MXPA04007738A - 2-oxazolaminas y su uso como antagonistas del receptor 5-ht2b. - Google Patents
2-oxazolaminas y su uso como antagonistas del receptor 5-ht2b.Info
- Publication number
- MXPA04007738A MXPA04007738A MXPA04007738A MXPA04007738A MXPA04007738A MX PA04007738 A MXPA04007738 A MX PA04007738A MX PA04007738 A MXPA04007738 A MX PA04007738A MX PA04007738 A MXPA04007738 A MX PA04007738A MX PA04007738 A MXPA04007738 A MX PA04007738A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- group
- optionally substituted
- compound according
- amino
- Prior art date
Links
- 102000006969 5-HT2B Serotonin Receptor Human genes 0.000 title description 11
- 108010072584 5-HT2B Serotonin Receptor Proteins 0.000 title description 7
- ACTKAGSPIFDCMF-UHFFFAOYSA-N 1,3-oxazol-2-amine Chemical class NC1=NC=CO1 ACTKAGSPIFDCMF-UHFFFAOYSA-N 0.000 title description 3
- 229940044551 receptor antagonist Drugs 0.000 title description 3
- 239000002464 receptor antagonist Substances 0.000 title description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 119
- -1 aryl pyridine derivatives Chemical class 0.000 description 119
- 239000000203 mixture Substances 0.000 description 109
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 92
- 150000001875 compounds Chemical class 0.000 description 84
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 83
- 238000000034 method Methods 0.000 description 65
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
- 239000007787 solid Substances 0.000 description 60
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 56
- 238000003786 synthesis reaction Methods 0.000 description 56
- 230000015572 biosynthetic process Effects 0.000 description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- 125000000217 alkyl group Chemical group 0.000 description 46
- 239000000243 solution Substances 0.000 description 39
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 36
- 238000001819 mass spectrum Methods 0.000 description 36
- 101150041968 CDC13 gene Proteins 0.000 description 32
- 239000012267 brine Substances 0.000 description 32
- 229910052739 hydrogen Inorganic materials 0.000 description 32
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 32
- 230000002829 reductive effect Effects 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
- 229910052938 sodium sulfate Inorganic materials 0.000 description 28
- 235000011152 sodium sulphate Nutrition 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- 125000000623 heterocyclic group Chemical group 0.000 description 20
- 239000012044 organic layer Substances 0.000 description 20
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
- 238000004440 column chromatography Methods 0.000 description 19
- 150000003839 salts Chemical class 0.000 description 19
- 239000001257 hydrogen Substances 0.000 description 18
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- 235000019198 oils Nutrition 0.000 description 18
- 239000003208 petroleum Substances 0.000 description 18
- 125000003277 amino group Chemical group 0.000 description 17
- 125000004429 atom Chemical group 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- CFKWTZWWRBCTIQ-UHFFFAOYSA-N 4-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound O1C(N)=NC(C=2C3=CC=CC=C3C=CC=2)=C1 CFKWTZWWRBCTIQ-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000000524 functional group Chemical group 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- AWMZQHKHKGWNFG-UHFFFAOYSA-N 4-methyl-5-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound N1=C(N)OC(C=2C3=CC=CC=C3C=CC=2)=C1C AWMZQHKHKGWNFG-UHFFFAOYSA-N 0.000 description 12
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 12
- JGFDZZLUDWMUQH-UHFFFAOYSA-N Didecyldimethylammonium Chemical compound CCCCCCCCCC[N+](C)(C)CCCCCCCCCC JGFDZZLUDWMUQH-UHFFFAOYSA-N 0.000 description 12
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000012528 membrane Substances 0.000 description 12
- 239000001632 sodium acetate Substances 0.000 description 12
- 235000017281 sodium acetate Nutrition 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 230000027455 binding Effects 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 125000000753 cycloalkyl group Chemical group 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- 239000012453 solvate Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 239000007853 buffer solution Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 238000004452 microanalysis Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- CWCZGFGPXQWRIR-UHFFFAOYSA-N 4-(2-methylnaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound CC1=CC=C2C=CC=CC2=C1C1=COC(N)=N1 CWCZGFGPXQWRIR-UHFFFAOYSA-N 0.000 description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 8
- KFTUKCVZQBDUEY-UHFFFAOYSA-N 1-(2-methylnaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=C(C)C=CC2=C1 KFTUKCVZQBDUEY-UHFFFAOYSA-N 0.000 description 7
- 229940116892 5 Hydroxytryptamine 2B receptor antagonist Drugs 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 235000019502 Orange oil Nutrition 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 208000035475 disorder Diseases 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- VKNGBZDPBUPDGD-UHFFFAOYSA-N n-methyl-4-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound O1C(NC)=NC(C=2C3=CC=CC=C3C=CC=2)=C1 VKNGBZDPBUPDGD-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 239000010502 orange oil Substances 0.000 description 7
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 6
- JMAGAQLXBCJHHF-UHFFFAOYSA-N 1-(2-amino-1,3-oxazol-4-yl)naphthalen-2-ol Chemical compound O1C(N)=NC(C=2C3=CC=CC=C3C=CC=2O)=C1 JMAGAQLXBCJHHF-UHFFFAOYSA-N 0.000 description 6
- XPIBNCGHRJCREA-UHFFFAOYSA-N 1-(7-bromonaphthalen-1-yl)ethanone Chemical compound C1=C(Br)C=C2C(C(=O)C)=CC=CC2=C1 XPIBNCGHRJCREA-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 description 6
- SZKFDPNRGOMFLP-UHFFFAOYSA-N 5-methyl-4-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound O1C(N)=NC(C=2C3=CC=CC=C3C=CC=2)=C1C SZKFDPNRGOMFLP-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
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- 229910052799 carbon Inorganic materials 0.000 description 6
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000002287 radioligand Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
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- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 5
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- KXICJALOTGJZQL-UHFFFAOYSA-N 4-(1-benzothiophen-4-yl)-1,3-oxazol-2-amine Chemical compound O1C(N)=NC(C=2C=3C=CSC=3C=CC=2)=C1 KXICJALOTGJZQL-UHFFFAOYSA-N 0.000 description 5
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- UVTHUXIWXLDUPM-UHFFFAOYSA-N 4-(2-phenylmethoxynaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound O1C(N)=NC(C=2C3=CC=CC=C3C=CC=2OCC=2C=CC=CC=2)=C1 UVTHUXIWXLDUPM-UHFFFAOYSA-N 0.000 description 5
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- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 208000020685 sleep-wake disease Diseases 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- YYMWVZQRBNARFZ-UHFFFAOYSA-M sodium;2-[2,3-bis(sulfanyl)propoxy]ethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCOCC(S)CS YYMWVZQRBNARFZ-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 125000001010 sulfinic acid amide group Chemical group 0.000 description 1
- 150000003451 sulfinic acid amides Chemical class 0.000 description 1
- 150000003453 sulfinic acid esters Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000036263 tachygastria Effects 0.000 description 1
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 125000003666 tauryl group Chemical group [H]N([H])C([H])([H])C([H])([H])S(*)(=O)=O 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QMOMDADTIOMKJH-UHFFFAOYSA-N tert-butyl n-(5-methyl-4-oxo-1,3-oxazol-2-yl)carbamate Chemical compound CC1OC(NC(=O)OC(C)(C)C)=NC1=O QMOMDADTIOMKJH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- BQAJJINKFRRSFO-UHFFFAOYSA-N thiolane Chemical compound C1CCSC1.C1CCSC1 BQAJJINKFRRSFO-UHFFFAOYSA-N 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 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
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000004385 trihaloalkyl group Chemical group 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0203412.2A GB0203412D0 (en) | 2002-02-13 | 2002-02-13 | 5-HT 2B receptor antagonists |
| PCT/GB2003/000552 WO2003068226A1 (en) | 2002-02-13 | 2003-02-11 | 2-oxazolamines and their use as 5-ht2b receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA04007738A true MXPA04007738A (es) | 2004-10-15 |
Family
ID=9930999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA04007738A MXPA04007738A (es) | 2002-02-13 | 2003-02-11 | 2-oxazolaminas y su uso como antagonistas del receptor 5-ht2b. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7429607B2 (enExample) |
| EP (1) | EP1474140B1 (enExample) |
| JP (1) | JP4439266B2 (enExample) |
| KR (1) | KR20040084905A (enExample) |
| CN (1) | CN1633291A (enExample) |
| AU (1) | AU2003207297B2 (enExample) |
| CA (1) | CA2472762A1 (enExample) |
| DE (1) | DE60317632T2 (enExample) |
| EA (1) | EA200401077A1 (enExample) |
| GB (1) | GB0203412D0 (enExample) |
| IL (1) | IL163110A (enExample) |
| MX (1) | MXPA04007738A (enExample) |
| NO (1) | NO327465B1 (enExample) |
| NZ (1) | NZ534539A (enExample) |
| PL (1) | PL370221A1 (enExample) |
| WO (1) | WO2003068226A1 (enExample) |
| ZA (1) | ZA200406010B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1299948B1 (it) | 1998-04-02 | 2000-04-04 | Azionaria Costruzioni Acma Spa | Metodo e dispositivo per la formazione di gruppi di articoli appiattiti. |
| US20050176791A1 (en) * | 2002-02-13 | 2005-08-11 | Oxford Alexander W. | 5-HT2B receptor antagonists |
| JP2006528617A (ja) * | 2003-07-24 | 2006-12-21 | ファーマジーン ラボラトリーズ リミテッド | ５−ｈｔ２ｂ受容体アンタゴニスト |
| WO2005079845A1 (ja) | 2004-02-20 | 2005-09-01 | Astellas Pharma Inc. | 片頭痛予防薬 |
| SE0400850D0 (sv) * | 2004-03-30 | 2004-03-31 | Astrazeneca Ab | Novel Compounds |
| WO2005097113A2 (en) * | 2004-04-08 | 2005-10-20 | Pharmagene Laboratories Limited | 5-ht2b receptor antagonists |
| PL1797038T3 (pl) | 2004-09-29 | 2012-11-30 | Bayer Healthcare Llc | Termodynamicznie trwała postać tosylanu bay 43-9006 |
| WO2014085413A1 (en) * | 2012-11-28 | 2014-06-05 | Temple University - Of The Commonwealth System Of Higher Education | Disubstituted oxazolidin-2-ones 5-hydroxytryptamine receptor 2b activity modulators |
| KR101592068B1 (ko) | 2013-11-08 | 2016-02-05 | 순천향대학교 산학협력단 | 플라즈마 아포리포프로테인 h를 포함하는 아스피린 과민성 호흡계 질환 및 아스피린 내성 천식 구별 진단용 마커 및 구별 진단용 키트 |
| CN116789549A (zh) * | 2023-06-16 | 2023-09-22 | 山东科源化工有限公司 | 一种羟基乙酸乙烯酯的制备工艺 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0658559A1 (de) * | 1993-12-14 | 1995-06-21 | Chemisch Pharmazeutische Forschungsgesellschaft m.b.H. | Thienothiazinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als 5-dipoxygenase und Cyclooxygenaseinhibitoren |
| WO1995024200A1 (en) | 1994-03-11 | 1995-09-14 | Eli Lilly And Company | Method for treating 5ht2b receptor related conditions |
| US5663178A (en) | 1995-02-06 | 1997-09-02 | Eli Lilly And Company | Tetrahydro-beta carbolines |
| ATE227710T1 (de) * | 1996-04-03 | 2002-11-15 | Takeda Chemical Industries Ltd | Oxazole derivate,ihre herstellung und verwendung |
| US5958934A (en) | 1996-05-23 | 1999-09-28 | Syntex (U.S.A.) Inc. | Aryl pyrimidine derivatives and uses thereof |
| US5952331A (en) | 1996-05-23 | 1999-09-14 | Syntex (Usa) Inc. | Aryl pyrimidine derivatives |
| TW440563B (en) * | 1996-05-23 | 2001-06-16 | Hoffmann La Roche | Aryl pyrimidine derivatives and a pharmaceutical composition thereof |
| WO2000023444A1 (en) * | 1998-10-21 | 2000-04-27 | Abbott Laboratories | 5,7-disubstituted-4-aminopyrido[2,3-d]pyrimidine compounds |
| EP1200093B1 (en) | 1999-07-30 | 2003-09-24 | Pharmagene Laboratories Ltd | Use of 2-amino-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine in the treatment of gi disorders |
| AR035016A1 (es) * | 1999-08-25 | 2004-04-14 | Takeda Chemical Industries Ltd | Composicion de azol promotor de produccion/secrecion de neurotrofina, compuesto prodroga del mismo, composicion farmaceutica que lo comprende y uso del mismo para preparar esta ultima. |
-
2002
- 2002-02-13 GB GBGB0203412.2A patent/GB0203412D0/en not_active Ceased
-
2003
- 2003-02-11 DE DE60317632T patent/DE60317632T2/de not_active Expired - Lifetime
- 2003-02-11 WO PCT/GB2003/000552 patent/WO2003068226A1/en not_active Ceased
- 2003-02-11 NZ NZ534539A patent/NZ534539A/en not_active IP Right Cessation
- 2003-02-11 KR KR10-2004-7012479A patent/KR20040084905A/ko not_active Ceased
- 2003-02-11 CN CNA038039532A patent/CN1633291A/zh active Pending
- 2003-02-11 AU AU2003207297A patent/AU2003207297B2/en not_active Ceased
- 2003-02-11 PL PL03370221A patent/PL370221A1/xx not_active IP Right Cessation
- 2003-02-11 EP EP03704768A patent/EP1474140B1/en not_active Expired - Lifetime
- 2003-02-11 JP JP2003567408A patent/JP4439266B2/ja not_active Expired - Fee Related
- 2003-02-11 EA EA200401077A patent/EA200401077A1/ru unknown
- 2003-02-11 MX MXPA04007738A patent/MXPA04007738A/es active IP Right Grant
- 2003-02-11 CA CA002472762A patent/CA2472762A1/en not_active Abandoned
- 2003-02-12 US US10/364,672 patent/US7429607B2/en not_active Expired - Fee Related
-
2004
- 2004-07-20 IL IL163110A patent/IL163110A/en not_active IP Right Cessation
- 2004-07-28 ZA ZA200406010A patent/ZA200406010B/en unknown
- 2004-09-10 NO NO20043799A patent/NO327465B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200406010B (en) | 2005-06-08 |
| DE60317632D1 (de) | 2008-01-03 |
| JP2005528341A (ja) | 2005-09-22 |
| EP1474140A1 (en) | 2004-11-10 |
| US20040010022A1 (en) | 2004-01-15 |
| NZ534539A (en) | 2006-02-24 |
| US7429607B2 (en) | 2008-09-30 |
| NO327465B1 (no) | 2009-07-06 |
| EA200401077A1 (ru) | 2005-06-30 |
| KR20040084905A (ko) | 2004-10-06 |
| GB0203412D0 (en) | 2002-04-03 |
| WO2003068226A1 (en) | 2003-08-21 |
| CN1633291A (zh) | 2005-06-29 |
| EP1474140B1 (en) | 2007-11-21 |
| CA2472762A1 (en) | 2003-08-21 |
| IL163110A (en) | 2010-12-30 |
| AU2003207297A2 (en) | 2003-09-04 |
| JP4439266B2 (ja) | 2010-03-24 |
| DE60317632T2 (de) | 2008-10-30 |
| NO20043799L (no) | 2004-09-10 |
| AU2003207297A1 (en) | 2003-09-04 |
| AU2003207297B2 (en) | 2008-11-06 |
| PL370221A1 (en) | 2005-05-16 |
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