NO327465B1 - 2-oksasolaminer og deres anvendelse samt farmasoytisk sammensetning - Google Patents
2-oksasolaminer og deres anvendelse samt farmasoytisk sammensetning Download PDFInfo
- Publication number
- NO327465B1 NO327465B1 NO20043799A NO20043799A NO327465B1 NO 327465 B1 NO327465 B1 NO 327465B1 NO 20043799 A NO20043799 A NO 20043799A NO 20043799 A NO20043799 A NO 20043799A NO 327465 B1 NO327465 B1 NO 327465B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- optionally substituted
- hydroxy
- alkoxy
- cycloalkyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- ACTKAGSPIFDCMF-UHFFFAOYSA-N 1,3-oxazol-2-amine Chemical class NC1=NC=CO1 ACTKAGSPIFDCMF-UHFFFAOYSA-N 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 124
- 150000001875 compounds Chemical class 0.000 claims description 107
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 79
- 238000000034 method Methods 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical group 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 208000035475 disorder Diseases 0.000 claims description 24
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000003368 amide group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 16
- 125000001544 thienyl group Chemical group 0.000 claims description 16
- 125000004423 acyloxy group Chemical group 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 102000006969 5-HT2B Serotonin Receptor Human genes 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 108010072584 5-HT2B Serotonin Receptor Proteins 0.000 claims description 9
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 208000007848 Alcoholism Diseases 0.000 claims description 7
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 7
- 206010069632 Bladder dysfunction Diseases 0.000 claims description 7
- 206010013935 Dysmenorrhoea Diseases 0.000 claims description 7
- 201000009273 Endometriosis Diseases 0.000 claims description 7
- 206010016654 Fibrosis Diseases 0.000 claims description 7
- 206010020772 Hypertension Diseases 0.000 claims description 7
- 206010021639 Incontinence Diseases 0.000 claims description 7
- 208000019695 Migraine disease Diseases 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 7
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 7
- 201000007930 alcohol dependence Diseases 0.000 claims description 7
- 230000036506 anxiety Effects 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 201000006549 dyspepsia Diseases 0.000 claims description 7
- 230000004761 fibrosis Effects 0.000 claims description 7
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 7
- 206010027599 migraine Diseases 0.000 claims description 7
- 208000004296 neuralgia Diseases 0.000 claims description 7
- 230000000414 obstructive effect Effects 0.000 claims description 7
- 208000019906 panic disease Diseases 0.000 claims description 7
- 201000011264 priapism Diseases 0.000 claims description 7
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 7
- 238000007634 remodeling Methods 0.000 claims description 7
- 208000023504 respiratory system disease Diseases 0.000 claims description 7
- 208000019116 sleep disease Diseases 0.000 claims description 7
- 208000020685 sleep-wake disease Diseases 0.000 claims description 7
- 230000036263 tachygastria Effects 0.000 claims description 7
- 208000005171 Dysmenorrhea Diseases 0.000 claims description 6
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 6
- 206010036600 Premature labour Diseases 0.000 claims description 6
- 208000016599 Uterine disease Diseases 0.000 claims description 6
- 230000030135 gastric motility Effects 0.000 claims description 6
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims description 5
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims description 5
- 208000026440 premature labor Diseases 0.000 claims description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 230000003042 antagnostic effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 230000008485 antagonism Effects 0.000 claims description 2
- 238000011285 therapeutic regimen Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 116
- 239000000203 mixture Substances 0.000 description 104
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 94
- 238000005481 NMR spectroscopy Methods 0.000 description 65
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- 239000007787 solid Substances 0.000 description 59
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- 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 50
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 38
- 239000000243 solution Substances 0.000 description 38
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 36
- 125000000623 heterocyclic group Chemical group 0.000 description 36
- 238000001819 mass spectrum Methods 0.000 description 36
- 239000012267 brine Substances 0.000 description 32
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 25
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 20
- 239000003208 petroleum Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 125000006413 ring segment Chemical group 0.000 description 18
- 238000010898 silica gel chromatography Methods 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 125000003277 amino group Chemical group 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 125000000753 cycloalkyl group Chemical group 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 125000000524 functional group Chemical group 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 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
- 230000027455 binding Effects 0.000 description 12
- 238000001816 cooling Methods 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
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 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 9
- RTKUGSSNEWHBGJ-UHFFFAOYSA-N 5-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound O1C(N)=NC=C1C1=CC=CC2=CC=CC=C12 RTKUGSSNEWHBGJ-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 101150041968 CDC13 gene Proteins 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000004452 microanalysis Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 239000012131 assay buffer Substances 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 8
- JUWCKQWZKLRALF-UHFFFAOYSA-N 5-(7-bromonaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound O1C(N)=NC=C1C1=CC=CC2=CC=C(Br)C=C12 JUWCKQWZKLRALF-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 235000019502 Orange oil Nutrition 0.000 description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 7
- 239000000872 buffer Substances 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 125000000468 ketone group Chemical group 0.000 description 7
- 239000010502 orange oil Substances 0.000 description 7
- QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- FGZJTYQVOKKPSJ-UHFFFAOYSA-N 2-bromo-1-naphthalen-1-ylpropan-1-one Chemical compound C1=CC=C2C(C(=O)C(Br)C)=CC=CC2=C1 FGZJTYQVOKKPSJ-UHFFFAOYSA-N 0.000 description 6
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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- 238000003556 assay Methods 0.000 description 6
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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- 230000008018 melting Effects 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 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 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
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- 229920006395 saturated elastomer Polymers 0.000 description 6
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- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
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- QQGFVHLDJIRGAD-UHFFFAOYSA-N 5-(4-fluoronaphthalen-1-yl)-4-propan-2-yl-1,3-oxazol-2-amine Chemical compound N1=C(N)OC(C=2C3=CC=CC=C3C(F)=CC=2)=C1C(C)C QQGFVHLDJIRGAD-UHFFFAOYSA-N 0.000 description 5
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- 125000005488 carboaryl group Chemical group 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- 125000005842 heteroatom Chemical group 0.000 description 5
- UKEOUNLPPHKRLM-UHFFFAOYSA-N n-(5-naphthalen-1-yl-1,3-oxazol-2-yl)acetamide Chemical compound O1C(NC(=O)C)=NC=C1C1=CC=CC2=CC=CC=C12 UKEOUNLPPHKRLM-UHFFFAOYSA-N 0.000 description 5
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- 231100000252 nontoxic Toxicity 0.000 description 5
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 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
- 229940005605 valeric acid Drugs 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 (2)
| Publication Number | Publication Date |
|---|---|
| NO20043799L NO20043799L (no) | 2004-09-10 |
| NO327465B1 true NO327465B1 (no) | 2009-07-06 |
Family
ID=9930999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20043799A NO327465B1 (no) | 2002-02-13 | 2004-09-10 | 2-oksasolaminer og deres anvendelse samt farmasoytisk sammensetning |
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 |
| MXPA04007738A (es) | 2004-10-15 |
| NZ534539A (en) | 2006-02-24 |
| US7429607B2 (en) | 2008-09-30 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |