CS245091A3 - Oxime carbamates and oxime carbonates - Google Patents
Oxime carbamates and oxime carbonates Download PDFInfo
- Publication number
- CS245091A3 CS245091A3 CS912450A CS245091A CS245091A3 CS 245091 A3 CS245091 A3 CS 245091A3 CS 912450 A CS912450 A CS 912450A CS 245091 A CS245091 A CS 245091A CS 245091 A3 CS245091 A3 CS 245091A3
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- oxime
- mmol
- methoxyphenyl
- cyclopentyloxy
- ethanone
- Prior art date
Links
- -1 Oxime carbamates Chemical class 0.000 title claims abstract description 47
- 150000002923 oximes Chemical class 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 6
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000126 substance Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- HCUKYIRGHQRKMX-GORDUTHDSA-N [(E)-ethylideneamino] carbamate Chemical compound NC(=O)O\N=C\C HCUKYIRGHQRKMX-GORDUTHDSA-N 0.000 claims description 3
- ZWOZSAMZVNWWQU-PTGBLXJZSA-N [(e)-[1-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethylidene]amino] carbamate Chemical compound COC1=CC=C(C(\CC=2C=CC=CC=2)=N\OC(N)=O)C=C1OC1CCCC1 ZWOZSAMZVNWWQU-PTGBLXJZSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- DSQKSRRBROSJAB-GZTJUZNOSA-N [(e)-1-(3-butoxy-4-methoxyphenyl)ethylideneamino] n-methylcarbamate Chemical compound CCCCOC1=CC(C(\C)=N\OC(=O)NC)=CC=C1OC DSQKSRRBROSJAB-GZTJUZNOSA-N 0.000 claims description 2
- HMDJBMPIIVFEGX-GZTJUZNOSA-N [(e)-1-(3-cyclopentyloxy-4-methoxyphenyl)ethylideneamino] methyl carbonate Chemical compound COC(=O)O\N=C(/C)C1=CC=C(OC)C(OC2CCCC2)=C1 HMDJBMPIIVFEGX-GZTJUZNOSA-N 0.000 claims description 2
- VMYYZWAHSZFBMJ-WOJGMQOQSA-N [(e)-1-(3-cyclopentyloxy-4-methoxyphenyl)ethylideneamino] n-methylcarbamate Chemical compound CNC(=O)O\N=C(/C)C1=CC=C(OC)C(OC2CCCC2)=C1 VMYYZWAHSZFBMJ-WOJGMQOQSA-N 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- WCLVAXSAYPDJRR-RCCKNPSSSA-N [(e)-1-(3-butoxy-4-methoxyphenyl)ethylideneamino] phenyl carbonate Chemical compound C1=C(OC)C(OCCCC)=CC(C(\C)=N\OC(=O)OC=2C=CC=CC=2)=C1 WCLVAXSAYPDJRR-RCCKNPSSSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 29
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 19
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 19
- 150000002576 ketones Chemical class 0.000 abstract description 8
- 208000006673 asthma Diseases 0.000 abstract description 7
- 230000001154 acute effect Effects 0.000 abstract description 4
- 210000001519 tissue Anatomy 0.000 abstract description 4
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 229940095074 cyclic amp Drugs 0.000 abstract description 3
- 210000004969 inflammatory cell Anatomy 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 210000002460 smooth muscle Anatomy 0.000 abstract description 3
- 230000003182 bronchodilatating effect Effects 0.000 abstract description 2
- 230000001684 chronic effect Effects 0.000 abstract description 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 108010044467 Isoenzymes Proteins 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 230000007170 pathology Effects 0.000 abstract 1
- 230000002685 pulmonary effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 192
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 49
- 239000000243 solution Substances 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 239000007787 solid Substances 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- 238000005481 NMR spectroscopy Methods 0.000 description 30
- 238000000034 method Methods 0.000 description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000377 silicon dioxide Substances 0.000 description 15
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 238000003818 flash chromatography Methods 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- FZFWPURYSWKIRT-UHFFFAOYSA-N 3-cyclopentyloxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1OC1CCCC1 FZFWPURYSWKIRT-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 5
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- STUPRJVKLDILNL-UHFFFAOYSA-N 1-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethanone Chemical compound COC1=CC=C(C(=O)CC=2C=CC=CC=2)C=C1OC1CCCC1 STUPRJVKLDILNL-UHFFFAOYSA-N 0.000 description 2
- HAMGEWVZNNUJDP-UHFFFAOYSA-N 1-(3-cyclopentyloxy-4-methoxyphenyl)-3-methylbutan-1-ol Chemical compound COC1=CC=C(C(O)CC(C)C)C=C1OC1CCCC1 HAMGEWVZNNUJDP-UHFFFAOYSA-N 0.000 description 2
- FTTIPUJGCXGZIZ-UHFFFAOYSA-N 1-(3-cyclopentyloxy-4-methoxyphenyl)-3-methylbutan-2-one Chemical compound COC1=CC=C(CC(=O)C(C)C)C=C1OC1CCCC1 FTTIPUJGCXGZIZ-UHFFFAOYSA-N 0.000 description 2
- BFQYBNXJQBXNSS-UHFFFAOYSA-N 1-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenylpropan-2-one Chemical compound C1=C(OC2CCCC2)C(OC)=CC=C1CC(=O)CC1=CC=CC=C1 BFQYBNXJQBXNSS-UHFFFAOYSA-N 0.000 description 2
- JKLSPSUHPACCOS-UHFFFAOYSA-N 1-(3-cyclopentyloxy-4-methoxyphenyl)ethanol Chemical compound COC1=CC=C(C(C)O)C=C1OC1CCCC1 JKLSPSUHPACCOS-UHFFFAOYSA-N 0.000 description 2
- CSSRHTDXZIBTMI-UHFFFAOYSA-N 3-butoxy-4-methoxybenzaldehyde Chemical compound CCCCOC1=CC(C=O)=CC=C1OC CSSRHTDXZIBTMI-UHFFFAOYSA-N 0.000 description 2
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 2
- YDTVMCUQTXRULU-UHFFFAOYSA-N 4-methoxy-3-(3-phenoxypropoxy)benzaldehyde Chemical compound COC1=CC=C(C=O)C=C1OCCCOC1=CC=CC=C1 YDTVMCUQTXRULU-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
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- 229940124630 bronchodilator Drugs 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
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- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
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- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- 241000282465 Canis Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
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- RCZFHCGWAPQINU-VXLYETTFSA-N [(e)-1-[3-(3-bicyclo[2.2.1]heptanyloxy)-4-methoxyphenyl]ethylideneamino] carbamate Chemical compound COC1=CC=C(C(\C)=N\OC(N)=O)C=C1OC1C(C2)CCC2C1 RCZFHCGWAPQINU-VXLYETTFSA-N 0.000 description 1
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- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 229940110456 cocoa butter Drugs 0.000 description 1
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- 235000019425 dextrin Nutrition 0.000 description 1
- DAKIDYQCFJQMDF-UHFFFAOYSA-N dichloromethane;pyridine Chemical compound ClCCl.C1=CC=NC=C1 DAKIDYQCFJQMDF-UHFFFAOYSA-N 0.000 description 1
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- STTRYQAGHGJXJJ-LICLKQGHSA-N filaminast Chemical compound COC1=CC=C(C(\C)=N\OC(N)=O)C=C1OC1CCCC1 STTRYQAGHGJXJJ-LICLKQGHSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
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- RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 description 1
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- YSMZEMQBSONIMJ-UHFFFAOYSA-M magnesium;2-methanidylpropane;chloride Chemical compound [Mg+2].[Cl-].CC(C)[CH2-] YSMZEMQBSONIMJ-UHFFFAOYSA-M 0.000 description 1
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- JJJGROIGPJBFRR-UHFFFAOYSA-N n-[1-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethylidene]hydroxylamine Chemical compound COC1=CC=C(C(CC=2C=CC=CC=2)=NO)C=C1OC1CCCC1 JJJGROIGPJBFRR-UHFFFAOYSA-N 0.000 description 1
- DUWKIBVDLOHLBT-UHFFFAOYSA-N n-[1-(3-cyclopentyloxy-4-methoxyphenyl)-3-methylbutan-2-ylidene]hydroxylamine Chemical compound COC1=CC=C(CC(=NO)C(C)C)C=C1OC1CCCC1 DUWKIBVDLOHLBT-UHFFFAOYSA-N 0.000 description 1
- MQYYZLUXDUEHCC-UHFFFAOYSA-N n-[1-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenylpropan-2-ylidene]hydroxylamine Chemical compound C1=C(OC2CCCC2)C(OC)=CC=C1CC(=NO)CC1=CC=CC=C1 MQYYZLUXDUEHCC-UHFFFAOYSA-N 0.000 description 1
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- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
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- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
- 229950005741 rolipram Drugs 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
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- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
-
- 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
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Polyesters Or Polycarbonates (AREA)
- Reinforced Plastic Materials (AREA)
- Quinoline Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/564,263 US5124455A (en) | 1990-08-08 | 1990-08-08 | Oxime-carbamates and oxime-carbonates as bronchodilators and anti-inflammatory agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS245091A3 true CS245091A3 (en) | 1992-03-18 |
Family
ID=24253782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS912450A CS245091A3 (en) | 1990-08-08 | 1991-08-07 | Oxime carbamates and oxime carbonates |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5124455A (de) |
| EP (1) | EP0470805B1 (de) |
| JP (1) | JP2651292B2 (de) |
| KR (1) | KR920004335A (de) |
| CN (1) | CN1029613C (de) |
| AT (1) | ATE111076T1 (de) |
| AU (1) | AU640251B2 (de) |
| CA (1) | CA2048518A1 (de) |
| CS (1) | CS245091A3 (de) |
| CY (1) | CY2057B1 (de) |
| DE (1) | DE69103846T2 (de) |
| DK (1) | DK0470805T3 (de) |
| ES (1) | ES2060307T3 (de) |
| FI (1) | FI913738A7 (de) |
| GB (1) | GB2246777B (de) |
| HU (3) | HU207289B (de) |
| IE (1) | IE66049B1 (de) |
| IL (1) | IL99081A (de) |
| MX (1) | MX9100549A (de) |
| NO (1) | NO174805B (de) |
| NZ (1) | NZ239279A (de) |
| PT (1) | PT98596B (de) |
| RU (1) | RU2051145C1 (de) |
| ZA (1) | ZA916154B (de) |
Families Citing this family (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5430176A (en) * | 1990-07-06 | 1995-07-04 | The Upjohn Company | Intermediate used for the preparation of deferoxamine |
| US5698711A (en) | 1991-01-28 | 1997-12-16 | Rhone-Poulenc Rorer Limited | Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic- or heteroatom-containing linking group |
| GB9311281D0 (en) * | 1993-06-01 | 1993-07-21 | Rhone Poulenc Rorer Ltd | Novel composition of matter |
| GB9204808D0 (en) * | 1992-03-04 | 1992-04-15 | Rhone Poulenc Rorer Ltd | Novel compositions of matter |
| GB9212673D0 (en) * | 1992-06-15 | 1992-07-29 | Celltech Ltd | Chemical compounds |
| CZ14795A3 (en) * | 1992-07-28 | 1996-07-17 | Rhone Poulenc Rorer Ltd | Benzene derivative containing phenyl group bound to aryl or heteroaryl fraction through an aliphatic or hetero atom containing group, process of its preparation and pharmaceutical composition containing thereof |
| US5679696A (en) * | 1992-07-28 | 1997-10-21 | Rhone-Poulenc Rorer Limited | Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic-or heteroatom-containing linking group |
| GB9222253D0 (en) * | 1992-10-23 | 1992-12-09 | Celltech Ltd | Chemical compounds |
| US5622977A (en) * | 1992-12-23 | 1997-04-22 | Celltech Therapeutics Limited | Tri-substituted (aryl or heteroaryl) derivatives and pharmaceutical compositions containing the same |
| GB9226830D0 (en) * | 1992-12-23 | 1993-02-17 | Celltech Ltd | Chemical compounds |
| GB9304920D0 (en) * | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| GB9304919D0 (en) * | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| GB9312853D0 (en) | 1993-06-22 | 1993-08-04 | Euro Celtique Sa | Chemical compounds |
| US5665754A (en) * | 1993-09-20 | 1997-09-09 | Glaxo Wellcome Inc. | Substituted pyrrolidines |
| US5502072A (en) * | 1993-11-26 | 1996-03-26 | Pfizer Inc. | Substituted oxindoles |
| GB9326173D0 (en) * | 1993-12-22 | 1994-02-23 | Celltech Ltd | Chemical compounds and process |
| EP0738268B1 (de) * | 1993-12-22 | 2004-03-03 | Celltech R&D Limited | Trisubstituierte phenyl-derivate, verfahren zu deren herstellung und deren verwendung als phosphodiesterase (typ iv) hemmstoffe |
| US5786354A (en) * | 1994-06-21 | 1998-07-28 | Celltech Therapeutics, Limited | Tri-substituted phenyl derivatives and processes for their preparation |
| US6245774B1 (en) | 1994-06-21 | 2001-06-12 | Celltech Therapeutics Limited | Tri-substituted phenyl or pyridine derivatives |
| GB9412571D0 (en) | 1994-06-22 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| GB9412573D0 (en) * | 1994-06-22 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| GB9412672D0 (en) * | 1994-06-23 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| US5591776A (en) * | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
| US5922751A (en) | 1994-06-24 | 1999-07-13 | Euro-Celtique, S.A. | Aryl pyrazole compound for inhibiting phosphodiesterase IV and methods of using same |
| US6514949B1 (en) | 1994-07-11 | 2003-02-04 | University Of Virginia Patent Foundation | Method compositions for treating the inflammatory response |
| US6448235B1 (en) | 1994-07-11 | 2002-09-10 | University Of Virginia Patent Foundation | Method for treating restenosis with A2A adenosine receptor agonists |
| US5665737B1 (en) * | 1994-10-12 | 1999-02-16 | Euro Celtique Sa | Substituted benzoxazoles |
| US6025361A (en) * | 1994-12-13 | 2000-02-15 | Euro-Celtique, S.A. | Trisubstituted thioxanthines |
| DE69531506T2 (de) | 1994-12-13 | 2004-06-24 | Euroceltique S.A. | Arylthioxanthine |
| US6268373B1 (en) | 1995-06-07 | 2001-07-31 | Euro-Celtique S.A. | Trisubstituted thioxanthines |
| CA2227237C (en) | 1995-07-26 | 2005-12-13 | Pfizer Inc. | N-(aroyl)glycine hydroxamic acid derivatives and related compounds |
| GB9523675D0 (en) * | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9526245D0 (en) * | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9526243D0 (en) * | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9526246D0 (en) * | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| US6075016A (en) | 1996-04-10 | 2000-06-13 | Euro-Celtique S.A. | 6,5-fused aromatic ring systems having enhanced phosphodiesterase IV inhibitory activity |
| GB9608435D0 (en) * | 1996-04-24 | 1996-06-26 | Celltech Therapeutics Ltd | Chemical compounds |
| US5864037A (en) | 1996-06-06 | 1999-01-26 | Euro-Celtique, S.A. | Methods for the synthesis of chemical compounds having PDE-IV inhibitory activity |
| JP4373497B2 (ja) | 1996-06-19 | 2009-11-25 | ローン−プーラン・ロレ・リミテツド | 置換されたアザビシクロ化合物、ならびにｔｎｆおよびサイクリックａｍｐホスホジエステラーゼ産生の阻害剤としてのそれらの使用 |
| GB9619284D0 (en) * | 1996-09-16 | 1996-10-30 | Celltech Therapeutics Ltd | Chemical compounds |
| US5744473A (en) * | 1996-09-16 | 1998-04-28 | Euro-Celtique, S.A. | PDE IV inhibitors: "bis-compounds" |
| GB9622363D0 (en) | 1996-10-28 | 1997-01-08 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9625184D0 (en) * | 1996-12-04 | 1997-01-22 | Celltech Therapeutics Ltd | Chemical compounds |
| EP0946523A1 (de) | 1996-12-23 | 1999-10-06 | Celltech Therapeutics Limited | Kondensierte polycyclische 2-aminopyrimidinderivate, ihre herstellung und verwendung als proteininhibitoren von tyrosinkinase |
| US5981549A (en) * | 1997-02-14 | 1999-11-09 | Synapse Pharmaceutical International | Method for controlling or alleviating the symptoms of respiratory disease and allergies |
| GB9705361D0 (en) | 1997-03-14 | 1997-04-30 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9713087D0 (en) * | 1997-06-20 | 1997-08-27 | Celltech Therapeutics Ltd | Chemical compounds |
| CN1130363C (zh) | 1997-11-12 | 2003-12-10 | 三菱化学株式会社 | 嘌呤衍生物以及含有其作为有效成分的药物 |
| US6117878A (en) * | 1998-02-24 | 2000-09-12 | University Of Virginia | 8-phenyl- or 8-cycloalkyl xanthine antagonists of A2B human adenosine receptors |
| KR100479019B1 (ko) * | 1998-05-22 | 2005-08-29 | 씨제이 주식회사 | 캐테콜히드라존유도체,이의제조방법및그를함유한약제학적조성물 |
| KR100578425B1 (ko) * | 1998-10-16 | 2007-01-11 | 씨제이 주식회사 | 캐테콜 히드라진 유도체, 이의 제조 방법 및 이를 함유한 약제학적 조성물 |
| US6232297B1 (en) | 1999-02-01 | 2001-05-15 | University Of Virginia Patent Foundation | Methods and compositions for treating inflammatory response |
| US7378400B2 (en) * | 1999-02-01 | 2008-05-27 | University Of Virginia Patent Foundation | Method to reduce an inflammatory response from arthritis |
| US7427606B2 (en) * | 1999-02-01 | 2008-09-23 | University Of Virginia Patent Foundation | Method to reduce inflammatory response in transplanted tissue |
| WO2000068231A1 (en) * | 1999-05-11 | 2000-11-16 | Mitsubishi Chemical Corporation | Purine derivative dihydrate, drugs containing the same as the active ingredient and intermediate in the production thereof |
| GB9914258D0 (en) | 1999-06-18 | 1999-08-18 | Celltech Therapeutics Ltd | Chemical compounds |
| US6322771B1 (en) | 1999-06-18 | 2001-11-27 | University Of Virginia Patent Foundation | Induction of pharmacological stress with adenosine receptor agonists |
| CA2715683A1 (en) | 1999-08-21 | 2001-03-01 | Nycomed Gmbh | Synergistic combination |
| GB9924862D0 (en) | 1999-10-20 | 1999-12-22 | Celltech Therapeutics Ltd | Chemical compounds |
| CA2402384A1 (en) * | 2000-03-16 | 2001-09-20 | Inflazyme Pharmaceuticals Ltd. | Benzylated pde4 inhibitors |
| BR0209774A (pt) * | 2001-05-29 | 2004-06-01 | Schering Ag | Pirimidinas inibidoras de cdk, sua preparação e aplicação como medicamento |
| AU2002322720B2 (en) | 2001-07-25 | 2008-11-13 | Raptor Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| NZ556354A (en) * | 2001-10-01 | 2008-10-31 | Univ Virginia | 2-Propynyl adenosine analogs having A2A agonist activity and compositions thereof |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US7153824B2 (en) | 2003-04-01 | 2006-12-26 | Applied Research Systems Ars Holding N.V. | Inhibitors of phosphodiesterases in infertility |
| FR2861069B1 (fr) * | 2003-10-17 | 2005-12-09 | Galderma Res & Dev | NOUVEAUX LIGANDS ACTIVATEURS DES RECEPTEURS RARs, UTILISATION EN MEDECINE HUMAINE AINSI QU'EN COSMETIQUE |
| US7122705B2 (en) * | 2004-04-08 | 2006-10-17 | Wyeth | Method for preparing 3-cyclopentyloxy-4-methoxybenzaldehyde |
| ATE413398T1 (de) * | 2004-04-08 | 2008-11-15 | Wyeth Corp | Thioamidderivate als progesteronrezeptormodulatoren |
| US7576069B2 (en) * | 2004-08-02 | 2009-08-18 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having A2A agonist activity |
| WO2006023272A1 (en) * | 2004-08-02 | 2006-03-02 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having a2a agonist activity |
| AU2005267706B2 (en) * | 2004-08-02 | 2011-12-08 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs with modified 5'-ribose groups having A2A agonist activity |
| CA2789262C (en) | 2005-04-28 | 2016-10-04 | Proteus Digital Health, Inc. | Pharma-informatics system |
| JP2009514969A (ja) | 2005-11-09 | 2009-04-09 | コンビナトアールエックス インコーポレーティッド | 医学的状態を治療するための方法、組成物、およびキット |
| US8178509B2 (en) * | 2006-02-10 | 2012-05-15 | University Of Virginia Patent Foundation | Method to treat sickle cell disease |
| US8188063B2 (en) * | 2006-06-19 | 2012-05-29 | University Of Virginia Patent Foundation | Use of adenosine A2A modulators to treat spinal cord injury |
| EP2063905B1 (de) | 2006-09-18 | 2014-07-30 | Raptor Pharmaceutical Inc | Behandlungen von lebererkrankungen durch verabreichung von konjugaten aus rezeptor-assoziierten proteinen |
| MX354786B (es) | 2007-06-04 | 2018-03-21 | Synergy Pharmaceuticals Inc | Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos. |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| EP2022783A1 (de) | 2007-08-08 | 2009-02-11 | CHIESI FARMACEUTICI S.p.A. | 1-Phenyl-2-Pyridinylalkyl-Alkoholderivate als Phosphodiesterasehemmer |
| US8058259B2 (en) * | 2007-12-20 | 2011-11-15 | University Of Virginia Patent Foundation | Substituted 4-{3-[6-amino-9-(3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid esters as A2AR agonists |
| ES2522968T3 (es) | 2008-06-04 | 2014-11-19 | Synergy Pharmaceuticals Inc. | Agonistas de guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| AU2009270833B2 (en) | 2008-07-16 | 2015-02-19 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| TR201908314T4 (tr) | 2009-02-20 | 2019-06-21 | 2 Bbb Medicines B V | Glutatyon bazlı ilaç dağıtım sistemi. |
| KR101909711B1 (ko) | 2009-05-06 | 2018-12-19 | 라보라토리 스킨 케어, 인크. | 활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법 |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
| DK2681236T3 (en) | 2011-03-01 | 2018-04-16 | Synergy Pharmaceuticals Inc | PROCEDURE FOR MANUFACTURING GUANYLATE CYCLASE-C-AGONISTS |
| WO2014131024A2 (en) | 2013-02-25 | 2014-08-28 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| AU2014235215A1 (en) | 2013-03-15 | 2015-10-01 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| BR112015030326A2 (pt) | 2013-06-05 | 2017-08-29 | Synergy Pharmaceuticals Inc | Agonistas ultrapuros de guanilato ciclase c, método de fabricar e usar os mesmos |
| AU2014305843B2 (en) | 2013-08-09 | 2019-08-29 | Ardelyx, Inc. | Compounds and methods for inhibiting phosphate transport |
| CN106146350B (zh) * | 2016-07-21 | 2017-10-20 | 华南理工大学 | 一种合成氨基甲酸肟酯衍生物的新方法 |
| EP4706758A3 (de) | 2019-05-21 | 2026-05-06 | Ardelyx, Inc. | Verfahren zur hemmung des phosphattransports |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3466316A (en) * | 1964-09-23 | 1969-09-09 | Union Carbide Corp | Alpha-cyano carbamoyloxime compounds |
| FR1575544A (de) * | 1967-11-09 | 1969-07-25 | ||
| US3923833A (en) * | 1968-05-01 | 1975-12-02 | Hoffmann La Roche | N-{8 (1-cyano-2-phenyl)ethyl{9 carbamates |
| US3647861A (en) * | 1970-08-25 | 1972-03-07 | Du Pont | Substituted o-carbamylhydroxamates |
| DE2111156C3 (de) * | 1971-03-09 | 1975-11-06 | Hoechst Ag, 6000 Frankfurt | Oximcarbamatverbindungen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende insektizide Mittel |
| FR2201885A1 (en) * | 1972-10-10 | 1974-05-03 | Delalande Sa | 4-Aryl carbonyl methyl pyrimidine oxime carbamates - prepd. by treatment of the oxime with an isocyanate, used as sedatives, analgesics, vasodilators, diuretics |
| FR2202689B1 (de) * | 1972-10-17 | 1975-10-31 | Delalande Sa | |
| FR2204406A1 (en) * | 1972-10-26 | 1974-05-24 | Delalande Sa | 1-Phenyl-3-aminocarbonylpropan-1-one oxime carbamates - with analgesic, antiinflammatory, hypotensive and sedative activities etc. |
| FR2244499A1 (en) * | 1973-06-07 | 1975-04-18 | Delalande Sa | Indol-3-ylformaldoxime carbamates - for treating anxiety epilepsy, cardiac arrhythmias, asthma, intestinal spasm, peptic ulcer, cardiac insufficiency |
| DE2655369A1 (de) * | 1976-12-03 | 1978-06-08 | Schering Ag | 5-(subst. phenyl)-oxazolidinone und deren schwefelanaloga sowie verfahren zu deren herstellung |
| HU179019B (en) * | 1978-11-01 | 1982-08-28 | Gyogyszekutato Intezet | Process for preparing 4-//3,4-dialkoxy-phenyl/-alkyl/- 2imidazolidinone derivatives |
| US4475945A (en) * | 1980-01-14 | 1984-10-09 | Ciba-Geigy Corporation | Aminoglyoxyloitrile oximino carboxylic acid esters and thio esters for the protection of crops against injury by herbicides |
| DE3438839A1 (de) * | 1984-10-19 | 1986-04-24 | Schering AG, 1000 Berlin und 4709 Bergkamen | Pharmazeutische praeparate |
| EP0186817B1 (de) * | 1984-12-10 | 1989-08-02 | Nissan Chemical Industries Ltd. | 3(2H)Pyridazinon, Verfahren zu seiner Herstellung und dieses enthaltendes anti-allergisches Mittel |
| FI875724A0 (fi) * | 1986-04-29 | 1987-12-28 | Pfizer | Av kalcium oberoende camp fosfodiesteras-inhibitordepressant. |
| GB8711802D0 (en) * | 1987-05-19 | 1987-06-24 | Fujisawa Pharmaceutical Co | Dithioacetal compounds |
| RU2104306C1 (ru) * | 1989-11-13 | 1998-02-10 | Пфайзер Инк. | Способ получения оптически активного (2s)- или (2r)-эндо-бицикло[2.2.1]гептан-2-ола, способ получения 5-(3-[(2r)-экзо-бицикло[2.2.1]гепт-2-илокси]-4-метоксифенил)-3,4,5,6-тетрагидропиримидин-2(1н)-она, оптически активный 5-(3-[экзо-бицикло[2.2.1]гепт-2-илокси]4-метоксифенил)-3,4,5,6-тетрагидропиримидин-2(1н)-он, оптически активные промежуточные соединения и способ их получения |
-
1990
- 1990-08-08 US US07/564,263 patent/US5124455A/en not_active Expired - Fee Related
-
1991
- 1991-08-05 JP JP3195183A patent/JP2651292B2/ja not_active Expired - Lifetime
- 1991-08-05 ZA ZA916154A patent/ZA916154B/xx unknown
- 1991-08-05 IL IL9908191A patent/IL99081A/en unknown
- 1991-08-05 AU AU81623/91A patent/AU640251B2/en not_active Ceased
- 1991-08-06 FI FI913738A patent/FI913738A7/fi unknown
- 1991-08-06 KR KR1019910013552A patent/KR920004335A/ko not_active Abandoned
- 1991-08-06 DK DK91307197.3T patent/DK0470805T3/da active
- 1991-08-06 NZ NZ239279A patent/NZ239279A/xx unknown
- 1991-08-06 DE DE69103846T patent/DE69103846T2/de not_active Expired - Fee Related
- 1991-08-06 MX MX9100549A patent/MX9100549A/es unknown
- 1991-08-06 GB GB9116950A patent/GB2246777B/en not_active Expired - Fee Related
- 1991-08-06 ES ES91307197T patent/ES2060307T3/es not_active Expired - Lifetime
- 1991-08-06 AT AT91307197T patent/ATE111076T1/de active
- 1991-08-06 EP EP91307197A patent/EP0470805B1/de not_active Expired - Lifetime
- 1991-08-07 HU HU912634A patent/HU207289B/hu not_active IP Right Cessation
- 1991-08-07 HU HU9202417A patent/HU215159B/hu not_active IP Right Cessation
- 1991-08-07 RU SU915001278A patent/RU2051145C1/ru active
- 1991-08-07 NO NO913065A patent/NO174805B/no unknown
- 1991-08-07 IE IE279491A patent/IE66049B1/en not_active IP Right Cessation
- 1991-08-07 CA CA002048518A patent/CA2048518A1/en not_active Abandoned
- 1991-08-07 CN CN91105530A patent/CN1029613C/zh not_active Expired - Fee Related
- 1991-08-07 PT PT98596A patent/PT98596B/pt not_active IP Right Cessation
- 1991-08-07 CS CS912450A patent/CS245091A3/cs unknown
-
1995
- 1995-06-28 HU HU95P/P00483P patent/HU211643A9/hu unknown
-
1998
- 1998-04-30 CY CY9802057A patent/CY2057B1/xx unknown
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