SK298A3 - New oxazolidinone derivatives, process for preparing the same and medicaments that contain these compounds - Google Patents

New oxazolidinone derivatives, process for preparing the same and medicaments that contain these compounds Download PDF

Info

Publication number: SK298A3
Authority: SK; Slovakia
Prior art keywords: oxo; tetrahydro; bipyridinyl; oxazolidin; piperidine
Prior art date: 1995-07-07

Application number

SK2-98A

Other languages

English (en)

Slovak (sk)

Inventor

Christos Tsaklakidis

Wolfgang Schafer

Liesel Dorge

Walter-Gunar Friebe

Angelika Esswein

Original Assignee

Boehringer Mannheim Gmbh

Priority date (The priority date 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 date listed.)

1995-07-07

Filing date

1996-07-04

Publication date

1998-05-06

1996-07-04 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1998-05-06 Publication of SK298A3 publication Critical patent/SK298A3/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 64
239000003814 drug Substances 0.000 title claims abstract description 5
238000004519 manufacturing process Methods 0.000 title claims abstract 3
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
239000001257 hydrogen Substances 0.000 claims abstract description 33
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
150000002431 hydrogen Chemical class 0.000 claims abstract description 18
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
125000003118 aryl group Chemical group 0.000 claims abstract description 9
125000002252 acyl group Chemical group 0.000 claims abstract description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 6
125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 6
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 6
239000000126 substance Substances 0.000 claims abstract description 4
229910014033 C-OH Inorganic materials 0.000 claims abstract description 3
229910014570 C—OH Inorganic materials 0.000 claims abstract description 3
125000002947 alkylene group Chemical group 0.000 claims abstract description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 80
239000002253 acid Substances 0.000 claims description 48
-1 3-trifluoromethylphenyl Chemical group 0.000 claims description 35
SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 12
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 7
VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 4
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 3
239000000969 carrier Substances 0.000 claims description 3
208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
125000001072 heteroaryl group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 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 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 52
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 43
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
238000005160 1H NMR spectroscopy Methods 0.000 description 31
229960000583 acetic acid Drugs 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
239000002904 solvent Substances 0.000 description 25
239000000203 mixture Substances 0.000 description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
238000000034 method Methods 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 20
239000000843 powder Substances 0.000 description 20
125000004494 ethyl ester group Chemical group 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
150000001412 amines Chemical class 0.000 description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
235000011121 sodium hydroxide Nutrition 0.000 description 16
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
239000003921 oil Substances 0.000 description 15
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 14
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 14
150000002924 oxiranes Chemical class 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
229910052938 sodium sulfate Inorganic materials 0.000 description 13
235000011152 sodium sulphate Nutrition 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
238000001035 drying Methods 0.000 description 11
150000002576 ketones Chemical class 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
150000001540 azides Chemical class 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 6
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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
229910052799 carbon Inorganic materials 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
239000000872 buffer Substances 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
239000012043 crude product Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
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 5
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 4
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 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
239000000654 additive Substances 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
239000008346 aqueous phase Substances 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
230000015572 biosynthetic process Effects 0.000 description 4
244000309464 bull Species 0.000 description 4
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 4
150000002902 organometallic compounds Chemical class 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
229910000027 potassium carbonate Inorganic materials 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
238000002953 preparative HPLC Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
238000010992 reflux Methods 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
238000003756 stirring Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
KPKNTUUIEVXMOH-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decane Chemical compound O1CCOC11CCNCC1 KPKNTUUIEVXMOH-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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
102000008946 Fibrinogen Human genes 0.000 description 3
108010049003 Fibrinogen Proteins 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
238000007239 Wittig reaction Methods 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 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
239000000284 extract Substances 0.000 description 3
229940012952 fibrinogen Drugs 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000002390 rotary evaporation Methods 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-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
DZCYWXRQXJNBAZ-UHFFFAOYSA-N 1-[[2-oxo-4-phenyl-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=CC=2)N(C2CCN(CC2)C=2C=CN=CC=2)C(=O)O1 DZCYWXRQXJNBAZ-UHFFFAOYSA-N 0.000 description 2
125000000094 2-phenylethyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
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 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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
238000002965 ELISA Methods 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000003556 assay Methods 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
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239000007924 injection Substances 0.000 description 2
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230000037361 pathway Effects 0.000 description 2
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JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
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TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
LMCBEWMQFKWHGU-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O LMCBEWMQFKWHGU-UHFFFAOYSA-N 0.000 description 1
VDGHMPYWAXDFGS-UHFFFAOYSA-N propan-2-ol;titanium(4+) Chemical compound [Ti+4].CC(C)O VDGHMPYWAXDFGS-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000004892 pyridazines Chemical class 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
229910003450 rhodium oxide Inorganic materials 0.000 description 1
GWKCACMSZXJZEW-UHFFFAOYSA-H rhodium(3+);tricarbonate Chemical compound [Rh+3].[Rh+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O GWKCACMSZXJZEW-UHFFFAOYSA-H 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
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 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
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
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
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 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
WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
ZVQXQPNJHRNGID-UHFFFAOYSA-N tetramethylsuccinonitrile Chemical compound N#CC(C)(C)C(C)(C)C#N ZVQXQPNJHRNGID-UHFFFAOYSA-N 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
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Diabetes (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Hematology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SK2-98A 1995-07-07 1996-07-04 New oxazolidinone derivatives, process for preparing the same and medicaments that contain these compounds SK298A3 (en)

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 (fr)	1995-07-07	1996-07-04	Derives nouveaux d'oxazolidinone, leur procede de preparation et medicaments contenant ces composes

Publications (1)

Publication Number	Publication Date
SK298A3 true SK298A3 (en)	1998-05-06

Family

ID=7766252

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK2-98A SK298A3 (en)	1995-07-07	1996-07-04	New oxazolidinone derivatives, process for preparing the same and medicaments that contain these compounds

Country Status (19)

Country	Link
US (1)	US5972947A (fr)
EP (1)	EP0839147A1 (fr)
JP (1)	JPH11508904A (fr)
KR (1)	KR19990028792A (fr)
CN (1)	CN1195348A (fr)
AU (1)	AU709208B2 (fr)
BR (1)	BR9609327A (fr)
CA (1)	CA2225411A1 (fr)
CZ (1)	CZ288619B6 (fr)
DE (1)	DE19524765A1 (fr)
HU (1)	HUP9900348A3 (fr)
IL (1)	IL122815A0 (fr)
NO (1)	NO310194B1 (fr)
NZ (1)	NZ313599A (fr)
PL (1)	PL324436A1 (fr)
SK (1)	SK298A3 (fr)
TW (1)	TW332206B (fr)
WO (1)	WO1997003072A1 (fr)
ZA (1)	ZA965712B (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PL329053A1 (en) *	1996-03-30	1999-03-01	Roche Diagnostics Gmbh	Novel derivatives of oxazolydine, method of obtaining them and therapeutic agents containing such compounds
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
JPWO2003095446A1 (ja) *	2002-05-09	2005-09-15	持田製薬株式会社	１−（４−ピリジル）−４−ピペリドンの製造方法
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
MX2007004661A (es) *	2004-10-18	2007-06-22	Lilly Co Eli	Derivados de 1-(hetero)aril-3-amino-pirrolidina para usarse como antagonistas del receptor mglur3.
DE102004062475A1 (de) *	2004-12-24	2006-07-06	Bayer Healthcare Ag	Feste, oral applizierbare pharmazeutische Darreichungsformen mit modifizierter Freisetzung
EP1685841A1 (fr)	2005-01-31	2006-08-02	Bayer Health Care Aktiengesellschaft	Prevention et traitement de troubles thromboemboliques
DE102005045518A1 (de)	2005-09-23	2007-03-29	Bayer Healthcare Ag	2-Aminoethoxyessigsäure-Derivate und ihre Verwendung
AU2006299126B2 (en)	2005-10-04	2012-06-28	Bayer Intellectual Property Gmbh	Novel polymorphous form and the amorphous form of 5-chloro-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidine-5-yl}-methyl)-2-thiophene carboxamide
DE102005047558A1 (de) *	2005-10-04	2008-02-07	Bayer Healthcare Ag	Kombinationstherapie substituierter Oxazolidinone zur Prophylaxe und Behandlung von cerebralen Durchblutungsstörungen
DE102005047561A1 (de)	2005-10-04	2007-04-05	Bayer Healthcare Ag	Feste, oral applizierbare pharmazeutische Darreichungsformen mit schneller Wirkstofffreisetzung
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 (fr)	2008-06-28	2009-12-30	Bayer Schering Pharma Aktiengesellschaft	Oxazolidinones pour le traitement de maladie pulmonaire obstructive chronique (MPOC) et/ou de l'asthme
EP2140866A1 (fr)	2008-07-04	2010-01-06	Bayer Schering Pharma Aktiengesellschaft	Oxazolidinones pour le traitement d'états inflammatoires du tractus gastro-intestinal
US9464062B2 (en)	2012-11-28	2016-10-11	Temple University—Of the Commonwealth System of Higher Education	Disubstituted oxazolidin-2-ones 5-hydroxytryptamine receptor 2B activity modulators
WO2015090226A1 (fr) *	2013-12-20	2015-06-25	中国人民解放军军事医学科学院毒物药物研究所	Composés n,n'-substitués de pipéridinamine, leurs procédés de préparation et utilisation correspondante

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GB9122016D0 (en) *	1991-10-16	1991-11-27	Glaxo Group Ltd	Chemical compounds
JPH07503459A (ja) *	1992-01-21	1995-04-13	グラクソ、グループ、リミテッド	酢酸誘導体
SK120895A3 (en) *	1993-03-29	1996-06-05	Zeneca Ltd	Pyridine derivatives, process for preparing the same and intermediate products in this process and pharmaceutical compositions containing them
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

1995
- 1995-07-07 DE DE19524765A patent/DE19524765A1/de not_active Withdrawn
1996
- 1996-07-02 TW TW085108000A patent/TW332206B/zh active
- 1996-07-04 HU HU9900348A patent/HUP9900348A3/hu unknown
- 1996-07-04 WO PCT/EP1996/002939 patent/WO1997003072A1/fr not_active Ceased
- 1996-07-04 JP JP9505482A patent/JPH11508904A/ja active Pending
- 1996-07-04 CZ CZ19974233A patent/CZ288619B6/cs not_active IP Right Cessation
- 1996-07-04 AU AU66113/96A patent/AU709208B2/en not_active Ceased
- 1996-07-04 NZ NZ313599A patent/NZ313599A/en unknown
- 1996-07-04 PL PL96324436A patent/PL324436A1/xx unknown
- 1996-07-04 BR BR9609327A patent/BR9609327A/pt not_active Application Discontinuation
- 1996-07-04 SK SK2-98A patent/SK298A3/sk unknown
- 1996-07-04 EP EP96925657A patent/EP0839147A1/fr not_active Withdrawn
- 1996-07-04 KR KR1019980700092A patent/KR19990028792A/ko not_active Withdrawn
- 1996-07-04 CA CA002225411A patent/CA2225411A1/fr not_active Abandoned
- 1996-07-04 CN CN96196744A patent/CN1195348A/zh active Pending
- 1996-07-04 IL IL12281596A patent/IL122815A0/xx unknown
- 1996-07-05 ZA ZA9605712A patent/ZA965712B/xx unknown
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

Also Published As

Publication number	Publication date
CZ288619B6 (cs)	2001-08-15
HUP9900348A3 (en)	2000-11-28
CZ423397A3 (cs)	1998-03-18
AU709208B2 (en)	1999-08-26
MX9800157A (es)	1998-03-29
NO980059L (no)	1998-01-06
NO980059D0 (no)	1998-01-06
CN1195348A (zh)	1998-10-07
KR19990028792A (ko)	1999-04-15
US5972947A (en)	1999-10-26
IL122815A0 (en)	1998-08-16
CA2225411A1 (fr)	1997-01-30
BR9609327A (pt)	1999-05-25
AU6611396A (en)	1997-02-10
PL324436A1 (en)	1998-05-25
EP0839147A1 (fr)	1998-05-06
WO1997003072A1 (fr)	1997-01-30
DE19524765A1 (de)	1997-01-09
NO310194B1 (no)	2001-06-05
NZ313599A (en)	1999-10-28
JPH11508904A (ja)	1999-08-03
HUP9900348A2 (hu)	1999-05-28
ZA965712B (en)	1998-01-05
TW332206B (en)	1998-05-21

Publication	Publication Date	Title
SK298A3 (en)	1998-05-06	New oxazolidinone derivatives, process for preparing the same and medicaments that contain these compounds
US8067457B2 (en)	2011-11-29	Compounds useful as antagonists of CCR2
JP6453231B2 (ja)	2019-01-16	ウレア誘導体、またはその薬理学的に許容される塩
EP2385040A1 (fr)	2011-11-09	Dérivés hétérocycliques renfermant de l'azote et médicaments contenant ces dérivés comme principe actif
MXPA01012450A (es)	2002-06-04	Inhibidores de metaloproteasas.
WO2001044200A2 (fr)	2001-06-21	Antagonistes selectifs de la neurokine
US20120035214A1 (en)	2012-02-09	Renin inhibitors
KR19990064178A (ko)	1999-07-26	1-(1,2-이치환된 피페리디닐)-4-치환된 피페라진 유도체
EP1646620B1 (fr)	2007-08-15	Piperidines substituees utilisees en tant que ligands du recepteur h3 de l'histamine
US5158947A (en)	1992-10-27	Condensed heterocyclic compounds and psychopharmaceutical composition containing same
CA2688057A1 (fr)	2008-11-27	Nouveaux inhibiteurs de rhenine
AU689587B2 (en)	1998-04-02	Dihygropyridine derivatives as bradykinin antagonists
AU722747B2 (en)	2000-08-10	Novel oxazolidine derivatives, process for their production and medicaments containing them
US20020147222A1 (en)	2002-10-10	Dihydropyridine derivatives
MXPA98000157A (en)	1998-10-15	New derivatives of oxazolidinone, processes to prepare the same and medicines that contain these compues
HU190793B (en)	1986-11-28	Process for preparing n-/ /4-phenyl-1,2,3,6-tetrahydro-pyridin-1-yl/-lakylene/-aza-spiro-alkane-diones and pharmaceutical compositions containing thereof as active substances
MXPA98008002A (en)	1999-04-06	New derivatives of oxazolidine, production processes and pharmaceutical agents containing these compues
DE19654479A1 (de)	1998-07-02	Neue Oxazolidinderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DE19612827A1 (de)	1997-10-02	Neue Oxazolidinonderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
EP1773823A1 (fr)	2007-04-18	Derives de 4-arylmorpholin-3-one, leur preparation et leur application en therapeutique
HK1080851A (en)	2006-05-04	Nitrogen-containing heterocyclic derivatives and drugs containing the same as the active ingredient
HK1021369A (en)	2000-06-09	Novel oxazolidine derivatives, process for their production and medicaments containing them