SK282134B6 - Derivát oxazolidinónu, spôsob jeho prípravy, farmaceutický prostriedok s jeho obsahom a použitie - Google Patents
Derivát oxazolidinónu, spôsob jeho prípravy, farmaceutický prostriedok s jeho obsahom a použitie Download PDFInfo
- Publication number
- SK282134B6 SK282134B6 SK1121-94A SK112194A SK282134B6 SK 282134 B6 SK282134 B6 SK 282134B6 SK 112194 A SK112194 A SK 112194A SK 282134 B6 SK282134 B6 SK 282134B6
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- oxazolidin
- group
- bis
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 7
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical class C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 title description 2
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 6
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 5
- 206010003210 Arteriosclerosis Diseases 0.000 claims abstract description 4
- 206010008190 Cerebrovascular accident Diseases 0.000 claims abstract description 4
- 206010061218 Inflammation Diseases 0.000 claims abstract description 4
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 4
- 208000006011 Stroke Diseases 0.000 claims abstract description 4
- 208000011775 arteriosclerosis disease Diseases 0.000 claims abstract description 4
- 230000004054 inflammatory process Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 6
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000003797 solvolysis reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 102100025306 Integrin alpha-IIb Human genes 0.000 claims description 3
- 101710149643 Integrin alpha-IIb Proteins 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000005557 antagonist Substances 0.000 claims description 2
- BMOALWFKHPNNEY-UHFFFAOYSA-N methyl 2-[4-[[3-(4-carbamimidoylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methoxy]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1OCC1OC(=O)N(C=2C=CC(=CC=2)C(N)=N)C1 BMOALWFKHPNNEY-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 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 abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 229910052708 sodium Inorganic materials 0.000 abstract description 4
- 102000008946 Fibrinogen Human genes 0.000 abstract description 3
- 108010049003 Fibrinogen Proteins 0.000 abstract description 3
- 229940012952 fibrinogen Drugs 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 229910052700 potassium Inorganic materials 0.000 abstract description 3
- 229910052744 lithium Inorganic materials 0.000 abstract description 2
- 206010061216 Infarction Diseases 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 230000000747 cardiac effect Effects 0.000 abstract 1
- 230000007574 infarction Effects 0.000 abstract 1
- -1 1-methylpentyl Chemical group 0.000 description 70
- 238000006243 chemical reaction Methods 0.000 description 26
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 125000006239 protecting group Chemical group 0.000 description 12
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
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- 239000002904 solvent Substances 0.000 description 9
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
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- 239000002585 base Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
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- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 3
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- 239000012154 double-distilled water Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- RJJARNBMLSDETN-UHFFFAOYSA-N methyl 2-[4-[[3-(4-cyanophenyl)-2-oxo-1,3-oxazolidin-5-yl]methoxy]phenyl]acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1OCC1OC(=O)N(C=2C=CC(=CC=2)C#N)C1 RJJARNBMLSDETN-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
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- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
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- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- IFDVVDMDQQMPEB-UHFFFAOYSA-N methyl 2-[2-[[3-(4-cyanophenyl)-2-oxo-1,3-oxazolidin-5-yl]methoxy]phenyl]acetate Chemical compound COC(=O)CC1=CC=CC=C1OCC1OC(=O)N(C=2C=CC(=CC=2)C#N)C1 IFDVVDMDQQMPEB-UHFFFAOYSA-N 0.000 description 2
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- UZYQSNQJLWTICD-UHFFFAOYSA-N 2-(n-benzoylanilino)-2,2-dinitroacetic acid Chemical compound C=1C=CC=CC=1N(C(C(=O)O)([N+]([O-])=O)[N+]([O-])=O)C(=O)C1=CC=CC=C1 UZYQSNQJLWTICD-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- DZNCSTUKVMBRTF-UHFFFAOYSA-N 2-[2-[[3-(4-carbamimidoylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methoxy]phenyl]acetic acid Chemical compound C1=CC(C(=N)N)=CC=C1N1C(=O)OC(COC=2C(=CC=CC=2)CC(O)=O)C1 DZNCSTUKVMBRTF-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- JGKIXQVVHVHVHG-UHFFFAOYSA-M sodium;4-(2-methoxy-2-oxoethyl)phenolate Chemical compound [Na+].COC(=O)CC1=CC=C([O-])C=C1 JGKIXQVVHVHVHG-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/04—Amoebicides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4332384A DE4332384A1 (de) | 1993-09-23 | 1993-09-23 | Adhäsionsrezeptor-Antagonisten III |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK112194A3 SK112194A3 (en) | 1995-05-10 |
| SK282134B6 true SK282134B6 (sk) | 2001-11-06 |
Family
ID=6498425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1121-94A SK282134B6 (sk) | 1993-09-23 | 1994-09-19 | Derivát oxazolidinónu, spôsob jeho prípravy, farmaceutický prostriedok s jeho obsahom a použitie |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US5561148A (cs) |
| EP (1) | EP0645376B1 (cs) |
| JP (1) | JPH07179441A (cs) |
| KR (1) | KR100347849B1 (cs) |
| CN (1) | CN1052227C (cs) |
| AT (1) | ATE178599T1 (cs) |
| AU (1) | AU682050B2 (cs) |
| CA (1) | CA2132579A1 (cs) |
| CZ (1) | CZ288819B6 (cs) |
| DE (2) | DE4332384A1 (cs) |
| DK (1) | DK0645376T3 (cs) |
| ES (1) | ES2132295T3 (cs) |
| GR (1) | GR3030512T3 (cs) |
| HU (1) | HU217980B (cs) |
| NO (1) | NO305203B1 (cs) |
| PL (1) | PL180462B1 (cs) |
| RU (1) | RU2125560C1 (cs) |
| SK (1) | SK282134B6 (cs) |
| TW (1) | TW381086B (cs) |
| UA (1) | UA40590C2 (cs) |
| ZA (1) | ZA947405B (cs) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4313411A1 (de) * | 1993-04-23 | 1994-10-27 | Basf Ag | 3-Halogen-3-hetarylcarbonsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung |
| DE4332384A1 (de) * | 1993-09-23 | 1995-03-30 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten III |
| DE4429461A1 (de) * | 1994-08-19 | 1996-02-22 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
| ES2123889T3 (es) * | 1994-11-02 | 1999-01-16 | Merck Patent Gmbh | Antagonistas de receptores de adhesion. |
| DE4439846A1 (de) * | 1994-11-08 | 1996-05-09 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
| CZ231497A3 (cs) * | 1995-02-03 | 1998-08-12 | Pharmacia & Upjohn Company | Antimikrobiální fenyloxazolidinony substituované heteroaromatickým kruhem |
| DE19516483A1 (de) * | 1995-05-05 | 1996-11-07 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
| DE19524765A1 (de) * | 1995-07-07 | 1997-01-09 | Boehringer Mannheim Gmbh | Neue Oxazolidinonderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE19601265A1 (de) * | 1996-01-16 | 1997-07-17 | Bayer Ag | 2-Oxo- und 2-Thio-1,2-dihydrochinolinyl-oxazolidinone |
| DE19601264A1 (de) * | 1996-01-16 | 1997-07-17 | Bayer Ag | Pyrido-annellierte Thienyl- und Furanyl-Oxazolidinone |
| DE19601627A1 (de) * | 1996-01-18 | 1997-07-24 | Bayer Ag | Heteroatomhaltige Cyclopentanopyridyl-Oxazolidinone |
| HRP970049A2 (en) | 1996-02-06 | 1998-04-30 | Bayer Ag | New heteroaryl oxazolidinones |
| DE19604223A1 (de) | 1996-02-06 | 1997-08-07 | Bayer Ag | Neue substituierte Oxazolidinone |
| SK8199A3 (en) * | 1996-07-25 | 2000-04-10 | Biogen Inc | Cell adhesion inhibitors, preparation method thereof and pharmaceutical composition with their content |
| AU729488B2 (en) * | 1996-08-29 | 2001-02-01 | Merck & Co., Inc. | Compositions and methods for administering integrin receptor antagonists |
| GB9812019D0 (en) * | 1998-06-05 | 1998-07-29 | Zeneca Ltd | Chemical compounds |
| NZ508174A (en) * | 1998-06-05 | 2003-10-31 | Astrazeneca Ab | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
| JP2002533422A (ja) | 1998-12-23 | 2002-10-08 | ジー・ディー・サール・アンド・カンパニー | 新形成の治療における併用療法としてシクロオキシゲナーゼ−２阻害剤とインテグリン拮抗剤を使用する方法 |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| DE19962924A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| DE10129725A1 (de) | 2001-06-20 | 2003-01-02 | Bayer Ag | Kombinationstherapie substituierter Oxazolidinone |
| DE10159453A1 (de) * | 2001-12-04 | 2003-06-18 | Merck Patent Gmbh | Verwendung von 1-Phenyl-oxazolidin-2-on-Verbindungen als Protease |
| US7141588B2 (en) * | 2002-02-25 | 2006-11-28 | Pfizer, Inc. | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| WO2003072576A2 (en) * | 2002-02-28 | 2003-09-04 | Astrazeneca Ab | Oxazolidinone derivatives, processes for their preparation, and pharmaceutical compositions containing them |
| DE10300111A1 (de) | 2003-01-07 | 2004-07-15 | Bayer Healthcare Ag | Verfahren zur Herstellung von 5-Chlor-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophencarboxamid |
| DE10355461A1 (de) | 2003-11-27 | 2005-06-23 | Bayer Healthcare Ag | Verfahren zur Herstellung einer festen, oral applizierbaren pharmazeutischen Zusammensetzung |
| UA87854C2 (en) | 2004-06-07 | 2009-08-25 | Мерк Энд Ко., Инк. | N-(2-benzyl)-2-phenylbutanamides as androgen receptor modulators |
| SG156618A1 (en) | 2004-09-07 | 2009-11-26 | Archemix Corp | Aptamers to von willebrand factor and their use as thrombotic disease therapeutics |
| US7566701B2 (en) * | 2004-09-07 | 2009-07-28 | Archemix Corp. | Aptamers to von Willebrand Factor and their use as thrombotic disease therapeutics |
| EP1791557A4 (en) * | 2004-09-07 | 2009-09-23 | Archemix Corp | MEDICAL CHEMISTRY USING APTAMERS |
| DE102004062475A1 (de) * | 2004-12-24 | 2006-07-06 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit modifizierter Freisetzung |
| EP1685841A1 (en) | 2005-01-31 | 2006-08-02 | Bayer Health Care Aktiengesellschaft | Prevention and treatment of thromboembolic disorders |
| DE102005045518A1 (de) | 2005-09-23 | 2007-03-29 | Bayer Healthcare Ag | 2-Aminoethoxyessigsäure-Derivate und ihre Verwendung |
| DE102005047558A1 (de) * | 2005-10-04 | 2008-02-07 | Bayer Healthcare Ag | Kombinationstherapie substituierter Oxazolidinone zur Prophylaxe und Behandlung von cerebralen Durchblutungsstörungen |
| US8188270B2 (en) | 2005-10-04 | 2012-05-29 | Bayer Schering Pharma Aktiengesellschaft | Polymorphous form of 5-chloro-N-({(5S)-2-oxo-3[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidine-5-yl}-methyl)-2-thiophene carboxamide |
| DE102005047561A1 (de) | 2005-10-04 | 2007-04-05 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit schneller Wirkstofffreisetzung |
| DE102006051625A1 (de) * | 2006-11-02 | 2008-05-08 | Bayer Materialscience Ag | Kombinationstherapie substituierter Oxazolidinone |
| US20090203766A1 (en) * | 2007-06-01 | 2009-08-13 | Archemix Corp. | vWF aptamer formulations and methods for use |
| PL2222636T3 (pl) | 2007-12-21 | 2014-04-30 | Ligand Pharm Inc | Selektywne modulatory receptorów androgenowych (SARM) i ich zastosowania |
| EP2244576A4 (en) * | 2008-01-24 | 2011-06-08 | Merck Sharp & Dohme | 3,5-substituted-1,3-oxazolidine-2-one derivatives |
| CN106572997A (zh) | 2014-05-30 | 2017-04-19 | 辉瑞公司 | 作为选择性雄激素受体调节剂的腈衍生物 |
| MX2021012690A (es) | 2019-04-19 | 2022-01-31 | Ligand Pharm Inc | Formas cristalinas y metodos para producir formas cristalinas de un compuesto. |
| WO2023275715A1 (en) | 2021-06-30 | 2023-01-05 | Pfizer Inc. | Metabolites of selective androgen receptor modulators |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE791501A (fr) * | 1971-11-19 | 1973-05-17 | Albert Ag Chem Werke | Diamines cycliques n,n'-disubstituees et leur procede de preparation |
| US4062862A (en) * | 1975-07-04 | 1977-12-13 | Nippon Chemiphar Co., Ltd. | 5-Benzyl-2-oxazolidone derivatives and a process for producing the same |
| US4602093A (en) * | 1984-02-08 | 1986-07-22 | Merck & Co., Inc. | Novel substituted imidazoles, their preparation and use |
| DE3723797A1 (de) * | 1987-07-18 | 1989-01-26 | Merck Patent Gmbh | Oxazolidinone |
| CA1320730C (en) * | 1987-10-16 | 1993-07-27 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl aroylbenzene derivatives useful as antibacterial agents |
| US5053393A (en) * | 1988-07-20 | 1991-10-01 | Monsanto Company | Novel platelet-aggregation inhibitor |
| US5084466A (en) * | 1989-01-31 | 1992-01-28 | Hoffmann-La Roche Inc. | Novel carboxamide pyridine compounds which have useful pharmaceutical utility |
| DE4005371A1 (de) * | 1990-02-21 | 1991-08-22 | Merck Patent Gmbh | Oxazolidinone |
| DE4017211A1 (de) * | 1990-05-29 | 1991-12-05 | Merck Patent Gmbh | Oxazolidinone |
| WO1993022298A1 (fr) * | 1992-04-30 | 1993-11-11 | Taiho Pharmaceutical Co., Ltd. | Derive d'oxazolidine et son sel pharmaceutiquement acceptable |
| US5532225A (en) * | 1992-07-31 | 1996-07-02 | Sri International | Acyclic purine phosphonate nucleotide analogs as antiviral agents, and related synthetic methods |
| ES2134870T3 (es) * | 1993-05-01 | 1999-10-16 | Merck Patent Gmbh | Antagonistas del receptor de adhesion. |
| IL109570A0 (en) * | 1993-05-17 | 1994-08-26 | Fujisawa Pharmaceutical Co | Guanidine derivatives, pharmaceutical compositions containing the same and processes for the preparation thereof |
| DE4324393A1 (de) * | 1993-07-21 | 1995-01-26 | Merck Patent Gmbh | 4-Aryloxy- und 4-Arylthiopiperidinderivate |
| DE4332384A1 (de) * | 1993-09-23 | 1995-03-30 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten III |
| TW286317B (cs) * | 1993-12-13 | 1996-09-21 | Hoffmann La Roche | |
| DE4439846A1 (de) * | 1994-11-08 | 1996-05-09 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
| TW363051B (en) * | 1995-08-31 | 1999-07-01 | Mitsui Toatsu Chemicals | Substituted amidine derivatives and platelet aggregation inhibitor containing the same |
-
1993
- 1993-09-23 DE DE4332384A patent/DE4332384A1/de not_active Withdrawn
-
1994
- 1994-08-01 UA UA94085682A patent/UA40590C2/uk unknown
- 1994-09-14 CZ CZ19942247A patent/CZ288819B6/cs not_active IP Right Cessation
- 1994-09-15 AT AT94114519T patent/ATE178599T1/de not_active IP Right Cessation
- 1994-09-15 ES ES94114519T patent/ES2132295T3/es not_active Expired - Lifetime
- 1994-09-15 EP EP94114519A patent/EP0645376B1/de not_active Expired - Lifetime
- 1994-09-15 DE DE59408068T patent/DE59408068D1/de not_active Expired - Fee Related
- 1994-09-15 DK DK94114519T patent/DK0645376T3/da active
- 1994-09-16 AU AU73050/94A patent/AU682050B2/en not_active Ceased
- 1994-09-19 SK SK1121-94A patent/SK282134B6/sk unknown
- 1994-09-20 CN CN94115356A patent/CN1052227C/zh not_active Expired - Fee Related
- 1994-09-20 JP JP6224941A patent/JPH07179441A/ja not_active Withdrawn
- 1994-09-21 TW TW083108683A patent/TW381086B/zh not_active IP Right Cessation
- 1994-09-21 CA CA002132579A patent/CA2132579A1/en not_active Abandoned
- 1994-09-22 US US08/310,085 patent/US5561148A/en not_active Expired - Fee Related
- 1994-09-22 ZA ZA947405A patent/ZA947405B/xx unknown
- 1994-09-22 HU HU9402724A patent/HU217980B/hu not_active IP Right Cessation
- 1994-09-22 PL PL94305144A patent/PL180462B1/pl unknown
- 1994-09-22 KR KR1019940023840A patent/KR100347849B1/ko not_active Expired - Fee Related
- 1994-09-22 NO NO943523A patent/NO305203B1/no not_active IP Right Cessation
- 1994-09-23 RU RU94034124A patent/RU2125560C1/ru not_active IP Right Cessation
-
1996
- 1996-05-29 US US08/654,690 patent/US5723480A/en not_active Expired - Fee Related
-
1997
- 1997-11-06 US US08/964,131 patent/US6028090A/en not_active Expired - Fee Related
-
1999
- 1999-06-15 GR GR990401587T patent/GR3030512T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0645376B1 (de) | 1999-04-07 |
| CZ288819B6 (cs) | 2001-09-12 |
| AU682050B2 (en) | 1997-09-18 |
| TW381086B (en) | 2000-02-01 |
| NO943523L (no) | 1995-03-24 |
| US5723480A (en) | 1998-03-03 |
| SK112194A3 (en) | 1995-05-10 |
| UA40590C2 (uk) | 2001-08-15 |
| HU217980B (hu) | 2000-05-28 |
| GR3030512T3 (en) | 1999-10-29 |
| PL180462B1 (pl) | 2001-02-28 |
| ZA947405B (en) | 1995-05-15 |
| EP0645376A1 (de) | 1995-03-29 |
| US5561148A (en) | 1996-10-01 |
| DK0645376T3 (da) | 1999-10-18 |
| HUT71233A (en) | 1995-11-28 |
| DE4332384A1 (de) | 1995-03-30 |
| RU2125560C1 (ru) | 1999-01-27 |
| CZ224794A3 (en) | 1995-07-12 |
| CN1052227C (zh) | 2000-05-10 |
| CN1106806A (zh) | 1995-08-16 |
| US6028090A (en) | 2000-02-22 |
| RU94034124A (ru) | 1996-07-10 |
| PL305144A1 (en) | 1995-04-03 |
| NO943523D0 (no) | 1994-09-22 |
| AU7305094A (en) | 1995-04-06 |
| ATE178599T1 (de) | 1999-04-15 |
| KR100347849B1 (ko) | 2002-11-16 |
| HU9402724D0 (en) | 1994-12-28 |
| JPH07179441A (ja) | 1995-07-18 |
| CA2132579A1 (en) | 1995-03-24 |
| DE59408068D1 (de) | 1999-05-12 |
| NO305203B1 (no) | 1999-04-19 |
| ES2132295T3 (es) | 1999-08-16 |
| KR950008493A (ko) | 1995-04-17 |
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