, į kurias įeina šie junginiai Download PDFInfo
- Publication number
- LT4535B LT4535B LT98-145A LT98145A LT4535B LT 4535 B LT4535 B LT 4535B LT 98145 A LT98145 A LT 98145A LT 4535 B LT4535 B LT 4535B
- Authority
- LT
- Lithuania
- Prior art keywords
- formula
- benz
- dimethoxy
- azulenyl
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 129
- 238000000034 method Methods 0.000 title claims description 35
- 239000000543 intermediate Substances 0.000 title claims description 11
- 239000003814 drug Substances 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 102000006495 integrins Human genes 0.000 title description 9
- 108010044426 integrins Proteins 0.000 title description 9
- 230000000694 effects Effects 0.000 title description 5
- 229940079593 drug Drugs 0.000 title 1
- -1 hydroxy, amino Chemical group 0.000 claims description 176
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 150000007857 hydrazones Chemical class 0.000 claims description 39
- 150000002148 esters Chemical class 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000002585 base Substances 0.000 claims description 33
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000003828 azulenyl group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 150000007513 acids Chemical class 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
- 239000003153 chemical reaction reagent Substances 0.000 claims description 23
- 125000005638 hydrazono group Chemical group 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 239000011593 sulfur Chemical group 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000000903 blocking effect Effects 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 150000002009 diols Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000002609 medium Substances 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052705 radium Inorganic materials 0.000 claims description 8
- 229910052702 rhenium Inorganic materials 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 7
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000006900 dealkylation reaction Methods 0.000 claims description 6
- 239000012351 deprotecting agent Substances 0.000 claims description 6
- 230000002140 halogenating effect Effects 0.000 claims description 6
- 229910052703 rhodium Inorganic materials 0.000 claims description 6
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 6
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 6
- LFQGAXHACYZOEZ-UHFFFAOYSA-N 10-hydroxy-8,9-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-4-one Chemical compound C1=2C(O)=C(OC)C(OC)=CC=2CCC(=O)C2=C1CCC2 LFQGAXHACYZOEZ-UHFFFAOYSA-N 0.000 claims description 5
- NRKDVEVDYBDVKS-UHFFFAOYSA-N 8-hydroxy-9,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-4-one Chemical compound C12=C(OC)C(OC)=C(O)C=C2CCC(=O)C2=C1CCC2 NRKDVEVDYBDVKS-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910003827 NRaRb Inorganic materials 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 230000020335 dealkylation Effects 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 claims description 4
- AOVYTDOKKSSUQE-UHFFFAOYSA-N 7-[[4-(methanehydrazonoylhydrazinylidene)-9,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-8-yl]oxy]heptanoic acid Chemical compound C12=C(OC)C(OC)=C(OCCCCCCC(O)=O)C=C2CCC(=NNC=NN)C2=C1CCC2 AOVYTDOKKSSUQE-UHFFFAOYSA-N 0.000 claims description 4
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 239000002981 blocking agent Substances 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 238000010511 deprotection reaction Methods 0.000 claims description 4
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 4
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 4
- WEOLHZQIXNLINQ-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)-9,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-8-yl]oxy]-2-[3-(4-pyridin-3-ylimidazol-1-yl)propoxycarbonylamino]butanoic acid Chemical compound C1=C2CCC(=NNC=3NCCN=3)C(CCC3)=C3C2=C(OC)C(OC)=C1OCCC(C(O)=O)NC(=O)OCCCN(C=1)C=NC=1C1=CC=CN=C1 WEOLHZQIXNLINQ-UHFFFAOYSA-N 0.000 claims description 3
- QKCFQUGEKKDAIG-UHFFFAOYSA-N 5-[[4-(methanehydrazonoylhydrazinylidene)-8,9-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-10-yl]oxy]pentanoic acid Chemical compound C1=2C(OCCCCC(O)=O)=C(OC)C(OC)=CC=2CCC(=NNC=NN)C2=C1CCC2 QKCFQUGEKKDAIG-UHFFFAOYSA-N 0.000 claims description 3
- 150000008574 D-amino acids Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 150000001266 acyl halides Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000004419 alkynylene group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 238000006703 hydration reaction Methods 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 230000036961 partial effect Effects 0.000 claims description 3
- GODHIFXMNKQHEI-UHFFFAOYSA-N pentanoic acid;hydrochloride Chemical compound Cl.CCCCC(O)=O GODHIFXMNKQHEI-UHFFFAOYSA-N 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- VGGAROHFTJSSNT-UHFFFAOYSA-N 2-[[4-(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)-9,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-8-yl]oxy]acetic acid Chemical compound C1CCC2=C1C1=C(OC)C(OC)=C(OCC(O)=O)C=C1CCC2=NNC1=NCCN1 VGGAROHFTJSSNT-UHFFFAOYSA-N 0.000 claims description 2
- FVIBVGDZSWMSDR-UHFFFAOYSA-N 4-[[4-(methanehydrazonoylhydrazinylidene)-8,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-9-yl]oxy]butanoic acid Chemical compound C1=2C(OC)=C(OCCCC(O)=O)C(OC)=CC=2CCC(=NNC=NN)C2=C1CCC2 FVIBVGDZSWMSDR-UHFFFAOYSA-N 0.000 claims description 2
- VFSGJGRMPNSURL-UHFFFAOYSA-N 4-[[4-(methanehydrazonoylhydrazinylidene)-8,9-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-10-yl]oxy]butanoic acid Chemical compound C1=2C(OCCCC(O)=O)=C(OC)C(OC)=CC=2CCC(=NNC=NN)C2=C1CCC2 VFSGJGRMPNSURL-UHFFFAOYSA-N 0.000 claims description 2
- DSOLPLDLMQLCKK-UHFFFAOYSA-N 4-[[4-(methanehydrazonoylhydrazinylidene)-9,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-8-yl]oxy]butanoic acid Chemical compound C12=C(OC)C(OC)=C(OCCCC(O)=O)C=C2CCC(=NNC=NN)C2=C1CCC2 DSOLPLDLMQLCKK-UHFFFAOYSA-N 0.000 claims description 2
- YKXIXNZZLKAGDC-UHFFFAOYSA-N 5-[[4-(carbamothioylhydrazinylidene)-9,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-8-yl]oxy]pentanoic acid Chemical compound C12=C(OC)C(OC)=C(OCCCCC(O)=O)C=C2CCC(=NNC(N)=S)C2=C1CCC2 YKXIXNZZLKAGDC-UHFFFAOYSA-N 0.000 claims description 2
- DIHJYCFHNDFVIC-UHFFFAOYSA-N 5-[[4-(carbamoylhydrazinylidene)-9,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-8-yl]oxy]pentanoic acid Chemical compound C12=C(OC)C(OC)=C(OCCCCC(O)=O)C=C2CCC(=NNC(N)=O)C2=C1CCC2 DIHJYCFHNDFVIC-UHFFFAOYSA-N 0.000 claims description 2
- LHRRAGKVTFIVHE-UHFFFAOYSA-N 5-[[4-(methanehydrazonoylhydrazinylidene)-8,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-9-yl]oxy]pentanoic acid Chemical compound C1=2C(OC)=C(OCCCCC(O)=O)C(OC)=CC=2CCC(=NNC=NN)C2=C1CCC2 LHRRAGKVTFIVHE-UHFFFAOYSA-N 0.000 claims description 2
- SILZKNNDBWRLTC-UHFFFAOYSA-N 6-[[4-(methanehydrazonoylhydrazinylidene)-9,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-8-yl]oxy]hexanoic acid Chemical compound C12=C(OC)C(OC)=C(OCCCCCC(O)=O)C=C2CCC(=NNC=NN)C2=C1CCC2 SILZKNNDBWRLTC-UHFFFAOYSA-N 0.000 claims description 2
- DYRAZYPILFDGCD-UHFFFAOYSA-N Cl.CCCCC(=O)OCC Chemical compound Cl.CCCCC(=O)OCC DYRAZYPILFDGCD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000012374 esterification agent Substances 0.000 claims description 2
- 230000036571 hydration Effects 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 230000020176 deacylation Effects 0.000 claims 2
- 238000005947 deacylation reaction Methods 0.000 claims 2
- XAOCQVQWFNUKBR-UHFFFAOYSA-N 4-[[4-(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)-9,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-8-yl]oxy]butanoic acid Chemical compound C1CCC2=C1C1=C(OC)C(OC)=C(OCCCC(O)=O)C=C1CCC2=NNC1=NCCN1 XAOCQVQWFNUKBR-UHFFFAOYSA-N 0.000 claims 1
- PJZPXZRMLYZYRN-UHFFFAOYSA-N 5-[[4-(methanehydrazonoylhydrazinylidene)-9,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-8-yl]oxy]-3,3-dimethyl-4-oxopentanoic acid Chemical compound C12=C(OC)C(OC)=C(OCC(=O)C(C)(C)CC(O)=O)C=C2CCC(=NNC=NN)C2=C1CCC2 PJZPXZRMLYZYRN-UHFFFAOYSA-N 0.000 claims 1
- VNEYTHGVCKGBMM-UHFFFAOYSA-N 5-[[9,10-dimethoxy-4-[(5-oxo-1,4-dihydroimidazol-2-yl)hydrazinylidene]-2,3,5,6-tetrahydro-1h-benzo[e]azulen-8-yl]oxy]pentanoic acid Chemical compound C1CCC2=C1C1=C(OC)C(OC)=C(OCCCCC(O)=O)C=C1CCC2=NNC1=NCC(=O)N1 VNEYTHGVCKGBMM-UHFFFAOYSA-N 0.000 claims 1
- XYGPFVUDUMXBLB-UHFFFAOYSA-N 6-[[4-(4,5-dihydro-1h-imidazol-2-ylhydrazinylidene)-9,10-dimethoxy-2,3,5,6-tetrahydro-1h-benzo[e]azulen-8-yl]oxy]hexanoic acid Chemical compound C1CCC2=C1C1=C(OC)C(OC)=C(OCCCCCC(O)=O)C=C1CCC2=NNC1=NCCN1 XYGPFVUDUMXBLB-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 148
- 239000000047 product Substances 0.000 description 130
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 128
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- 230000002829 reductive effect Effects 0.000 description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 43
- 150000003254 radicals Chemical class 0.000 description 41
- 239000000243 solution Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 36
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- 239000002904 solvent Substances 0.000 description 29
- 239000000203 mixture Substances 0.000 description 27
- 238000003756 stirring Methods 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000000377 silicon dioxide Substances 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 229910021529 ammonia Inorganic materials 0.000 description 18
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 17
- 239000012043 crude product Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000004587 chromatography analysis Methods 0.000 description 15
- 238000011282 treatment Methods 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
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- 230000024279 bone resorption Effects 0.000 description 11
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
- 239000000872 buffer Substances 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 239000011575 calcium Substances 0.000 description 9
- 210000002997 osteoclast Anatomy 0.000 description 9
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- 239000003446 ligand Substances 0.000 description 8
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- 238000012360 testing method Methods 0.000 description 8
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 239000010948 rhodium Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 6
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
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- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000003998 snake venom Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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- 239000000829 suppository Substances 0.000 description 1
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- IWVMCIAPBOORJL-UHFFFAOYSA-N thieno[2,3-b]furan Chemical compound C1=CSC2=C1C=CO2 IWVMCIAPBOORJL-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 108091007466 transmembrane glycoproteins Proteins 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- CIWZUQUKZAMSIZ-UHFFFAOYSA-N trimethoxy borate Chemical compound COOB(OOC)OOC CIWZUQUKZAMSIZ-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 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
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/18—Nitrogen atoms not forming part of a nitro radical with hetero atoms attached to said nitrogen atoms, except nitro radicals, e.g. hydrazine radicals
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
- C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
- C07C281/12—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being part of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/04—Thiocyanates having sulfur atoms of thiocyanate groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/10—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/12—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/14—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C337/06—Compounds containing any of the groups, e.g. thiosemicarbazides
- C07C337/08—Compounds containing any of the groups, e.g. thiosemicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. thiosemicarbazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
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- 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
- C07D233/52—Nitrogen atoms not forming part of a nitro radical with hetero atoms directly attached to said nitrogen atoms
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- 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
- C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9603437A FR2746394B1 (fr) | 1996-03-20 | 1996-03-20 | Nouveaux composes tricycliques, leur procede de preparation, et les intermediaires de ce procede, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LT98145A LT98145A (en) | 1999-03-25 |
| LT4535B true LT4535B (lt) | 1999-08-25 |
Family
ID=9490337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LT98-145A LT4535B (lt) | 1996-03-20 | 1998-10-15 | Tricikliai junginiai, pasižymintys specifiniu aktyvumu integrinams, būtent 3 integrinui, jų gavimo būdas, tarpiniai jungiai šiems junginiams gauti, jų panaudojimas vaistams ir farmacinės kompozicijos, į kurias įeina šie junginiai |
Country Status (16)
| Country | Link |
|---|---|
| CN (2) | CN1090178C (fr) |
| AR (1) | AR006317A1 (fr) |
| CZ (1) | CZ288898A3 (fr) |
| ES (1) | ES2164337T3 (fr) |
| FR (1) | FR2746394B1 (fr) |
| HR (1) | HRP970163A2 (fr) |
| HU (1) | HUP9902495A3 (fr) |
| IL (1) | IL126106A0 (fr) |
| LT (1) | LT4535B (fr) |
| OA (1) | OA11603A (fr) |
| PL (1) | PL329034A1 (fr) |
| PT (1) | PT888292E (fr) |
| TR (1) | TR199801846T2 (fr) |
| TW (1) | TW458963B (fr) |
| YU (1) | YU40898A (fr) |
| ZA (1) | ZA972393B (fr) |
Citations (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0029488A1 (fr) | 1979-09-19 | 1981-06-03 | Hoechst Aktiengesellschaft | Dérivés d'amino-acides, procédé pour leur préparation et leur utilisation pour le traitement de l'hypertension |
| EP0031741A1 (fr) | 1979-12-07 | 1981-07-08 | SCIENCE UNION ET Cie SOCIETE FRANCAISE DE RECHERCHE MEDICALE | Nouveaux iminoacides substitués, leurs procédés de préparation et leur emploi comme inhibiteurs d'enzymes |
| EP0046953A2 (fr) | 1980-08-30 | 1982-03-10 | Hoechst Aktiengesellschaft | Dérivés des acides aminés, leurs procédés de préparation, compositions les contenant et leur application |
| EP0049605A1 (fr) | 1980-10-03 | 1982-04-14 | Warner-Lambert Company | Dérivés acyl-substitués de l'acide 1,2,3,4-tétrahydroisoquinoline-3-carboxylique, leurs sels, compositions pharmaceutiques les contenant et leur préparation |
| EP0049658A1 (fr) | 1980-10-02 | 1982-04-14 | Adir | Iminodiacides substitués, leur préparation et compositions pharmaceutiques les contenant |
| EP0051020A1 (fr) | 1980-10-21 | 1982-05-05 | Adir | Acides aza bicyclooctane carboxyliques, leur préparation et compositions pharmaceutiques les contenant |
| EP0050800A1 (fr) | 1980-10-23 | 1982-05-05 | Schering Corporation | Dipeptides carboxyalcoyliques, procédés pour les préparer et compositions pharmaceutiques les contenant |
| EP0052870A1 (fr) | 1980-11-25 | 1982-06-02 | Hoechst Aktiengesellschaft | Dérivés d'amino-acides et leurs procédés de préparation |
| US4350704A (en) | 1980-10-06 | 1982-09-21 | Warner-Lambert Company | Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids |
| US4374847A (en) | 1980-10-27 | 1983-02-22 | Ciba-Geigy Corporation | 1-Carboxyalkanoylindoline-2-carboxylic acids |
| EP0079022A2 (fr) | 1981-11-05 | 1983-05-18 | Hoechst Aktiengesellschaft | Dérivés de l'acide cis, endo-2-azabicyclo-(3.3.0)-octane-3-carboxylique, procédé pour leur préparation, medicaments les contenant et leur application |
| EP0084164A2 (fr) | 1981-12-29 | 1983-07-27 | Hoechst Aktiengesellschaft | Dérivés d'amino-acides bicycliques, procédé pour leur préparation, agents les contenant et leur utilisation ainsi que des amino-acides bicycliques comme intermédiaires et procédé pour leur préparation |
| EP0089637A2 (fr) | 1982-03-23 | 1983-09-28 | Hoechst Aktiengesellschaft | Dérivés d'amino acides bicycliques, procédé pour leur préparation, agents les contenant et leur utilisation, ainsi que des amino acides bicycliques comme produits intermédiaires et procédé pour leur préparation |
| EP0090362A2 (fr) | 1982-03-30 | 1983-10-05 | Hoechst Aktiengesellschaft | Dérivés des acides cycloalka(c)pyrrol carboxyliques, leur procédé de préparation, les agents les contenant, leur emploi, les acides cycloalka(c)pyrrol carboxyliques comme intermédiaires et leur procédé de préparation |
| EP0090341A2 (fr) | 1982-03-27 | 1983-10-05 | Hoechst Aktiengesellschaft | Dérivés des acides spiro(4,(3+n))-2-aza-alcan-3-carboxyliques, leur procédé de préparation, les agents les contenant et leur emploi |
| EP0105102A1 (fr) | 1982-07-20 | 1984-04-11 | Hoechst Aktiengesellschaft | Dérivés d'acides 2-aza-bicyclo(2,2,2)-octane-3-carboxyliques, leur procédé de préparation, les médicaments les contenant et leur application, ainsi que l'acide 2-aza-bicyclo(2,2,2)-octane-3-carboxylique comme intermédiaire et le procédé pour sa préparation |
| EP0109020A2 (fr) | 1982-11-13 | 1984-05-23 | Hoechst Aktiengesellschaft | Dérivés d'amino-acides tricycliques, leur procédé de préparation, les composés les contenant, leur emploi, et les amino-acides bicycliques comme intermédiaires et leur procédé de préparation |
| EP0111873A1 (fr) | 1982-12-16 | 1984-06-27 | Hoechst Aktiengesellschaft | Dérivés de l'acide cis, endo-aza-2 bicyclo(5.3.0)décane-carboxylique-3, procédé pour leur préparation, compositions les contenant et leur application |
| EP0271865A2 (fr) | 1986-12-17 | 1988-06-22 | Hoechst Aktiengesellschaft | Isoxazolidines 2,3-disubstituées leur procédé de préparation les agents les contenant et leur emploi |
| EP0344682A2 (fr) | 1988-06-03 | 1989-12-06 | Hoechst Aktiengesellschaft | Oligopeptides contenant des analogues cycliques d'amino-acides de proline |
| EP0729933A1 (fr) | 1995-03-03 | 1996-09-04 | Roussel-Uclaf | Dérivés tricycliques, leur préparation et leur application à la préparation de la colchicine et de la thiocolchicine optiquement actives ou racémiques et d'analogues ou dérivés et intermédiaires |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10504825A (ja) * | 1994-08-22 | 1998-05-12 | スミスクライン・ビーチャム・コーポレイション | 二環式化合物 |
-
1996
- 1996-03-20 FR FR9603437A patent/FR2746394B1/fr not_active Expired - Lifetime
-
1997
- 1997-03-19 AR ARP970101095A patent/AR006317A1/es unknown
- 1997-03-19 ZA ZA9702393A patent/ZA972393B/xx unknown
- 1997-03-19 HR HR9603437A patent/HRP970163A2/hr not_active Application Discontinuation
- 1997-03-20 PL PL97329034A patent/PL329034A1/xx unknown
- 1997-03-20 CZ CZ982888A patent/CZ288898A3/cs unknown
- 1997-03-20 CN CN97194806A patent/CN1090178C/zh not_active Expired - Fee Related
- 1997-03-20 IL IL12610697A patent/IL126106A0/xx unknown
- 1997-03-20 ES ES97915519T patent/ES2164337T3/es not_active Expired - Lifetime
- 1997-03-20 PT PT97915519T patent/PT888292E/pt unknown
- 1997-03-20 TR TR1998/01846T patent/TR199801846T2/xx unknown
- 1997-03-20 HU HU9902495A patent/HUP9902495A3/hu unknown
- 1997-09-23 TW TW086113848A patent/TW458963B/zh not_active IP Right Cessation
-
1998
- 1998-09-18 YU YU40898A patent/YU40898A/sh unknown
- 1998-09-18 OA OA9800175A patent/OA11603A/fr unknown
- 1998-10-15 LT LT98-145A patent/LT4535B/lt not_active IP Right Cessation
-
2002
- 2002-06-27 CN CN02141265A patent/CN1401621A/zh active Pending
Patent Citations (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0029488A1 (fr) | 1979-09-19 | 1981-06-03 | Hoechst Aktiengesellschaft | Dérivés d'amino-acides, procédé pour leur préparation et leur utilisation pour le traitement de l'hypertension |
| EP0031741A1 (fr) | 1979-12-07 | 1981-07-08 | SCIENCE UNION ET Cie SOCIETE FRANCAISE DE RECHERCHE MEDICALE | Nouveaux iminoacides substitués, leurs procédés de préparation et leur emploi comme inhibiteurs d'enzymes |
| EP0046953A2 (fr) | 1980-08-30 | 1982-03-10 | Hoechst Aktiengesellschaft | Dérivés des acides aminés, leurs procédés de préparation, compositions les contenant et leur application |
| EP0049658A1 (fr) | 1980-10-02 | 1982-04-14 | Adir | Iminodiacides substitués, leur préparation et compositions pharmaceutiques les contenant |
| EP0049605A1 (fr) | 1980-10-03 | 1982-04-14 | Warner-Lambert Company | Dérivés acyl-substitués de l'acide 1,2,3,4-tétrahydroisoquinoline-3-carboxylique, leurs sels, compositions pharmaceutiques les contenant et leur préparation |
| US4344949A (en) | 1980-10-03 | 1982-08-17 | Warner-Lambert Company | Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids |
| US4350704A (en) | 1980-10-06 | 1982-09-21 | Warner-Lambert Company | Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids |
| EP0051020A1 (fr) | 1980-10-21 | 1982-05-05 | Adir | Acides aza bicyclooctane carboxyliques, leur préparation et compositions pharmaceutiques les contenant |
| EP0050800A1 (fr) | 1980-10-23 | 1982-05-05 | Schering Corporation | Dipeptides carboxyalcoyliques, procédés pour les préparer et compositions pharmaceutiques les contenant |
| US4374847A (en) | 1980-10-27 | 1983-02-22 | Ciba-Geigy Corporation | 1-Carboxyalkanoylindoline-2-carboxylic acids |
| EP0052870A1 (fr) | 1980-11-25 | 1982-06-02 | Hoechst Aktiengesellschaft | Dérivés d'amino-acides et leurs procédés de préparation |
| EP0079022A2 (fr) | 1981-11-05 | 1983-05-18 | Hoechst Aktiengesellschaft | Dérivés de l'acide cis, endo-2-azabicyclo-(3.3.0)-octane-3-carboxylique, procédé pour leur préparation, medicaments les contenant et leur application |
| EP0084164A2 (fr) | 1981-12-29 | 1983-07-27 | Hoechst Aktiengesellschaft | Dérivés d'amino-acides bicycliques, procédé pour leur préparation, agents les contenant et leur utilisation ainsi que des amino-acides bicycliques comme intermédiaires et procédé pour leur préparation |
| EP0089637A2 (fr) | 1982-03-23 | 1983-09-28 | Hoechst Aktiengesellschaft | Dérivés d'amino acides bicycliques, procédé pour leur préparation, agents les contenant et leur utilisation, ainsi que des amino acides bicycliques comme produits intermédiaires et procédé pour leur préparation |
| EP0090341A2 (fr) | 1982-03-27 | 1983-10-05 | Hoechst Aktiengesellschaft | Dérivés des acides spiro(4,(3+n))-2-aza-alcan-3-carboxyliques, leur procédé de préparation, les agents les contenant et leur emploi |
| EP0090362A2 (fr) | 1982-03-30 | 1983-10-05 | Hoechst Aktiengesellschaft | Dérivés des acides cycloalka(c)pyrrol carboxyliques, leur procédé de préparation, les agents les contenant, leur emploi, les acides cycloalka(c)pyrrol carboxyliques comme intermédiaires et leur procédé de préparation |
| EP0105102A1 (fr) | 1982-07-20 | 1984-04-11 | Hoechst Aktiengesellschaft | Dérivés d'acides 2-aza-bicyclo(2,2,2)-octane-3-carboxyliques, leur procédé de préparation, les médicaments les contenant et leur application, ainsi que l'acide 2-aza-bicyclo(2,2,2)-octane-3-carboxylique comme intermédiaire et le procédé pour sa préparation |
| EP0109020A2 (fr) | 1982-11-13 | 1984-05-23 | Hoechst Aktiengesellschaft | Dérivés d'amino-acides tricycliques, leur procédé de préparation, les composés les contenant, leur emploi, et les amino-acides bicycliques comme intermédiaires et leur procédé de préparation |
| EP0111873A1 (fr) | 1982-12-16 | 1984-06-27 | Hoechst Aktiengesellschaft | Dérivés de l'acide cis, endo-aza-2 bicyclo(5.3.0)décane-carboxylique-3, procédé pour leur préparation, compositions les contenant et leur application |
| EP0271865A2 (fr) | 1986-12-17 | 1988-06-22 | Hoechst Aktiengesellschaft | Isoxazolidines 2,3-disubstituées leur procédé de préparation les agents les contenant et leur emploi |
| EP0344682A2 (fr) | 1988-06-03 | 1989-12-06 | Hoechst Aktiengesellschaft | Oligopeptides contenant des analogues cycliques d'amino-acides de proline |
| EP0729933A1 (fr) | 1995-03-03 | 1996-09-04 | Roussel-Uclaf | Dérivés tricycliques, leur préparation et leur application à la préparation de la colchicine et de la thiocolchicine optiquement actives ou racémiques et d'analogues ou dérivés et intermédiaires |
Non-Patent Citations (4)
| Title |
|---|
| BROOKS PC ET AL.: "Integrin alpha v beta 3 antagonists promote tumor regression by inducing apoptosis of angiogenic blood vessels", CELL, 1994, pages 1157 |
| HORTON MA, TAYLOR ML, ARNETT TR, HELFRICH MH.: "Arg-Gly-Asp (RGD) peptides and the anti-vitronectin receptor antibody 23C6 inhibit dentine resorption and cell spreading by osteoclasts", EXP CELL RES., 1991, pages 368, XP024791657, DOI: doi:10.1016/0014-4827(91)90386-9 |
| SATO M ET AL.: "Echistatin is a potent inhibitor of bone resorption in culture", J. CELL BIOL., 1990, pages 1713, XP000283175, DOI: doi:10.1083/jcb.111.4.1713 |
| STEVEN L BROWN ET AL.: "Stimulation of migration of human aortic smooth muscle cells by vitronectin: implications for atherosclerosis", CARDIOVASCULAR RESEARCH, 1994, pages 1815, XP000864367, DOI: doi:10.1093/cvr/28.12.1815 |
Also Published As
| Publication number | Publication date |
|---|---|
| PT888292E (pt) | 2002-04-29 |
| OA11603A (fr) | 2004-08-11 |
| HUP9902495A3 (en) | 2001-07-30 |
| IL126106A0 (en) | 1999-05-09 |
| HUP9902495A2 (hu) | 1999-11-29 |
| AR006317A1 (es) | 1999-08-25 |
| YU40898A (sh) | 1999-09-27 |
| HRP970163A2 (en) | 1998-08-31 |
| TW458963B (en) | 2001-10-11 |
| CN1090178C (zh) | 2002-09-04 |
| ZA972393B (en) | 1998-03-19 |
| CN1219165A (zh) | 1999-06-09 |
| CN1401621A (zh) | 2003-03-12 |
| FR2746394B1 (fr) | 1998-05-29 |
| CZ288898A3 (cs) | 1999-03-17 |
| ES2164337T3 (es) | 2002-02-16 |
| LT98145A (en) | 1999-03-25 |
| TR199801846T2 (xx) | 1998-12-21 |
| PL329034A1 (en) | 1999-03-01 |
| FR2746394A1 (fr) | 1997-09-26 |
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