JP2004523583A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2004523583A5 JP2004523583A5 JP2002573760A JP2002573760A JP2004523583A5 JP 2004523583 A5 JP2004523583 A5 JP 2004523583A5 JP 2002573760 A JP2002573760 A JP 2002573760A JP 2002573760 A JP2002573760 A JP 2002573760A JP 2004523583 A5 JP2004523583 A5 JP 2004523583A5
- Authority
- JP
- Japan
- Prior art keywords
- dione
- sulfonyl
- pyrrolidin
- phenyl
- compound
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- XEWXWHHHHNZECJ-UHFFFAOYSA-N 4-[4-[2-(4-methyl-2,5-dioxoimidazolidin-4-yl)pyrrolidin-1-yl]sulfonylphenoxy]benzonitrile Chemical compound C1CCN(S(=O)(=O)C=2C=CC(OC=3C=CC(=CC=3)C#N)=CC=2)C1C1(C)NC(=O)NC1=O XEWXWHHHHNZECJ-UHFFFAOYSA-N 0.000 claims description 2
- NDTLBAGZBAWUGN-UHFFFAOYSA-N 5-[1-[4-(4-fluorophenoxy)phenyl]sulfonylpyrrolidin-2-yl]imidazolidine-2,4-dione Chemical compound C1=CC(F)=CC=C1OC1=CC=C(S(=O)(=O)N2C(CCC2)C2C(NC(=O)N2)=O)C=C1 NDTLBAGZBAWUGN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 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 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000006413 ring segment Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- JGSLKNWXPRDWBA-UHFFFAOYSA-N 2-methylidene-1h-pyridine Chemical compound C=C1NC=CC=C1 JGSLKNWXPRDWBA-UHFFFAOYSA-N 0.000 claims 1
- HQOYLKMNTYJZHI-UHFFFAOYSA-N 4-[4-[2-(2,5-dioxoimidazolidin-4-yl)pyrrolidin-1-yl]sulfonylphenoxy]benzonitrile Chemical compound O=C1NC(=O)NC1C1N(S(=O)(=O)C=2C=CC(OC=3C=CC(=CC=3)C#N)=CC=2)CCC1 HQOYLKMNTYJZHI-UHFFFAOYSA-N 0.000 claims 1
- VIEDTKMTRPGNAJ-UHFFFAOYSA-N 5-[1-[4-(4-chlorophenoxy)phenyl]sulfonylpyrrolidin-2-yl]-5-methylimidazolidine-2,4-dione Chemical compound C1CCN(S(=O)(=O)C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)C1C1(C)NC(=O)NC1=O VIEDTKMTRPGNAJ-UHFFFAOYSA-N 0.000 claims 1
- YGVNRRJRQIJHOF-UHFFFAOYSA-N 5-[1-[4-(4-chlorophenoxy)phenyl]sulfonylpyrrolidin-2-yl]imidazolidine-2,4-dione Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(S(=O)(=O)N2C(CCC2)C2C(NC(=O)N2)=O)C=C1 YGVNRRJRQIJHOF-UHFFFAOYSA-N 0.000 claims 1
- WSDIIUVUUSBUSU-UHFFFAOYSA-N 5-[1-[4-(4-fluorophenoxy)phenyl]sulfonylpyrrolidin-2-yl]-5-methylimidazolidine-2,4-dione Chemical compound C1CCN(S(=O)(=O)C=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)C1C1(C)NC(=O)NC1=O WSDIIUVUUSBUSU-UHFFFAOYSA-N 0.000 claims 1
- GHXNGDKPURNFHR-UHFFFAOYSA-N 5-[1-[4-(4-methoxyphenoxy)phenyl]sulfonylpyrrolidin-2-yl]-5-methylimidazolidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(S(=O)(=O)N2C(CCC2)C2(C)C(NC(=O)N2)=O)C=C1 GHXNGDKPURNFHR-UHFFFAOYSA-N 0.000 claims 1
- XIMHLBPAEFVGSV-UHFFFAOYSA-N 5-[1-[4-(4-methoxyphenoxy)phenyl]sulfonylpyrrolidin-2-yl]imidazolidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(S(=O)(=O)N2C(CCC2)C2C(NC(=O)N2)=O)C=C1 XIMHLBPAEFVGSV-UHFFFAOYSA-N 0.000 claims 1
- IQXBNGUCOFRPEJ-UHFFFAOYSA-N 5-[1-[4-(4-methylphenoxy)phenyl]sulfonylpyrrolidin-2-yl]imidazolidine-2,4-dione Chemical compound C1=CC(C)=CC=C1OC1=CC=C(S(=O)(=O)N2C(CCC2)C2C(NC(=O)N2)=O)C=C1 IQXBNGUCOFRPEJ-UHFFFAOYSA-N 0.000 claims 1
- RVKIHHFRMVLVQB-UHFFFAOYSA-N 5-methyl-5-[1-[4-(4-methylphenoxy)phenyl]sulfonylpyrrolidin-2-yl]imidazolidine-2,4-dione Chemical compound C1=CC(C)=CC=C1OC1=CC=C(S(=O)(=O)N2C(CCC2)C2(C)C(NC(=O)N2)=O)C=C1 RVKIHHFRMVLVQB-UHFFFAOYSA-N 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
- -1 guanidino, N-cyano-guanidino, thioguanidino Chemical group 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 3
- 229940091173 hydantoin Drugs 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 102000004506 Blood Proteins Human genes 0.000 description 2
- 108010017384 Blood Proteins Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102000005741 Metalloproteases Human genes 0.000 description 2
- 108010006035 Metalloproteases Proteins 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 235000012501 ammonium carbonate Nutrition 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- MXBPKCDCMFRWPS-AVJNFUFQSA-N (5s)-5-(benzylsulfanylmethyl)-5-methylimidazolidine-2,4-dione;[(4s)-4-methyl-2,5-dioxoimidazolidin-4-yl]methanesulfonyl chloride Chemical compound ClS(=O)(=O)C[C@@]1(C)NC(=O)NC1=O.C=1C=CC=CC=1CSC[C@@]1(C)NC(=O)NC1=O MXBPKCDCMFRWPS-AVJNFUFQSA-N 0.000 description 1
- KJORWTUTCOHCSK-UHFFFAOYSA-N 4-(3,5-dichlorophenoxy)-n-[(2,5-dioxoimidazolidin-4-yl)methyl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(OC=2C=CC(=CC=2)S(=O)(=O)NCC2C(NC(=O)N2)=O)=C1 KJORWTUTCOHCSK-UHFFFAOYSA-N 0.000 description 1
- XRJYDANYCFGNOM-UHFFFAOYSA-N 4-(4-chlorophenoxy)-n-[(2,5-dioxoimidazolidin-4-yl)methyl]-n-propan-2-ylbenzenesulfonamide Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)N(C(C)C)CC1NC(=O)NC1=O XRJYDANYCFGNOM-UHFFFAOYSA-N 0.000 description 1
- IXBZJPOQTSAQHW-UHFFFAOYSA-N 4-phenylbutane-2-thione Chemical compound CC(=S)CCC1=CC=CC=C1 IXBZJPOQTSAQHW-UHFFFAOYSA-N 0.000 description 1
- QDXMWEMIYNOVGF-UHFFFAOYSA-N 5-(benzylsulfanylmethyl)-5-methylimidazolidine-2,4-dione Chemical compound C=1C=CC=CC=1CSCC1(C)NC(=O)NC1=O QDXMWEMIYNOVGF-UHFFFAOYSA-N 0.000 description 1
- 241000699662 Cricetomys gambianus Species 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000005157 alkyl carboxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012131 assay buffer Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 241001515942 marmosets Species 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- MKONDSPRGHUOQT-UHFFFAOYSA-N n-[(2,5-dioxoimidazolidin-4-yl)methyl]-3-(4-methoxyphenoxy)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1OC1=CC=CC(S(=O)(=O)NCC2C(NC(=O)N2)=O)=C1 MKONDSPRGHUOQT-UHFFFAOYSA-N 0.000 description 1
- GEORCJMYOQHATJ-UHFFFAOYSA-N n-[(2,5-dioxoimidazolidin-4-yl)methyl]-4-(4-fluorophenyl)benzenesulfonamide Chemical compound C1=CC(F)=CC=C1C1=CC=C(S(=O)(=O)NCC2C(NC(=O)N2)=O)C=C1 GEORCJMYOQHATJ-UHFFFAOYSA-N 0.000 description 1
- ISADIWCIVXSRHP-UHFFFAOYSA-N n-[(2,5-dioxoimidazolidin-4-yl)methyl]-4-(4-methylphenoxy)benzenesulfonamide Chemical compound C1=CC(C)=CC=C1OC1=CC=C(S(=O)(=O)NCC2C(NC(=O)N2)=O)C=C1 ISADIWCIVXSRHP-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 239000012134 supernatant fraction Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 208000029257 vision disease Diseases 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0100902A SE0100902D0 (sv) | 2001-03-15 | 2001-03-15 | Compounds |
| PCT/SE2002/000478 WO2002074751A1 (en) | 2001-03-15 | 2002-03-13 | Metalloproteinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004523583A JP2004523583A (ja) | 2004-08-05 |
| JP2004523583A5 true JP2004523583A5 (https=) | 2009-04-30 |
| JP4390457B2 JP4390457B2 (ja) | 2009-12-24 |
Family
ID=20283374
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002573776A Withdrawn JP2004527515A (ja) | 2001-03-15 | 2002-03-13 | メタロプロテイナーゼ阻害剤 |
| JP2002573760A Expired - Fee Related JP4390457B2 (ja) | 2001-03-15 | 2002-03-13 | メタロプロテイナーゼ阻害剤 |
| JP2002573757A Pending JP2004523581A (ja) | 2001-03-15 | 2002-03-13 | メタロプロテイナーゼ阻害剤 |
| JP2009256358A Expired - Fee Related JP5140058B2 (ja) | 2001-03-15 | 2009-11-09 | メタロプロテイナーゼ阻害剤 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002573776A Withdrawn JP2004527515A (ja) | 2001-03-15 | 2002-03-13 | メタロプロテイナーゼ阻害剤 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002573757A Pending JP2004523581A (ja) | 2001-03-15 | 2002-03-13 | メタロプロテイナーゼ阻害剤 |
| JP2009256358A Expired - Fee Related JP5140058B2 (ja) | 2001-03-15 | 2009-11-09 | メタロプロテイナーゼ阻害剤 |
Country Status (32)
| Country | Link |
|---|---|
| US (8) | US7427631B2 (https=) |
| EP (4) | EP1370556B1 (https=) |
| JP (4) | JP2004527515A (https=) |
| KR (4) | KR100886315B1 (https=) |
| CN (5) | CN100526307C (https=) |
| AR (2) | AR035695A1 (https=) |
| AT (3) | ATE493406T1 (https=) |
| AU (2) | AU2002237626B2 (https=) |
| BR (3) | BR0208104A (https=) |
| CA (3) | CA2440630C (https=) |
| CY (1) | CY1107525T1 (https=) |
| CZ (3) | CZ20032499A3 (https=) |
| DE (3) | DE60213216T2 (https=) |
| DK (1) | DK1370556T3 (https=) |
| EE (3) | EE05364B1 (https=) |
| ES (3) | ES2357138T3 (https=) |
| HU (3) | HUP0400194A3 (https=) |
| IL (5) | IL157657A0 (https=) |
| IS (3) | IS6943A (https=) |
| MX (3) | MXPA03008181A (https=) |
| MY (2) | MY136789A (https=) |
| NO (3) | NO326087B1 (https=) |
| NZ (3) | NZ528107A (https=) |
| PL (3) | PL365099A1 (https=) |
| PT (1) | PT1370556E (https=) |
| RU (3) | RU2285695C2 (https=) |
| SE (1) | SE0100902D0 (https=) |
| SI (1) | SI1370556T1 (https=) |
| SK (3) | SK287834B6 (https=) |
| UA (3) | UA77667C2 (https=) |
| WO (3) | WO2002074748A1 (https=) |
| ZA (4) | ZA200306732B (https=) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0100902D0 (sv) | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| SE0100903D0 (sv) * | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| US6890915B2 (en) | 2001-05-25 | 2005-05-10 | Bristol-Myers Squibb Pharma Company | Hydantoins and related heterocycles as inhibitors of matrix metalloproteinases and/or TNF-α converting enzyme (TACE) |
| SE0103710D0 (sv) | 2001-11-07 | 2001-11-07 | Astrazeneca Ab | Compounds |
| DE10221018A1 (de) * | 2002-05-11 | 2003-11-27 | Boehringer Ingelheim Pharma | Verwendung von Hemmern der EGFR-vermittelten Signaltransduktion zur Behandlung von gutartiger Prostatahyperplasie (BPH)/Prostatahypertrophie |
| SE0202539D0 (sv) * | 2002-08-27 | 2002-08-27 | Astrazeneca Ab | Compounds |
| SE0202693D0 (sv) * | 2002-09-11 | 2002-09-11 | Astrazeneca Ab | Compounds |
| GB0221246D0 (en) * | 2002-09-13 | 2002-10-23 | Astrazeneca Ab | Compounds |
| AU2003282920A1 (en) * | 2002-10-04 | 2004-05-04 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or tnf-alpha converting enzyme (tace) |
| JP4866610B2 (ja) | 2003-08-18 | 2012-02-01 | 富士フイルムファインケミカルズ株式会社 | ピリジルテトラヒドロピリジン類およびピリジルピペリジン類 |
| US20050203156A1 (en) * | 2004-03-12 | 2005-09-15 | Wyeth | Hydantoins having RNase modulatory activity |
| US7648992B2 (en) | 2004-07-05 | 2010-01-19 | Astrazeneca Ab | Hydantoin derivatives for the treatment of obstructive airway diseases |
| SE0401762D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Novel compounds |
| SE0401763D0 (sv) * | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Compounds |
| US20080187508A1 (en) * | 2004-09-08 | 2008-08-07 | Boys Town National Research Hospital | Treatment of Golmerular Basement Membrane Disease Involving Matrix Metalloproteinase-12 |
| CA2580762A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
| AR051091A1 (es) | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| CA2580857A1 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| US7829712B2 (en) | 2004-09-20 | 2010-11-09 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-CoA-desaturase |
| AU2005286648A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| EP1807085B1 (en) | 2004-09-20 | 2013-08-21 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| EP2289510A1 (en) * | 2004-09-20 | 2011-03-02 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
| GB0427403D0 (en) * | 2004-12-15 | 2005-01-19 | Astrazeneca Ab | Novel compounds I |
| SE0403086D0 (sv) * | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Compounds |
| SE0403085D0 (sv) * | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
| EP1859356B1 (en) * | 2005-03-16 | 2019-07-10 | Sensus Metering Systems Inc. | Method, system, apparatus, and computer program product for determining a physical location of a sensor |
| AU2006343359A1 (en) | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| US7750012B2 (en) | 2005-12-21 | 2010-07-06 | Decode Genetics Ehf | Biaryl nitrogen-heterocycle inhibitors of LTA4H for treating inflammation |
| AR059036A1 (es) | 2006-01-17 | 2008-03-12 | Schering Corp | Compuestos para el tratamiento de trastornos inflamatorios |
| TW200800954A (en) * | 2006-03-16 | 2008-01-01 | Astrazeneca Ab | Novel crystal modifications |
| TW200740769A (en) * | 2006-03-16 | 2007-11-01 | Astrazeneca Ab | Novel process |
| JP4975807B2 (ja) * | 2006-05-12 | 2012-07-11 | エスセーアー・ハイジーン・プロダクツ・アーベー | 弾性ラミネートおよび弾性ラミネートを製造するための方法 |
| EP2020972B1 (en) * | 2006-05-12 | 2012-11-07 | SCA Hygiene Products AB | A pant-type absorbent article and a method for producing pant-type absorbent articles. |
| WO2008053199A1 (en) * | 2006-10-30 | 2008-05-08 | Astrazeneca Ab | Combination therapy for the treatment of respiratory diseases |
| TW200831488A (en) * | 2006-11-29 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| GB0702456D0 (en) | 2007-02-08 | 2007-03-21 | Astrazeneca Ab | New combination |
| WO2009007747A2 (en) * | 2007-07-11 | 2009-01-15 | Astrazeneca Ab | Hydantoin derivatives used as mmp12 inhibitors |
| EP2211810B1 (en) | 2007-11-14 | 2013-03-13 | Sca Hygiene Products AB | Method of producing an absorbent garment, and an absorbent garment produced according to the method |
| US8303561B2 (en) | 2007-11-14 | 2012-11-06 | Sca Hygiene Products Ab | Method of producing an absorbent garment, and an absorbent garment produced according to the method |
| FR2927330B1 (fr) * | 2008-02-07 | 2010-02-19 | Sanofi Aventis | Derives de 5,6-bisaryl-2-pyridine-carboxamide, leur preparation et leur application en therapeutique comme antagonistes des recepteurs a l'urotensine ii |
| AU2009241365B2 (en) | 2008-04-28 | 2015-01-22 | Revalesio Corporation | Compositions and methods for treating multiple sclerosis |
| FR2944524B1 (fr) | 2009-04-17 | 2012-11-30 | Ipsen Pharma Sas | Derives d'imidazolidine-2,4-dione et leur utilisation comme medicament |
| JP5671453B2 (ja) * | 2009-04-28 | 2015-02-18 | 中外製薬株式会社 | スピロイミダゾロン誘導体 |
| GB0913345D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | New combination 802 |
| WO2011054734A1 (de) * | 2009-11-06 | 2011-05-12 | Basf Se | Eisen- und manganhaltiger heterogenkatalysator und verfahren zur herstellung von olefinen durch umsetzung von kohlenmonoxid mit wasserstoff |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| WO2011073662A1 (en) | 2009-12-17 | 2011-06-23 | Astrazeneca Ab | Combination of a benzoxazinone and a further agent for treating respiratory diseases |
| US20110202284A1 (en) * | 2010-02-10 | 2011-08-18 | Mcreynolds Cristopher | Novel groups of biomarkers for diagnosing alzheimer's disease |
| RU2441068C2 (ru) * | 2010-03-11 | 2012-01-27 | Галина Ивановна Эль-Регистан | Способ направленного изменения активности ферментных белков |
| RU2441069C2 (ru) * | 2010-03-11 | 2012-01-27 | Галина Ивановна Эль-Регистан | Стабилизатор ферментных белков |
| RU2430371C1 (ru) * | 2010-04-26 | 2011-09-27 | Учреждение Российской академии наук Институт ядерной физики им. Г.И. Будкера Сибирского отделения РАН (ИЯФ СО РАН) | Способ дифференциальной диагностики и прогноза миомы и рака эндометрия |
| AU2011261375B2 (en) | 2010-06-04 | 2016-09-22 | Albany Molecular Research, Inc. | Glycine transporter-1 inhibitors, methods of making them, and uses thereof |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| RS61242B1 (sr) * | 2012-09-04 | 2021-01-29 | Shanghai hengrui pharmaceutical co ltd | Derivati imidazolina, postupci njihove pripreme i njihove primene u medicini |
| KR102168738B1 (ko) | 2012-12-10 | 2020-10-22 | 추가이 세이야쿠 가부시키가이샤 | 히단토인 유도체 |
| HUE051782T2 (hu) * | 2013-11-13 | 2021-03-29 | Hankkija Oy | Gyantasavat tartalmazó táplálékkiegészítõ |
| JP6227149B2 (ja) * | 2013-12-31 | 2017-11-08 | イプセン ファルマ ソシエテ パール アクシオン サンプリフィエＩｐｓｅｎ Ｐｈａｒｍａ Ｓ．Ａ．Ｓ． | 新規のイミダゾリジン−２，４−ジオン誘導体 |
| EP2907512A1 (en) | 2014-02-14 | 2015-08-19 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Inhibitors of MMP-12 as antiviral Agents |
| KR102266021B1 (ko) * | 2014-06-09 | 2021-06-16 | 추가이 세이야쿠 가부시키가이샤 | 히단토인 유도체 함유 의약 조성물 |
| KR20200087273A (ko) | 2014-10-24 | 2020-07-20 | 란도스 바이오파마, 인크. | 란티오닌 합성효소 c-유사 2-계 치료제 |
| JO3501B1 (ar) * | 2014-12-22 | 2020-07-05 | Servier Lab | مشتقات 5-{(بيبرازين - 1-يل)-3-أوكسو - بروبيل}- إيميدازوليدين-2، 4 - دايون كمثبطات ل adamts لمعالجة هشاشة العظام) |
| JP6934012B2 (ja) * | 2016-09-23 | 2021-09-08 | 科研製薬株式会社 | （ｒ）‐５‐（３，４‐ジフルオロフェニル）‐５‐［（３‐メチル‐２‐オキソピリジン‐１（２ｈ）‐イル）メチル］イミダゾリジン‐２，４‐ジオンの製造方法およびその製造のための中間体 |
| WO2021011723A1 (en) * | 2019-07-18 | 2021-01-21 | Avidence Therapeutics, Inc. | Anti-osteoarthritis hydantoin compounds and related compositions and methods |
| CA3158234A1 (en) * | 2019-11-14 | 2021-05-20 | Foresee Pharmaceuticals Co., Ltd. | Matrix metalloproteinase (mmp) inhibitors and methods of use thereof |
| BR112022002387A2 (pt) | 2019-12-20 | 2022-09-06 | Landos Biopharma Inc | Composto da fórmula z-y-q-y' ou um sal ou éster farmaceuticamente aceitável do mesmo |
| US12234578B2 (en) | 2020-01-29 | 2025-02-25 | Wisconsin Alumni Research Foundation | Tannin composite fibers |
| US20230255943A1 (en) * | 2020-06-26 | 2023-08-17 | The University Of Birmingham | Mmp-9 and mmp-12 inhibition for treating spinal cord injury or related injury to neurological tissue |
| CN115720578B (zh) * | 2020-07-09 | 2025-06-13 | 深圳信立泰药业股份有限公司 | 并三环类衍生物、其制备方法及其在医药上的应用 |
| CN112574193B (zh) * | 2020-12-31 | 2022-05-17 | 南京医科大学 | 一类口服gsnor抑制剂及其药物用途 |
Family Cites Families (95)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2327890A (en) * | 1940-04-17 | 1943-08-24 | Parke Davis & Co | Substituted phenoxyalkyl ethers |
| US2745875A (en) * | 1953-06-30 | 1956-05-15 | Hoechst Ag | Preparation of nu-acylamino-phenylpropane diols |
| US3452040A (en) | 1966-01-05 | 1969-06-24 | American Home Prod | 5,5-disubstituted hydantoins |
| US3529019A (en) * | 1968-04-23 | 1970-09-15 | Colgate Palmolive Co | Alkylaryloxy alanines |
| CS152617B1 (https=) | 1970-12-29 | 1974-02-22 | ||
| CS151744B1 (https=) * | 1971-01-19 | 1973-11-19 | ||
| US3849574A (en) * | 1971-05-24 | 1974-11-19 | Colgate Palmolive Co | Alpha-substituted-beta-arylthioalkyl amino-acids,for increasing heart rate |
| US4315031A (en) * | 1977-09-01 | 1982-02-09 | Science Union Et Cie | Thiosubstituted amino acids |
| GB1601310A (en) | 1978-05-23 | 1981-10-28 | Lilly Industries Ltd | Aryl hydantoins |
| JPS6172762A (ja) | 1984-09-17 | 1986-04-14 | Kanegafuchi Chem Ind Co Ltd | 光学活性ヒダントイン類の製造法 |
| JPS61212292A (ja) * | 1985-03-19 | 1986-09-20 | Mitsui Toatsu Chem Inc | Ｄ−α−アミノ酸の製造方法 |
| CA1325222C (en) | 1985-08-23 | 1993-12-14 | Lederle (Japan), Ltd. | Process for producing 4-biphenylylacetic acid |
| GB8618559D0 (en) | 1986-07-30 | 1986-09-10 | Genetics Int Inc | Rhodococcus bacterium |
| JPH0279879A (ja) | 1988-09-17 | 1990-03-20 | Canon Inc | 画像形成装置 |
| US4983771A (en) | 1989-09-18 | 1991-01-08 | Hexcel Corporation | Method for resolution of D,L-alpha-phenethylamine with D(-)mandelic acid |
| NL9000386A (nl) | 1990-02-16 | 1991-09-16 | Stamicarbon | Werkwijze voor de bereiding van optisch aktief aminozuuramide. |
| DK161690D0 (da) | 1990-07-05 | 1990-07-05 | Novo Nordisk As | Fremgangsmaade til fremstilling af enantiomere forbindelser |
| IL99957A0 (en) | 1990-11-13 | 1992-08-18 | Merck & Co Inc | Piperidinylcamphorsulfonyl oxytocin antagonists and pharmaceutical compositions containing them |
| PH31245A (en) * | 1991-10-30 | 1998-06-18 | Janssen Pharmaceutica Nv | 1,3-Dihydro-2H-imidazoÄ4,5-BÜ-quinolin-2-one derivatives. |
| US5308853A (en) * | 1991-12-20 | 1994-05-03 | Warner-Lambert Company | Substituted-5-methylidene hydantoins with AT1 receptor antagonist properties |
| US5246943A (en) | 1992-05-19 | 1993-09-21 | Warner-Lambert Company | Substituted 1,2,3,4-tetahydroisoquinolines with angiotensin II receptor antagonist properties |
| NL9201230A (nl) | 1992-07-09 | 1994-02-01 | Dsm Nv | Werkwijze voor de bereiding van optisch aktief methionineamide. |
| EP0640594A1 (en) | 1993-08-23 | 1995-03-01 | Fujirebio Inc. | Hydantoin derivative as metalloprotease inhibitor |
| JPH07105549A (ja) | 1993-09-30 | 1995-04-21 | Canon Inc | 光学的情報記録再生方法及び光学的情報記録再生装置 |
| AU687953B2 (en) | 1993-11-16 | 1998-03-05 | Merck & Co., Inc. | Piperidinylcamphorsulfonyl oxytocin antagonists |
| CN1048247C (zh) | 1994-01-31 | 2000-01-12 | 美国辉瑞有限公司 | 神经保护的苯并二氢吡喃化合物 |
| EP0709375B1 (en) | 1994-10-25 | 2005-05-18 | AstraZeneca AB | Therapeutic heterocycles |
| ZA96211B (en) | 1995-01-12 | 1996-07-26 | Teva Pharma | Compositions containing and methods of using 1- aminoindan and derivatives thereof and process for preparing optically active 1-aminoindan derivatives |
| US5863949A (en) | 1995-03-08 | 1999-01-26 | Pfizer Inc | Arylsulfonylamino hydroxamic acid derivatives |
| US6166041A (en) * | 1995-10-11 | 2000-12-26 | Euro-Celtique, S.A. | 2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma |
| DE19540027A1 (de) * | 1995-10-27 | 1997-04-30 | Gruenenthal Gmbh | Substituierte Imidazolidin-2,4-dion-Verbindungen als pharmazeutische Wirkstoffe |
| WO1997019075A1 (en) * | 1995-11-22 | 1997-05-29 | Darwin Discovery Limited | Mercaptoalkylpeptidyl compounds having an imidazole substituent and their use as inhibitors of matrix metalloproteinases (mmp) and/or tumour necrosis factor (tnf) |
| GB9616643D0 (en) * | 1996-08-08 | 1996-09-25 | Chiroscience Ltd | Compounds |
| US5919790A (en) * | 1996-10-11 | 1999-07-06 | Warner-Lambert Company | Hydroxamate inhibitors of interleukin-1β converting enzyme |
| ATE212619T1 (de) | 1996-10-22 | 2002-02-15 | Upjohn Co | Alpha-amino sulfonyl hydroxamsäure als matrix metalloproteinase inhibitoren |
| IL132170A0 (en) * | 1997-05-06 | 2001-03-19 | Novo Nordisk As | Novel heterocyclic compounds |
| DE59802394D1 (de) | 1997-05-09 | 2002-01-24 | Hoechst Ag | Substituierte Diaminocarbonsäuren |
| TR199903148T2 (xx) | 1997-06-21 | 2000-04-21 | Roche Diagnostics Gmbh | Antimetastatik ve antit�m�r etkinli�i olan barbit�rik asit t�revleri. |
| DE19726427A1 (de) | 1997-06-23 | 1998-12-24 | Boehringer Mannheim Gmbh | Pyrimidin-2,4,6-trion-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| NZ501166A (en) * | 1997-07-31 | 2001-12-21 | Abbott Lab | Reverse hydroxamate-containing compounds and their use as inhibitors of matrix metalloproteinases |
| TW514634B (en) | 1997-10-14 | 2002-12-21 | Lilly Co Eli | Process to make chiral compounds |
| DE69811111T2 (de) * | 1997-11-12 | 2003-07-24 | Darwin Discovery Ltd., Cambridge | Hydroxamsäure- und carbonsäurederivate mit mmp und tnf hemmender wirkung |
| RU2208609C2 (ru) | 1998-02-04 | 2003-07-20 | Новартис Аг | Сульфониламинопроизводные, которые ингибируют разлагающие матрикс металлопротеиназы |
| US6329418B1 (en) * | 1998-04-14 | 2001-12-11 | The Procter & Gamble Company | Substituted pyrrolidine hydroxamate metalloprotease inhibitors |
| EP1077974A1 (en) | 1998-05-14 | 2001-02-28 | Du Pont Pharmaceuticals Company | Substituted aryl hydroxamic acids as metalloproteinase inhibitors |
| CN1295561A (zh) | 1998-06-03 | 2001-05-16 | Gpinil控股公司 | N－杂环羧酸或羧酸等排物的n－结合氨磺酰 |
| AU4692399A (en) | 1998-06-17 | 2000-01-05 | Du Pont Pharmaceuticals Company | Cyclic hydroxamic acids as metalloproteinase inhibitors |
| FR2782082B3 (fr) | 1998-08-05 | 2000-09-22 | Sanofi Sa | Formes cristallines de (r)-(+)-n-[[3-[1-benzoyl-3-(3,4- dichlorophenyl)piperidin-3-yl]prop-1-yl]-4-phenylpiperidin-4 -yl]-n-methylacetamide (osanetant) et procede pour la preparation dudit compose |
| US6339101B1 (en) | 1998-08-14 | 2002-01-15 | Gpi Nil Holdings, Inc. | N-linked sulfonamides of N-heterocyclic carboxylic acids or isosteres for vision and memory disorders |
| JP2000127349A (ja) * | 1998-08-21 | 2000-05-09 | Komori Corp | 凹版印刷機 |
| EP1107953A1 (en) | 1998-08-29 | 2001-06-20 | British Biotech Pharmaceuticals Limited | Hydroxamic acid derivatives as proteinase inhibitors |
| GB9919776D0 (en) | 1998-08-31 | 1999-10-27 | Zeneca Ltd | Compoujnds |
| EP1117616B1 (en) | 1998-10-07 | 2003-04-23 | Yazaki Corporation | Sol-gel process using porous mold |
| DK1004578T3 (da) * | 1998-11-05 | 2004-06-28 | Pfizer Prod Inc | 5-oxo-pyrrolidin-2-carboxylsyrehydroxamidderivater |
| WO2000035886A2 (en) | 1998-12-18 | 2000-06-22 | Axys Pharmaceuticals, Inc. | (hetero)aryl-bicyclic heteroaryl derivatives, their preparation and their use as protease inhibitors |
| EP1150975A1 (en) * | 1998-12-31 | 2001-11-07 | Aventis Pharmaceuticals Inc. | 1-carboxymethyl-2-oxo-azepan derivatives useful as selective inhibitors of mmp-12 |
| US6340691B1 (en) * | 1999-01-27 | 2002-01-22 | American Cyanamid Company | Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and tace inhibitors |
| KR100440643B1 (ko) | 1999-01-28 | 2004-07-21 | 쥬가이 세이야쿠 가부시키가이샤 | 치환 페네틸아민 유도체 |
| US6294694B1 (en) | 1999-06-04 | 2001-09-25 | Wisconsin Alumni Research Foundation | Matrix metalloproteinase inhibitors and method of using same |
| GB9916562D0 (en) * | 1999-07-14 | 1999-09-15 | Pharmacia & Upjohn Spa | 3-Arylsulfonyl-2-(substituted-methyl) propanoic acid derivatives as matrix metalloproteinase inhibitora |
| US20020006920A1 (en) * | 1999-07-22 | 2002-01-17 | Robinson Ralph Pelton | Arylsulfonylamino hydroxamic acid derivatives |
| US6266453B1 (en) | 1999-07-26 | 2001-07-24 | Computerized Medical Systems, Inc. | Automated image fusion/alignment system and method |
| EP1078923B1 (en) | 1999-08-02 | 2006-03-08 | F. Hoffmann-La Roche Ag | Process for the preparation of benzothiophene derivatives |
| KR20020060160A (ko) | 1999-08-12 | 2002-07-16 | 파마시아 이탈리아 에스.피.에이. | 3(5)-아미노-피라졸 유도체, 이의 제조 방법 및항종양제로서의 이의 용도 |
| JP3710964B2 (ja) | 1999-08-26 | 2005-10-26 | 富士通株式会社 | ディスプレイデバイスのレイアウト設計方法 |
| SE9904044D0 (sv) | 1999-11-09 | 1999-11-09 | Astra Ab | Compounds |
| US6525202B2 (en) | 2000-07-17 | 2003-02-25 | Wyeth | Cyclic amine phenyl beta-3 adrenergic receptor agonists |
| JP5046466B2 (ja) | 2000-08-11 | 2012-10-10 | 科研製薬株式会社 | ２，３−ジフェニルプロピオン酸誘導体またはその塩、それを用いた医薬および細胞接着阻害剤ならびにその使用方法 |
| US20020065219A1 (en) | 2000-08-15 | 2002-05-30 | Naidu B. Narasimhulu | Water soluble thiazolyl peptide derivatives |
| US20020091107A1 (en) | 2000-09-08 | 2002-07-11 | Madar David J. | Oxazolidinone antibacterial agents |
| WO2002020515A1 (en) | 2000-09-08 | 2002-03-14 | Abbott Laboratories | Oxazolidinone antibacterial agents |
| EP1191024A1 (en) | 2000-09-22 | 2002-03-27 | Harald Tschesche | Thiadiazines and their use as inhibitors of metalloproteinases |
| SE0100903D0 (sv) | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| JP2004527511A (ja) | 2001-03-15 | 2004-09-09 | アストラゼネカ・アクチエボラーグ | メタロプロテイナーゼ阻害剤 |
| SE0100902D0 (sv) | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| US6890915B2 (en) | 2001-05-25 | 2005-05-10 | Bristol-Myers Squibb Pharma Company | Hydantoins and related heterocycles as inhibitors of matrix metalloproteinases and/or TNF-α converting enzyme (TACE) |
| GB0114004D0 (en) | 2001-06-08 | 2001-08-01 | Glaxo Group Ltd | Chemical compounds |
| SE0103710D0 (sv) | 2001-11-07 | 2001-11-07 | Astrazeneca Ab | Compounds |
| JP4485941B2 (ja) | 2002-06-05 | 2010-06-23 | 株式会社カネカ | 光学活性α−メチルシステイン誘導体の製造方法 |
| SE0202539D0 (sv) | 2002-08-27 | 2002-08-27 | Astrazeneca Ab | Compounds |
| SE0202693D0 (sv) | 2002-09-11 | 2002-09-11 | Astrazeneca Ab | Compounds |
| SE0202692D0 (sv) | 2002-09-11 | 2002-09-11 | Astrazeneca Ab | Compounds |
| GB0221246D0 (en) | 2002-09-13 | 2002-10-23 | Astrazeneca Ab | Compounds |
| GB0221250D0 (en) | 2002-09-13 | 2002-10-23 | Astrazeneca Ab | Compounds |
| US6890913B2 (en) * | 2003-02-26 | 2005-05-10 | Food Industry Research And Development Institute | Chitosans |
| US20040266832A1 (en) | 2003-06-26 | 2004-12-30 | Li Zheng J. | Crystal forms of 2-(3-difluoromethyl-5-phenyl-pyrazol-1-yl)-5-methanesulfonyl pyridine |
| TWI220073B (en) | 2003-07-24 | 2004-08-01 | Au Optronics Corp | Method for manufacturing polysilicon film |
| US7648992B2 (en) | 2004-07-05 | 2010-01-19 | Astrazeneca Ab | Hydantoin derivatives for the treatment of obstructive airway diseases |
| SE0401762D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Novel compounds |
| SE0401763D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Compounds |
| SE0403086D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Compounds |
| SE0403085D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
| TW200800954A (en) | 2006-03-16 | 2008-01-01 | Astrazeneca Ab | Novel crystal modifications |
| TW200740769A (en) | 2006-03-16 | 2007-11-01 | Astrazeneca Ab | Novel process |
| TW200831488A (en) | 2006-11-29 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
-
2001
- 2001-03-15 SE SE0100902A patent/SE0100902D0/xx unknown
-
2002
- 2002-03-13 AT AT06008158T patent/ATE493406T1/de not_active IP Right Cessation
- 2002-03-13 UA UA2003098170A patent/UA77667C2/uk unknown
- 2002-03-13 JP JP2002573776A patent/JP2004527515A/ja not_active Withdrawn
- 2002-03-13 PL PL02365099A patent/PL365099A1/xx unknown
- 2002-03-13 CN CNB02809915XA patent/CN100526307C/zh not_active Expired - Fee Related
- 2002-03-13 SK SK1092-2003A patent/SK287834B6/sk not_active IP Right Cessation
- 2002-03-13 NZ NZ528107A patent/NZ528107A/en unknown
- 2002-03-13 MX MXPA03008181A patent/MXPA03008181A/es unknown
- 2002-03-13 IL IL15765702A patent/IL157657A0/xx unknown
- 2002-03-13 KR KR1020037011987A patent/KR100886315B1/ko not_active Expired - Fee Related
- 2002-03-13 MX MXPA03008177A patent/MXPA03008177A/es active IP Right Grant
- 2002-03-13 SI SI200230386T patent/SI1370556T1/sl unknown
- 2002-03-13 EE EEP200300451A patent/EE05364B1/xx not_active IP Right Cessation
- 2002-03-13 DE DE60213216T patent/DE60213216T2/de not_active Expired - Lifetime
- 2002-03-13 SK SK1095-2003A patent/SK10952003A3/sk not_active Application Discontinuation
- 2002-03-13 UA UA2003098171A patent/UA78502C2/uk unknown
- 2002-03-13 WO PCT/SE2002/000473 patent/WO2002074748A1/en not_active Ceased
- 2002-03-13 DK DK02704031T patent/DK1370556T3/da active
- 2002-03-13 PL PL364706A patent/PL205315B1/pl not_active IP Right Cessation
- 2002-03-13 NZ NZ528140A patent/NZ528140A/en not_active IP Right Cessation
- 2002-03-13 CA CA2440630A patent/CA2440630C/en not_active Expired - Fee Related
- 2002-03-13 JP JP2002573760A patent/JP4390457B2/ja not_active Expired - Fee Related
- 2002-03-13 EE EEP200300445A patent/EE05431B1/xx not_active IP Right Cessation
- 2002-03-13 PT PT02704031T patent/PT1370556E/pt unknown
- 2002-03-13 CZ CZ20032499A patent/CZ20032499A3/cs unknown
- 2002-03-13 SK SK1096-2003A patent/SK287766B6/sk not_active IP Right Cessation
- 2002-03-13 EP EP02704031A patent/EP1370556B1/en not_active Expired - Lifetime
- 2002-03-13 US US10/471,900 patent/US7427631B2/en not_active Expired - Fee Related
- 2002-03-13 EP EP02704032A patent/EP1370534A1/en not_active Withdrawn
- 2002-03-13 WO PCT/SE2002/000478 patent/WO2002074751A1/en not_active Ceased
- 2002-03-13 DE DE60238794T patent/DE60238794D1/de not_active Expired - Lifetime
- 2002-03-13 CN CNA200910147512XA patent/CN101602731A/zh active Pending
- 2002-03-13 RU RU2003127733/04A patent/RU2285695C2/ru not_active IP Right Cessation
- 2002-03-13 HU HU0400194A patent/HUP0400194A3/hu unknown
- 2002-03-13 BR BR0208104-0A patent/BR0208104A/pt not_active IP Right Cessation
- 2002-03-13 BR BR0207983-6A patent/BR0207983A/pt not_active IP Right Cessation
- 2002-03-13 CN CNB028097882A patent/CN1304377C/zh not_active Expired - Fee Related
- 2002-03-13 IL IL15765202A patent/IL157652A0/xx unknown
- 2002-03-13 ES ES06008158T patent/ES2357138T3/es not_active Expired - Lifetime
- 2002-03-13 JP JP2002573757A patent/JP2004523581A/ja active Pending
- 2002-03-13 KR KR10-2003-7011982A patent/KR20030082987A/ko not_active Withdrawn
- 2002-03-13 ES ES02704037T patent/ES2352246T3/es not_active Expired - Lifetime
- 2002-03-13 CZ CZ20032497A patent/CZ20032497A3/cs unknown
- 2002-03-13 CA CA2440473A patent/CA2440473C/en not_active Expired - Fee Related
- 2002-03-13 AT AT02704037T patent/ATE484496T1/de not_active IP Right Cessation
- 2002-03-13 EE EEP200300449A patent/EE200300449A/xx unknown
- 2002-03-13 AU AU2002237626A patent/AU2002237626B2/en not_active Ceased
- 2002-03-13 HU HU0400202A patent/HUP0400202A3/hu unknown
- 2002-03-13 AU AU2002237632A patent/AU2002237632B2/en not_active Ceased
- 2002-03-13 CZ CZ20032500A patent/CZ20032500A3/cs unknown
- 2002-03-13 EP EP06008158A patent/EP1676846B1/en not_active Expired - Lifetime
- 2002-03-13 EP EP02704037A patent/EP1370537B1/en not_active Expired - Lifetime
- 2002-03-13 MY MYPI20020910A patent/MY136789A/en unknown
- 2002-03-13 RU RU2003127734/04A patent/RU2288228C2/ru not_active IP Right Cessation
- 2002-03-13 CN CNB02810093XA patent/CN1269804C/zh not_active Expired - Fee Related
- 2002-03-13 KR KR1020087017665A patent/KR100879905B1/ko not_active Expired - Fee Related
- 2002-03-13 UA UA2003098168A patent/UA77408C2/uk unknown
- 2002-03-13 MY MYPI20020904A patent/MY136141A/en unknown
- 2002-03-13 US US10/471,810 patent/US7368465B2/en not_active Expired - Fee Related
- 2002-03-13 KR KR10-2003-7011981A patent/KR20030082986A/ko not_active Withdrawn
- 2002-03-13 US US10/471,500 patent/US20040106659A1/en not_active Abandoned
- 2002-03-13 PL PL02364707A patent/PL364707A1/xx not_active Application Discontinuation
- 2002-03-13 WO PCT/SE2002/000472 patent/WO2002074767A1/en not_active Ceased
- 2002-03-13 CA CA002440631A patent/CA2440631A1/en not_active Abandoned
- 2002-03-13 RU RU2003127735/04A patent/RU2293729C2/ru not_active IP Right Cessation
- 2002-03-13 CN CN2006101061525A patent/CN1962641B/zh not_active Expired - Fee Related
- 2002-03-13 MX MXPA03008191A patent/MXPA03008191A/es active IP Right Grant
- 2002-03-13 AT AT02704031T patent/ATE333454T1/de active
- 2002-03-13 DE DE60237965T patent/DE60237965D1/de not_active Expired - Lifetime
- 2002-03-13 NZ NZ528106A patent/NZ528106A/en not_active IP Right Cessation
- 2002-03-13 HU HU0400327A patent/HUP0400327A3/hu unknown
- 2002-03-13 ES ES02704031T patent/ES2267986T3/es not_active Expired - Lifetime
- 2002-03-13 IL IL15765602A patent/IL157656A0/xx unknown
- 2002-03-13 BR BR0207984-4A patent/BR0207984A/pt not_active IP Right Cessation
- 2002-03-15 AR ARP020100943A patent/AR035695A1/es unknown
- 2002-03-15 AR ARP020100944A patent/AR035443A1/es active IP Right Grant
-
2003
- 2003-08-28 IL IL157652A patent/IL157652A/en not_active IP Right Cessation
- 2003-08-28 ZA ZA200306732A patent/ZA200306732B/en unknown
- 2003-08-28 ZA ZA200306734A patent/ZA200306734B/en unknown
- 2003-08-28 IL IL157656A patent/IL157656A/en not_active IP Right Cessation
- 2003-08-28 ZA ZA200306731A patent/ZA200306731B/en unknown
- 2003-08-28 ZA ZA200306737A patent/ZA200306737B/en unknown
- 2003-09-09 IS IS6943A patent/IS6943A/is unknown
- 2003-09-09 IS IS6942A patent/IS6942A/is unknown
- 2003-09-10 IS IS6946A patent/IS6946A/is unknown
- 2003-09-12 NO NO20034042A patent/NO326087B1/no not_active IP Right Cessation
- 2003-09-12 NO NO20034044A patent/NO20034044L/no unknown
- 2003-09-12 NO NO20034045A patent/NO327114B1/no not_active IP Right Cessation
-
2006
- 2006-10-13 CY CY20061101477T patent/CY1107525T1/el unknown
-
2007
- 2007-10-30 US US11/928,040 patent/US7625934B2/en not_active Expired - Fee Related
-
2008
- 2008-05-05 US US12/114,901 patent/US7666892B2/en not_active Expired - Fee Related
- 2008-05-06 US US12/115,785 patent/US7754750B2/en not_active Expired - Fee Related
-
2009
- 2009-11-09 JP JP2009256358A patent/JP5140058B2/ja not_active Expired - Fee Related
-
2010
- 2010-01-26 US US12/693,852 patent/US8153673B2/en not_active Expired - Fee Related
- 2010-07-06 US US12/830,763 patent/US20110003853A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2004523583A5 (https=) | ||
| JP4589529B2 (ja) | Ｘａ因子阻害剤としてのインドール誘導体 | |
| EP3490989B1 (en) | Covalent inhibitors of pad4 | |
| KR101907573B1 (ko) | 비대칭적 유레아 및 그 의학적 용도 | |
| EP1397137B1 (en) | Hydantion derivatives as inhibitors of matrix metalloproteinases | |
| PT889876E (pt) | Derivados de fenilenossulfonamidas meta-substituidas | |
| JPH03133964A (ja) | ピリミジン誘導体 | |
| JP2010077137A (ja) | メタロプロテイナーゼ阻害剤 | |
| WO2001036376A1 (en) | Novel phenylalanine derivatives | |
| EA005578B1 (ru) | Ингибиторы клеточной адгезии | |
| JP2006510672A (ja) | プラスミノーゲン活性化因子の阻害因子−１（ｐａｉ−１）の阻害剤としての置換インドールオキソ−アセチルアミノ酢酸誘導体 | |
| CA2211890A1 (en) | Fibrinogen receptor antagonists | |
| AU2005279088A1 (en) | Sulphonamide derivatives, their preparation and their therapeutic application | |
| TW200303861A (en) | Heteroaryl nitriles | |
| CA2754934A1 (en) | Substituted 3-aminoisoxazolopyridines as kcnq2/3 modulators | |
| CA2168345A1 (en) | Phenylamidine derivatives as platelet aggregation inhibitors | |
| AU781837B2 (en) | 3-azabicyclo (3.1.0) hexane derivatives having opioid receptor affinity | |
| WO2020210831A1 (en) | Inhibitors of cd40-cd154 binding | |
| WO2004060376A1 (en) | The r-isomer of beta amino acid compounds as integrin receptor antagonists derivatives | |
| EP0649843B1 (en) | Thiazoline derivative | |
| CN110437220B (zh) | 三氮唑类化合物及其应用 | |
| EP1103543A1 (en) | Novel urea derivatives bearing nitrogenous aromatic heterocycles | |
| JPWO1994002472A1 (ja) | チアゾリン誘導体 | |
| SK5712003A3 (en) | Novel aminotriazolone compounds, method for preparing same and pharmaceutical compositions containing same | |
| US5478945A (en) | Thiazoline derivatives |