GB1588639A - 5-(substituted phenyl)-oxazolidinones and sulphur analogues thereof and also a process for their production - Google Patents
5-(substituted phenyl)-oxazolidinones and sulphur analogues thereof and also a process for their production Download PDFInfo
- Publication number
- GB1588639A GB1588639A GB50350/77A GB5035077A GB1588639A GB 1588639 A GB1588639 A GB 1588639A GB 50350/77 A GB50350/77 A GB 50350/77A GB 5035077 A GB5035077 A GB 5035077A GB 1588639 A GB1588639 A GB 1588639A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxazolidinone
- dimethoxyphenyl
- methoxyphenyl
- radical
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 11
- -1 5-(substituted phenyl)-oxazolidinones Chemical class 0.000 title claims description 56
- 238000000034 method Methods 0.000 title claims description 10
- 230000008569 process Effects 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- FWUOYEHWFKJVPM-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-1,3-oxazolidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1OC(=O)NC1 FWUOYEHWFKJVPM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 239000005864 Sulphur Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- VYYWZBLVFMZEPW-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-1,3-thiazolidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1SC(=O)NC1 VYYWZBLVFMZEPW-UHFFFAOYSA-N 0.000 claims description 4
- PJCYTIMTAXWZPH-UHFFFAOYSA-N 5-(4-methoxy-3-phenylmethoxyphenyl)-1,3-oxazolidin-2-one Chemical compound COC1=CC=C(C2OC(=O)NC2)C=C1OCC1=CC=CC=C1 PJCYTIMTAXWZPH-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- WSJBJAAZLUZIBN-UHFFFAOYSA-N 3-acetyl-5-(3,4-dimethoxyphenyl)-1,3-oxazolidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1OC(=O)N(C(C)=O)C1 WSJBJAAZLUZIBN-UHFFFAOYSA-N 0.000 claims description 3
- CIOXIFWTLJGCOD-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3-methyl-1,3-oxazolidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1OC(=O)N(C)C1 CIOXIFWTLJGCOD-UHFFFAOYSA-N 0.000 claims description 3
- FRZBUHRQAKOGNP-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-5-methyl-1,3-oxazolidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1(C)OC(=O)NC1 FRZBUHRQAKOGNP-UHFFFAOYSA-N 0.000 claims description 3
- BUBOFKLTSLHVCD-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-5-propyl-1,3-oxazolidin-2-one Chemical compound C=1C=C(OC)C(OC)=CC=1C1(CCC)CNC(=O)O1 BUBOFKLTSLHVCD-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 230000006181 N-acylation Effects 0.000 claims description 3
- 238000007126 N-alkylation reaction Methods 0.000 claims description 3
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- QIEFNVNAKZVPSU-UHFFFAOYSA-N 5-(3-cyclopentyloxy-4-methoxyphenyl)-1,3-oxazolidin-2-one Chemical compound COC1=CC=C(C2OC(=O)NC2)C=C1OC1CCCC1 QIEFNVNAKZVPSU-UHFFFAOYSA-N 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000008298 dragée Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- ROSHPNOENPPVQY-UHFFFAOYSA-N 3-benzyl-5-(3,4-dimethoxyphenyl)-1,3-oxazolidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1OC(=O)N(CC=2C=CC=CC=2)C1 ROSHPNOENPPVQY-UHFFFAOYSA-N 0.000 claims 1
- YIYDCUCQLSADHQ-UHFFFAOYSA-N 5-(3-butoxy-4-methoxyphenyl)-1,3-oxazolidin-2-one Chemical compound C1=C(OC)C(OCCCC)=CC(C2OC(=O)NC2)=C1 YIYDCUCQLSADHQ-UHFFFAOYSA-N 0.000 claims 1
- XCLCPJVQSUYSGK-UHFFFAOYSA-N 5-(3-cyclobutyloxy-4-methoxyphenyl)-1,3-oxazolidin-2-one Chemical compound COC1=CC=C(C2OC(=O)NC2)C=C1OC1CCC1 XCLCPJVQSUYSGK-UHFFFAOYSA-N 0.000 claims 1
- ZIGKKRHFLQXHMU-UHFFFAOYSA-N 5-(3-hydroxy-2-methoxyphenyl)-1,3-oxazolidin-2-one Chemical compound OC=1C(=C(C=CC1)C1CNC(O1)=O)OC ZIGKKRHFLQXHMU-UHFFFAOYSA-N 0.000 claims 1
- AAUZJBDBWKWMNN-UHFFFAOYSA-N 5-(4-cyclopentyloxy-3-methoxyphenyl)-1,3-oxazolidin-2-one Chemical compound COC1=CC(C2OC(=O)NC2)=CC=C1OC1CCCC1 AAUZJBDBWKWMNN-UHFFFAOYSA-N 0.000 claims 1
- QWYAJBQIHVEJNE-UHFFFAOYSA-N 5-(4-methoxy-3-phenoxyphenyl)-1,3-oxazolidin-2-one Chemical compound COC1=CC=C(C2OC(=O)NC2)C=C1OC1=CC=CC=C1 QWYAJBQIHVEJNE-UHFFFAOYSA-N 0.000 claims 1
- KYUUFCMVGWCGCK-UHFFFAOYSA-N 5-(4-methoxy-3-prop-2-ynoxyphenyl)-1,3-oxazolidin-2-one Chemical compound C1=C(OCC#C)C(OC)=CC=C1C1OC(=O)NC1 KYUUFCMVGWCGCK-UHFFFAOYSA-N 0.000 claims 1
- ZAIXAVYHWTYBDT-UHFFFAOYSA-N 5-[2-methoxy-3-(oxolan-3-yloxy)phenyl]-1,3-oxazolidin-2-one Chemical compound O1CC(CC1)OC=1C(=C(C=CC1)C1CNC(O1)=O)OC ZAIXAVYHWTYBDT-UHFFFAOYSA-N 0.000 claims 1
- YBAWCZVGJBFRHQ-UHFFFAOYSA-N 5-[4-methoxy-3-(2-methylpropoxy)phenyl]-1,3-oxazolidin-2-one Chemical compound C1=C(OCC(C)C)C(OC)=CC=C1C1OC(=O)NC1 YBAWCZVGJBFRHQ-UHFFFAOYSA-N 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 abstract description 7
- 125000001424 substituent group Chemical group 0.000 abstract description 5
- 201000010099 disease Diseases 0.000 abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract description 4
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 3
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract description 3
- 230000010261 cell growth Effects 0.000 abstract description 3
- 230000004060 metabolic process Effects 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 230000002082 anti-convulsion Effects 0.000 abstract description 2
- 230000001090 anti-dopaminergic effect Effects 0.000 abstract description 2
- 230000003502 anti-nociceptive effect Effects 0.000 abstract description 2
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 abstract description 2
- 229960001076 chlorpromazine Drugs 0.000 abstract description 2
- 229960003878 haloperidol Drugs 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 230000003463 hyperproliferative effect Effects 0.000 abstract description 2
- 239000012442 inert solvent Substances 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 230000000994 depressogenic effect Effects 0.000 abstract 1
- 239000003176 neuroleptic agent Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 50
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- 239000000203 mixture Substances 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000007717 exclusion Effects 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- JJBPZTLYONVMMO-UHFFFAOYSA-N 2-amino-1-(4-methoxy-3-phenylmethoxyphenyl)ethanol Chemical compound COC1=CC=C(C(O)CN)C=C1OCC1=CC=CC=C1 JJBPZTLYONVMMO-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- WIUFFBGZBFVVDL-UHFFFAOYSA-N 2-amino-1-(3,4-dimethoxyphenyl)ethanol Chemical compound COC1=CC=C(C(O)CN)C=C1OC WIUFFBGZBFVVDL-UHFFFAOYSA-N 0.000 description 4
- GPIDPQGNDCYNMV-UHFFFAOYSA-N 5-(3-hydroxy-4-methoxyphenyl)-1,3-oxazolidin-2-one Chemical compound C1=C(O)C(OC)=CC=C1C1OC(=O)NC1 GPIDPQGNDCYNMV-UHFFFAOYSA-N 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000008346 aqueous phase 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
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- DPYYYGAUCSEYLU-UHFFFAOYSA-N 1-amino-2-(3,4-dimethoxyphenyl)pentan-2-ol Chemical compound CCCC(O)(CN)C1=CC=C(OC)C(OC)=C1 DPYYYGAUCSEYLU-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- KZROGFITRJWKSR-UHFFFAOYSA-N 2-(3-cyclopentyloxy-4-methoxyphenyl)-2-hydroxyacetonitrile Chemical compound COC1=CC=C(C(O)C#N)C=C1OC1CCCC1 KZROGFITRJWKSR-UHFFFAOYSA-N 0.000 description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
- JTIPLNDENHDFNZ-UHFFFAOYSA-N 2-amino-1-(3,4-dimethoxyphenyl)propan-1-ol Chemical compound COC1=CC=C(C(O)C(C)N)C=C1OC JTIPLNDENHDFNZ-UHFFFAOYSA-N 0.000 description 2
- KGLGVBPFBKSBCX-UHFFFAOYSA-N 2-hydroxy-2-(4-methoxy-3-phenylmethoxyphenyl)acetonitrile Chemical compound COC1=CC=C(C(O)C#N)C=C1OCC1=CC=CC=C1 KGLGVBPFBKSBCX-UHFFFAOYSA-N 0.000 description 2
- VQVQZFHUXRSRBZ-UHFFFAOYSA-N 4-methoxy-3-phenylmethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1OCC1=CC=CC=C1 VQVQZFHUXRSRBZ-UHFFFAOYSA-N 0.000 description 2
- CVTIQQMSBKABFM-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-1,3-oxazolidine-2-thione Chemical compound C1=C(OC)C(OC)=CC=C1C1OC(=S)NC1 CVTIQQMSBKABFM-UHFFFAOYSA-N 0.000 description 2
- NDJGWGFOAAGHLD-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-4-methyl-1,3-oxazolidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C)NC(=O)O1 NDJGWGFOAAGHLD-UHFFFAOYSA-N 0.000 description 2
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- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000001730 monoaminergic effect Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 208000037244 polycythemia vera Diseases 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- 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
-
- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/16—Sulfur atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762655369 DE2655369A1 (de) | 1976-12-03 | 1976-12-03 | 5-(subst. phenyl)-oxazolidinone und deren schwefelanaloga sowie verfahren zu deren herstellung |
| DE19772745320 DE2745320A1 (de) | 1977-10-05 | 1977-10-05 | 5-(subst. phenyl)-oxazolidinone und deren schwefelanaloga sowie verfahren zu deren herstellung ii |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1588639A true GB1588639A (en) | 1981-04-29 |
Family
ID=25771221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB50350/77A Expired GB1588639A (en) | 1976-12-03 | 1977-12-02 | 5-(substituted phenyl)-oxazolidinones and sulphur analogues thereof and also a process for their production |
Country Status (19)
Cited By (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2923295A1 (de) * | 1978-06-09 | 1979-12-13 | Delalande Sa | Neue n-aryl-oxazolidinone, -oxazolidinthione, -pyrrolidinone, -pyrrolidine und -thiazolidinone, verfahren zu ihrer herstellung und solche verbindungen enthaltende arzneimittel |
| AU576448B2 (en) * | 1986-04-29 | 1988-08-25 | Pfizer Inc. | Calcium independent camp phosphodiesterase inhibitor antidepressant |
| EP0428313A3 (en) * | 1989-11-13 | 1991-11-06 | Pfizer Inc. | Pyrimidone derivatives and analogs in the treatment of asthma or certain skin disorders |
| US5414127A (en) * | 1988-01-19 | 1995-05-09 | Pfizer Inc. | Calcium independent camp phosphodiesterase inhibitor antidepressant |
| US5461056A (en) * | 1992-05-08 | 1995-10-24 | Pfizer Inc. | Pyrimidone derivatives and analogs in the treatment of asthma or certain skin disorders |
| US5491147A (en) * | 1992-10-23 | 1996-02-13 | Celltech, Limited | Tri-substituted phenyl derivatives and their use in pharmaceutical compositions and methods of treatment |
| US5580888A (en) * | 1992-12-23 | 1996-12-03 | Celltech Therapeutics Limited | Styryl derivatives as anti-inflammatory agents |
| US5608070A (en) * | 1993-12-22 | 1997-03-04 | Celltech Therapeutics Limited | Enantioselective process for the preparation of chiral triaryl derivatives and chiral intermediates for use therein |
| US5622977A (en) * | 1992-12-23 | 1997-04-22 | Celltech Therapeutics Limited | Tri-substituted (aryl or heteroaryl) derivatives and pharmaceutical compositions containing the same |
| US5633257A (en) * | 1993-03-10 | 1997-05-27 | Celltech Therapeutics Limited | Cyclo(alkyl and alkenyl)phenyl-alkenylyl(aryl and heteroaryl)compounds and pharmaceutical compositions containing them |
| US5693659A (en) * | 1994-06-23 | 1997-12-02 | Celltech Therapeutics Limited | Substituted oxime derivatives and processes for their preparation |
| US5739144A (en) * | 1993-03-10 | 1998-04-14 | Celltech Therapeutics Limited | Trisubstituted phenyl derivatives |
| US5780478A (en) * | 1994-06-22 | 1998-07-14 | Celltech Therapeutics, Limited | Tetra-substituted phenyl derivatives |
| US5780477A (en) * | 1994-06-22 | 1998-07-14 | Celltech Therapeutics, Limited | Trisubstituted phenyl derivatives and processes for their preparation |
| US5786354A (en) * | 1994-06-21 | 1998-07-28 | Celltech Therapeutics, Limited | Tri-substituted phenyl derivatives and processes for their preparation |
| US5798373A (en) * | 1995-12-21 | 1998-08-25 | Celltech Therapeutics, Limited | Tri-substituted phenyl derivatives useful as PDE IV inhibitors |
| US5849770A (en) * | 1995-12-21 | 1998-12-15 | Celltech Therapeutics Ltd. | Tri-substituted phenyl derivatives useful as PDE IV inhibitors |
| US5859034A (en) * | 1996-12-04 | 1999-01-12 | Celltech Therapeutics, Limited | Tri-substituted phenyl compounds which have useful pharmaceutical activity |
| US5866593A (en) * | 1993-12-22 | 1999-02-02 | Celltech Therapeutics Ltd. | Trisubstituted phenyl derivatives and processes for their preparation |
| US5922741A (en) * | 1996-04-24 | 1999-07-13 | Celltech Therapeutics Ltd. | 5-aminopyrazoles useful as tyrosine kinase inhibitors |
| US5958935A (en) * | 1995-11-20 | 1999-09-28 | Celltech Therapeutics Limited | Substituted 2-anilinopyrimidines useful as protein kinase inhibitors |
| US6048866A (en) * | 1997-03-14 | 2000-04-11 | Celltech Therapeutics, Limited | Substituted 2-anilinopryimidines useful as protein kinase inhibitors |
| US6057329A (en) * | 1996-12-23 | 2000-05-02 | Celltech Therapeutics Limited | Fused polycyclic 2-aminopyrimidine derivatives |
| US6093716A (en) * | 1996-09-16 | 2000-07-25 | Celltech Therapeutics, Limited | Substituted 2-pyrimidineamines and processes for their preparation |
| US6096747A (en) * | 1992-06-15 | 2000-08-01 | Celltech Therapeutics Limited | Phenylaminocarbonyl derivatives and processes for their preparation |
| US6114333A (en) * | 1996-10-28 | 2000-09-05 | Celltech Therapeutics Ltd. | 2-Pyrimidineamine derivatives and processes for their preparation |
| US6133257A (en) * | 1997-06-20 | 2000-10-17 | Celltech Therapeutics Limited | Fused polycyclic 2-aminopyrimidine derivatives |
| US6245774B1 (en) | 1994-06-21 | 2001-06-12 | Celltech Therapeutics Limited | Tri-substituted phenyl or pyridine derivatives |
| US6579983B1 (en) | 1999-06-18 | 2003-06-17 | Celltech R&D Limited | 5-cyano-2-aminopyrimidine derivatives |
| US6600037B1 (en) | 1999-10-20 | 2003-07-29 | Celltech R & D Limited | 4,5-disubstituted-2-aminopyrimidines |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2701215C2 (de) * | 1977-01-13 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Thiazolin-2-thionen |
| DE3438839A1 (de) * | 1984-10-19 | 1986-04-24 | Schering AG, 1000 Berlin und 4709 Bergkamen | Pharmazeutische praeparate |
| JPH01135098U (enrdf_load_stackoverflow) * | 1988-03-11 | 1989-09-14 |
-
1977
- 1977-11-28 SU SU772546252A patent/SU888821A3/ru active
- 1977-11-29 NL NL7713153A patent/NL7713153A/xx not_active Application Discontinuation
- 1977-12-01 DD DD7700202354A patent/DD133667A5/xx unknown
- 1977-12-01 LU LU78616A patent/LU78616A1/xx unknown
- 1977-12-01 SE SE7713635A patent/SE441446B/xx not_active IP Right Cessation
- 1977-12-01 IT IT30254/77A patent/IT1089341B/it active
- 1977-12-02 CH CH1477977A patent/CH635578A5/de not_active IP Right Cessation
- 1977-12-02 IL IL53520A patent/IL53520A/xx unknown
- 1977-12-02 IE IE2446/77A patent/IE46435B1/en not_active IP Right Cessation
- 1977-12-02 CA CA292,273A patent/CA1097657A/en not_active Expired
- 1977-12-02 GR GR54913A patent/GR64964B/el unknown
- 1977-12-02 DK DK536677A patent/DK149850C/da not_active IP Right Cessation
- 1977-12-02 GB GB50350/77A patent/GB1588639A/en not_active Expired
- 1977-12-02 JP JP14492277A patent/JPS5382777A/ja active Granted
- 1977-12-02 AU AU31175/77A patent/AU519994B2/en not_active Expired
- 1977-12-02 HU HU77SCHE632A patent/HU175676B/hu not_active IP Right Cessation
- 1977-12-05 AT AT868677A patent/AT357529B/de not_active IP Right Cessation
- 1977-12-05 FR FR7736525A patent/FR2372814A1/fr active Granted
- 1977-12-05 CS CS778086A patent/CS199694B2/cs unknown
Cited By (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2923295A1 (de) * | 1978-06-09 | 1979-12-13 | Delalande Sa | Neue n-aryl-oxazolidinone, -oxazolidinthione, -pyrrolidinone, -pyrrolidine und -thiazolidinone, verfahren zu ihrer herstellung und solche verbindungen enthaltende arzneimittel |
| AU576448B2 (en) * | 1986-04-29 | 1988-08-25 | Pfizer Inc. | Calcium independent camp phosphodiesterase inhibitor antidepressant |
| EP0247725A3 (en) * | 1986-04-29 | 1990-01-17 | Pfizer Inc. | Calcium independent camp phosphodiestrerase inhibitor antidepressant |
| US5414127A (en) * | 1988-01-19 | 1995-05-09 | Pfizer Inc. | Calcium independent camp phosphodiesterase inhibitor antidepressant |
| US5459145A (en) * | 1988-01-19 | 1995-10-17 | Pfizer Inc. | Calcium independent camp phosphodiesterase inhibitor antidepressant |
| EP0428313A3 (en) * | 1989-11-13 | 1991-11-06 | Pfizer Inc. | Pyrimidone derivatives and analogs in the treatment of asthma or certain skin disorders |
| US5342842A (en) * | 1989-11-13 | 1994-08-30 | Pfizer Inc. | Pyrimidone derivatives and analogs in the treatment of asthma or certain skin disorders |
| US5461056A (en) * | 1992-05-08 | 1995-10-24 | Pfizer Inc. | Pyrimidone derivatives and analogs in the treatment of asthma or certain skin disorders |
| US6096747A (en) * | 1992-06-15 | 2000-08-01 | Celltech Therapeutics Limited | Phenylaminocarbonyl derivatives and processes for their preparation |
| US5674880A (en) * | 1992-10-23 | 1997-10-07 | Celltech Therapeutics Limited | Tri-substituted phenyl derivatives and processes for their preparation |
| US5491147A (en) * | 1992-10-23 | 1996-02-13 | Celltech, Limited | Tri-substituted phenyl derivatives and their use in pharmaceutical compositions and methods of treatment |
| US6080790A (en) * | 1992-10-23 | 2000-06-27 | Celltech Therapeutics, Limited | Tri-substituted phenyl derivatives and processes for their preparations |
| US5622977A (en) * | 1992-12-23 | 1997-04-22 | Celltech Therapeutics Limited | Tri-substituted (aryl or heteroaryl) derivatives and pharmaceutical compositions containing the same |
| US5580888A (en) * | 1992-12-23 | 1996-12-03 | Celltech Therapeutics Limited | Styryl derivatives as anti-inflammatory agents |
| US5962483A (en) * | 1993-03-10 | 1999-10-05 | Celltech Therapeutics, Limited | Trisubstituted phenyl derivatives and processes for their preparation |
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Also Published As
| Publication number | Publication date |
|---|---|
| IE772446L (en) | 1978-06-03 |
| NL7713153A (nl) | 1978-06-06 |
| CS199694B2 (en) | 1980-07-31 |
| HU175676B (hu) | 1980-09-28 |
| CA1097657A (en) | 1981-03-17 |
| JPS5382777A (en) | 1978-07-21 |
| AU519994B2 (en) | 1982-01-07 |
| IL53520A0 (en) | 1978-03-10 |
| SE7713635L (sv) | 1978-06-04 |
| FR2372814B1 (enrdf_load_stackoverflow) | 1980-10-10 |
| CH635578A5 (en) | 1983-04-15 |
| DD133667A5 (de) | 1979-01-17 |
| AT357529B (de) | 1980-07-10 |
| LU78616A1 (enrdf_load_stackoverflow) | 1978-04-20 |
| IT1089341B (it) | 1985-06-18 |
| AU3117577A (en) | 1979-06-07 |
| SE441446B (sv) | 1985-10-07 |
| GR64964B (en) | 1980-06-10 |
| FR2372814A1 (fr) | 1978-06-30 |
| IE46435B1 (en) | 1983-06-15 |
| IL53520A (en) | 1981-07-31 |
| DK149850B (da) | 1986-10-13 |
| DK536677A (da) | 1978-06-04 |
| ATA868677A (de) | 1979-12-15 |
| SU888821A3 (ru) | 1981-12-07 |
| JPS6154792B2 (enrdf_load_stackoverflow) | 1986-11-25 |
| DK149850C (da) | 1987-04-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19921202 |