NO310194B1 - Nye oksazolidinonderivater, farmasöytiske preparater som inneholder dem, samt anvendelse av disse forbindelsene tilfremstilling av legemidler - Google Patents
Nye oksazolidinonderivater, farmasöytiske preparater som inneholder dem, samt anvendelse av disse forbindelsene tilfremstilling av legemidler Download PDFInfo
- Publication number
- NO310194B1 NO310194B1 NO19980059A NO980059A NO310194B1 NO 310194 B1 NO310194 B1 NO 310194B1 NO 19980059 A NO19980059 A NO 19980059A NO 980059 A NO980059 A NO 980059A NO 310194 B1 NO310194 B1 NO 310194B1
- Authority
- NO
- Norway
- Prior art keywords
- oxo
- ylmethyl
- oxazolidin
- tetrahydro
- carboxylic acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 63
- 239000003814 drug Substances 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 4
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- XJASBPKXGAVAGE-NRFANRHFSA-N 1-[[(5s)-5-methyl-2-oxo-3-(1-pyridin-4-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylic acid Chemical compound C([C@]1(C)OC(=O)N(C2CCN(CC2)C=2C=CN=CC=2)C1)N1CCC(C(O)=O)CC1 XJASBPKXGAVAGE-NRFANRHFSA-N 0.000 claims description 2
- LGYNXXFXUCDUOC-UHFFFAOYSA-N 1-[[2-oxo-3-(1-pyridin-4-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC1OC(=O)N(C2CCN(CC2)C=2C=CN=CC=2)C1 LGYNXXFXUCDUOC-UHFFFAOYSA-N 0.000 claims description 2
- SXRDTEFQRHMFPM-UHFFFAOYSA-N 1-[[2-oxo-3-(1-pyridin-4-ylpiperidin-4-yl)-4-[3-(trifluoromethyl)phenyl]-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC1C(C=2C=C(C=CC=2)C(F)(F)F)N(C2CCN(CC2)C=2C=CN=CC=2)C(=O)O1 SXRDTEFQRHMFPM-UHFFFAOYSA-N 0.000 claims description 2
- RKSCTOQQQJRZGM-UHFFFAOYSA-N 1-[[2-oxo-3-(1-pyrimidin-4-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC1OC(=O)N(C2CCN(CC2)C=2N=CN=CC=2)C1 RKSCTOQQQJRZGM-UHFFFAOYSA-N 0.000 claims description 2
- PBEXCDXVGZUDGF-UHFFFAOYSA-N 1-[[3-[1-[2-(benzylamino)pyrimidin-4-yl]piperidin-4-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC1OC(=O)N(C2CCN(CC2)C=2N=C(NCC=3C=CC=CC=3)N=CC=2)C1 PBEXCDXVGZUDGF-UHFFFAOYSA-N 0.000 claims description 2
- OTFFIRCVXYJRGP-UHFFFAOYSA-N 1-[[4-(4-chlorophenyl)-2-oxo-3-(1-pyridin-4-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC1C(C=2C=CC(Cl)=CC=2)N(C2CCN(CC2)C=2C=CN=CC=2)C(=O)O1 OTFFIRCVXYJRGP-UHFFFAOYSA-N 0.000 claims description 2
- MDKOEMUHBNBSOX-UHFFFAOYSA-N 2-[1-[[2-oxo-3-(1-pyridin-4-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]methyl]piperidin-4-ylidene]acetic acid Chemical compound C1CC(=CC(=O)O)CCN1CC1OC(=O)N(C2CCN(CC2)C=2C=CN=CC=2)C1 MDKOEMUHBNBSOX-UHFFFAOYSA-N 0.000 claims description 2
- 229910014033 C-OH Inorganic materials 0.000 claims description 2
- 229910014570 C—OH Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- LGYNXXFXUCDUOC-SFHVURJKSA-N 1-[[(5s)-2-oxo-3-(1-pyridin-4-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C[C@@H]1OC(=O)N(C2CCN(CC2)C=2C=CN=CC=2)C1 LGYNXXFXUCDUOC-SFHVURJKSA-N 0.000 claims 1
- SEUCIWYDTWRATP-UHFFFAOYSA-N 1-[[4-methyl-2-oxo-3-(1-pyridin-4-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylic acid Chemical compound O1C(=O)N(C2CCN(CC2)C=2C=CN=CC=2)C(C)C1CN1CCC(C(O)=O)CC1 SEUCIWYDTWRATP-UHFFFAOYSA-N 0.000 claims 1
- DVJUGEZMMDDDEW-UHFFFAOYSA-N 2-[4-hydroxy-1-[[2-oxo-3-(1-pyridin-4-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]methyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)(O)CCN1CC1OC(=O)N(C2CCN(CC2)C=2C=CN=CC=2)C1 DVJUGEZMMDDDEW-UHFFFAOYSA-N 0.000 claims 1
- HGYAMVKFPZZMCT-UHFFFAOYSA-N 4-hydroxy-4-[[2-oxo-3-(1-pyridin-4-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]methyl]cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1(O)CC1OC(=O)N(C2CCN(CC2)C=2C=CN=CC=2)C1 HGYAMVKFPZZMCT-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 55
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- 238000000034 method Methods 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 239000000843 powder Substances 0.000 description 20
- 150000001412 amines Chemical class 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 235000011121 sodium hydroxide Nutrition 0.000 description 17
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 150000002924 oxiranes Chemical class 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- 125000004494 ethyl ester group Chemical group 0.000 description 11
- -1 methylene, ethylene, carbonyl Chemical group 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
- 150000002576 ketones Chemical class 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 9
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 150000001540 azides Chemical class 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001414 amino alcohols Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- KPKNTUUIEVXMOH-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decane Chemical compound O1CCOC11CCNCC1 KPKNTUUIEVXMOH-UHFFFAOYSA-N 0.000 description 4
- 102000008946 Fibrinogen Human genes 0.000 description 4
- 108010049003 Fibrinogen Proteins 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 244000309464 bull Species 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229940012952 fibrinogen Drugs 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 4
- 238000002953 preparative HPLC Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 238000007239 Wittig reaction Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- RUJPPJYDHHAEEK-UHFFFAOYSA-N ethyl piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCNCC1 RUJPPJYDHHAEEK-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 229960003975 potassium Drugs 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- VSSYHWNIKWNOQH-UHFFFAOYSA-N 8-(2-chloropyrimidin-4-yl)-1,4-dioxa-8-azaspiro[4.5]decane Chemical compound ClC1=NC=CC(N2CCC3(CC2)OCCO3)=N1 VSSYHWNIKWNOQH-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 210000001772 blood platelet Anatomy 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000006567 deketalization reaction Methods 0.000 description 2
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 2
- KOWAIRDYUSKJSH-UHFFFAOYSA-N ethyl 1-(3-amino-2-hydroxypropyl)piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCN(CC(O)CN)CC1 KOWAIRDYUSKJSH-UHFFFAOYSA-N 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
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- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
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- HRXSKIOIHQEGAI-UHFFFAOYSA-M diethylalumanylium;fluoride Chemical compound CC[Al](F)CC HRXSKIOIHQEGAI-UHFFFAOYSA-M 0.000 description 1
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- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- YJMVJGVGCBULJQ-UHFFFAOYSA-N ethyl 1-(3-amino-2-hydroxybutyl)piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCN(CC(O)C(C)N)CC1 YJMVJGVGCBULJQ-UHFFFAOYSA-N 0.000 description 1
- VBQJJXYWFVEXMV-UHFFFAOYSA-N ethyl 1-(3-azido-2-hydroxybutyl)piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCN(CC(O)C(C)N=[N+]=[N-])CC1 VBQJJXYWFVEXMV-UHFFFAOYSA-N 0.000 description 1
- IBPUOYTZNYPDFB-UHFFFAOYSA-N ethyl 1-(3-azido-2-hydroxypropyl)piperidine-4-carboxylate Chemical compound CCOC(=O)C1CCN(CC(O)CN=[N+]=[N-])CC1 IBPUOYTZNYPDFB-UHFFFAOYSA-N 0.000 description 1
- DGFHSYNZOXSYOK-UHFFFAOYSA-N ethyl 1-(oxiran-2-ylmethyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1OC1 DGFHSYNZOXSYOK-UHFFFAOYSA-N 0.000 description 1
- QIHVRCWRXAPWFB-UHFFFAOYSA-N ethyl 1-[2-hydroxy-3-[(1-pyrimidin-4-ylpiperidin-4-yl)amino]propyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC(O)CNC1CCN(C=2N=CN=CC=2)CC1 QIHVRCWRXAPWFB-UHFFFAOYSA-N 0.000 description 1
- QCJVQWDCNWTJIZ-UHFFFAOYSA-N ethyl 1-[2-hydroxy-3-[[1-(2-pyridin-4-ylethyl)piperidin-4-yl]amino]propyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC(O)CNC1CCN(CCC=2C=CN=CC=2)CC1 QCJVQWDCNWTJIZ-UHFFFAOYSA-N 0.000 description 1
- SVBKCOICIZBTAJ-UHFFFAOYSA-N ethyl 1-[3-[[1-[2-(benzylamino)pyrimidin-4-yl]piperidin-4-yl]amino]-2-hydroxypropyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC(O)CNC1CCN(C=2N=C(NCC=3C=CC=CC=3)N=CC=2)CC1 SVBKCOICIZBTAJ-UHFFFAOYSA-N 0.000 description 1
- DGFHSYNZOXSYOK-JTQLQIEISA-N ethyl 1-[[(2s)-oxiran-2-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C[C@@H]1OC1 DGFHSYNZOXSYOK-JTQLQIEISA-N 0.000 description 1
- XCAWGGONMUGHPF-UHFFFAOYSA-N ethyl 1-[[4-methyl-2-oxo-3-(1-pyridin-4-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CC1C(C)N(C2CCN(CC2)C=2C=CN=CC=2)C(=O)O1 XCAWGGONMUGHPF-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XIWBSOUNZWSFKU-UHFFFAOYSA-N ethyl piperidine-3-carboxylate Chemical compound CCOC(=O)C1CCCNC1 XIWBSOUNZWSFKU-UHFFFAOYSA-N 0.000 description 1
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- 150000003840 hydrochlorides Chemical class 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- 238000004949 mass spectrometry Methods 0.000 description 1
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- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical group COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 208000010125 myocardial infarction Diseases 0.000 description 1
- APBBAQCENVXUHL-UHFFFAOYSA-N n,n-diethylethanamine;2,2,2-trifluoroacetic acid Chemical compound CCN(CC)CC.OC(=O)C(F)(F)F APBBAQCENVXUHL-UHFFFAOYSA-N 0.000 description 1
- OGHQEIZTDAAANQ-UHFFFAOYSA-N n-benzyl-4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)pyrimidin-2-amine Chemical compound C=1C=CC=CC=1CNC(N=1)=NC=CC=1N(CC1)CCC21OCCO2 OGHQEIZTDAAANQ-UHFFFAOYSA-N 0.000 description 1
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- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- LTEKQAPRXFBRNN-UHFFFAOYSA-N piperidin-4-ylmethanamine Chemical compound NCC1CCNCC1 LTEKQAPRXFBRNN-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- BXRVYRPLDNEVED-UHFFFAOYSA-N tert-butyl 2-[4-hydroxy-1-[[2-oxo-3-(1-pyridin-4-ylpiperidin-4-yl)-1,3-oxazolidin-5-yl]methyl]piperidin-4-yl]acetate Chemical compound C1CC(CC(=O)OC(C)(C)C)(O)CCN1CC1OC(=O)N(C2CCN(CC2)C=2C=CN=CC=2)C1 BXRVYRPLDNEVED-UHFFFAOYSA-N 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
- 238000012360 testing method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- ZWYDDDAMNQQZHD-UHFFFAOYSA-L titanium(ii) chloride Chemical compound [Cl-].[Cl-].[Ti+2] ZWYDDDAMNQQZHD-UHFFFAOYSA-L 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- XWNXEWLCHSLQOI-UHFFFAOYSA-K trisodium;triacetate Chemical compound [Na+].[Na+].[Na+].CC([O-])=O.CC([O-])=O.CC([O-])=O XWNXEWLCHSLQOI-UHFFFAOYSA-K 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19524765A DE19524765A1 (de) | 1995-07-07 | 1995-07-07 | Neue Oxazolidinonderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
PCT/EP1996/002939 WO1997003072A1 (de) | 1995-07-07 | 1996-07-04 | Neue oxazolidinonderivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
Publications (3)
Publication Number | Publication Date |
---|---|
NO980059D0 NO980059D0 (no) | 1998-01-06 |
NO980059L NO980059L (no) | 1998-01-06 |
NO310194B1 true NO310194B1 (no) | 2001-06-05 |
Family
ID=7766252
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19980059A NO310194B1 (no) | 1995-07-07 | 1998-01-06 | Nye oksazolidinonderivater, farmasöytiske preparater som inneholder dem, samt anvendelse av disse forbindelsene tilfremstilling av legemidler |
Country Status (19)
Country | Link |
---|---|
US (1) | US5972947A (de) |
EP (1) | EP0839147A1 (de) |
JP (1) | JPH11508904A (de) |
KR (1) | KR19990028792A (de) |
CN (1) | CN1195348A (de) |
AU (1) | AU709208B2 (de) |
BR (1) | BR9609327A (de) |
CA (1) | CA2225411A1 (de) |
CZ (1) | CZ288619B6 (de) |
DE (1) | DE19524765A1 (de) |
HU (1) | HUP9900348A3 (de) |
IL (1) | IL122815A0 (de) |
NO (1) | NO310194B1 (de) |
NZ (1) | NZ313599A (de) |
PL (1) | PL324436A1 (de) |
SK (1) | SK298A3 (de) |
TW (1) | TW332206B (de) |
WO (1) | WO1997003072A1 (de) |
ZA (1) | ZA965712B (de) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HUP9901741A3 (en) * | 1996-03-30 | 2000-03-28 | Roche Diagnostics Gmbh | Novel oxazolidine derivatives, process for their production and medicaments containing them |
AR012443A1 (es) * | 1997-04-16 | 2000-10-18 | Uriach & Cia Sa J | Nuevas carboxamidas como inhibidores de la agregacion plaquetaria, procedimiento para su preparacion, composiciones farmaceuticas que loscontienen y uso de los mismos en la manufactura de medicamentos |
AR013693A1 (es) * | 1997-10-23 | 2001-01-10 | Uriach & Cia Sa J | Nuevas piperidinas y piperazinas como inhibidores de la agregacion plaquetaria |
DE19962924A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
DE10129725A1 (de) * | 2001-06-20 | 2003-01-02 | Bayer Ag | Kombinationstherapie substituierter Oxazolidinone |
AU2003235895A1 (en) * | 2002-05-09 | 2003-11-11 | Mochida Pharmaceutical Co., Ltd. | Process for producing 1-(4-pyridyl)-4-piperidone |
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 |
EP1805165B1 (de) * | 2004-10-18 | 2009-12-16 | Eli Lilly And Company | 1-(hetero)aryl-3-aminopyrrolidinderivate zur verwendung als antagonisten des mglur3-rezeptors |
DE102004062475A1 (de) * | 2004-12-24 | 2006-07-06 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit modifizierter Freisetzung |
EP1685841A1 (de) | 2005-01-31 | 2006-08-02 | Bayer Health Care Aktiengesellschaft | Prophylaxe und Behandlung von thrombolischen Erkrankungen |
DE102005045518A1 (de) | 2005-09-23 | 2007-03-29 | Bayer Healthcare Ag | 2-Aminoethoxyessigsäure-Derivate und ihre Verwendung |
DE102005047561A1 (de) | 2005-10-04 | 2007-04-05 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit schneller Wirkstofffreisetzung |
DE102005047558A1 (de) * | 2005-10-04 | 2008-02-07 | Bayer Healthcare Ag | Kombinationstherapie substituierter Oxazolidinone zur Prophylaxe und Behandlung von cerebralen Durchblutungsstörungen |
EP1934208B1 (de) | 2005-10-04 | 2011-03-23 | Bayer Schering Pharma Aktiengesellschaft | Neue polymorphe form von 5-chlor-n-({ ( 5s )-2-0x0-3-[4-( 3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl} -methyl)-2-thiophencarboxamid |
DE102005048824A1 (de) * | 2005-10-10 | 2007-04-12 | Bayer Healthcare Ag | Behandlung und Prophylaxe von Mikroangiopathien |
DE102006051625A1 (de) * | 2006-11-02 | 2008-05-08 | Bayer Materialscience Ag | Kombinationstherapie substituierter Oxazolidinone |
DE102007018662A1 (de) | 2007-04-20 | 2008-10-23 | Bayer Healthcare Ag | Oxazolidinone zur Behandlung und Prophylaxe von pulmonaler Hypertonie |
DE102007028318A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Oxazolidinone zur Behandlung und Prophylaxe von Sepsis |
EP2138178A1 (de) | 2008-06-28 | 2009-12-30 | Bayer Schering Pharma Aktiengesellschaft | Oxazolidninone zur Behandlung der chronisch obstruktiven Lungenerkrankung (COPD) und/oder Asthma |
EP2140866A1 (de) | 2008-07-04 | 2010-01-06 | Bayer Schering Pharma Aktiengesellschaft | Oxazolidinone zur Behandlung von Entzündungserkrankungen des Magen-Darm-Trakts |
WO2014085413A1 (en) * | 2012-11-28 | 2014-06-05 | Temple University - Of The Commonwealth System Of Higher Education | Disubstituted oxazolidin-2-ones 5-hydroxytryptamine receptor 2b activity modulators |
CN105829304B (zh) * | 2013-12-20 | 2019-09-20 | 中国人民解放军军事医学科学院毒物药物研究所 | N,n’取代哌啶胺类化合物、其制备方法及用途 |
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GB9122016D0 (en) * | 1991-10-16 | 1991-11-27 | Glaxo Group Ltd | Chemical compounds |
WO1993014077A1 (en) * | 1992-01-21 | 1993-07-22 | Glaxo Group Limited | Piperidineacetic acid derivatives as inhibitors of fibrinogen-dependent blood platelet aggregation |
PT825184E (pt) * | 1993-03-29 | 2001-11-30 | Astrazeneca Ab | Derivados heterociclicos como inibidores de agregacao de plaquetas |
DK0623615T3 (da) * | 1993-05-01 | 1999-12-13 | Merck Patent Gmbh | Adhæsionsreceptor-antagonister |
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 |
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1995
- 1995-07-07 DE DE19524765A patent/DE19524765A1/de not_active Withdrawn
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1996
- 1996-07-02 TW TW085108000A patent/TW332206B/zh active
- 1996-07-04 KR KR1019980700092A patent/KR19990028792A/ko not_active Application Discontinuation
- 1996-07-04 BR BR9609327A patent/BR9609327A/pt not_active Application Discontinuation
- 1996-07-04 CA CA002225411A patent/CA2225411A1/en not_active Abandoned
- 1996-07-04 JP JP9505482A patent/JPH11508904A/ja active Pending
- 1996-07-04 AU AU66113/96A patent/AU709208B2/en not_active Ceased
- 1996-07-04 CN CN96196744A patent/CN1195348A/zh active Pending
- 1996-07-04 NZ NZ313599A patent/NZ313599A/en unknown
- 1996-07-04 HU HU9900348A patent/HUP9900348A3/hu unknown
- 1996-07-04 WO PCT/EP1996/002939 patent/WO1997003072A1/de not_active Application Discontinuation
- 1996-07-04 CZ CZ19974233A patent/CZ288619B6/cs not_active IP Right Cessation
- 1996-07-04 SK SK2-98A patent/SK298A3/sk unknown
- 1996-07-04 PL PL96324436A patent/PL324436A1/xx unknown
- 1996-07-04 EP EP96925657A patent/EP0839147A1/de not_active Withdrawn
- 1996-07-04 IL IL12281596A patent/IL122815A0/xx unknown
- 1996-07-05 ZA ZA9605712A patent/ZA965712B/xx unknown
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1998
- 1998-01-06 NO NO19980059A patent/NO310194B1/no not_active IP Right Cessation
- 1998-12-31 US US09/224,799 patent/US5972947A/en not_active Expired - Fee Related
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MX9800157A (es) | 1998-03-29 |
KR19990028792A (ko) | 1999-04-15 |
CA2225411A1 (en) | 1997-01-30 |
NZ313599A (en) | 1999-10-28 |
TW332206B (en) | 1998-05-21 |
HUP9900348A2 (hu) | 1999-05-28 |
CZ423397A3 (cs) | 1998-03-18 |
US5972947A (en) | 1999-10-26 |
ZA965712B (en) | 1998-01-05 |
EP0839147A1 (de) | 1998-05-06 |
CN1195348A (zh) | 1998-10-07 |
JPH11508904A (ja) | 1999-08-03 |
HUP9900348A3 (en) | 2000-11-28 |
IL122815A0 (en) | 1998-08-16 |
NO980059D0 (no) | 1998-01-06 |
SK298A3 (en) | 1998-05-06 |
PL324436A1 (en) | 1998-05-25 |
WO1997003072A1 (de) | 1997-01-30 |
DE19524765A1 (de) | 1997-01-09 |
BR9609327A (pt) | 1999-05-25 |
AU6611396A (en) | 1997-02-10 |
NO980059L (no) | 1998-01-06 |
CZ288619B6 (cs) | 2001-08-15 |
AU709208B2 (en) | 1999-08-26 |
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