NO331845B1 - Nye forbindelser, anvendelse derav for a forebygge eller behandle bentilstander, og farmasoytiske sammensetninger med slike forbindelser - Google Patents
Nye forbindelser, anvendelse derav for a forebygge eller behandle bentilstander, og farmasoytiske sammensetninger med slike forbindelser Download PDFInfo
- Publication number
- NO331845B1 NO331845B1 NO20053498A NO20053498A NO331845B1 NO 331845 B1 NO331845 B1 NO 331845B1 NO 20053498 A NO20053498 A NO 20053498A NO 20053498 A NO20053498 A NO 20053498A NO 331845 B1 NO331845 B1 NO 331845B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- isopropyl
- quinazolin
- prop
- ynyloxy
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 74
- 210000000988 bone and bone Anatomy 0.000 title claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000011575 calcium Substances 0.000 claims abstract description 16
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 16
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 14
- 230000011164 ossification Effects 0.000 claims abstract description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 208000001132 Osteoporosis Diseases 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000000638 stimulation Effects 0.000 claims description 7
- 206010006956 Calcium deficiency Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- WNUBXSUKNMGDHX-UHFFFAOYSA-N 1-[[3-(2-hydroxyethoxy)phenyl]methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazoline-2-thione Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=S)N1CC1=CC=CC(OCCO)=C1 WNUBXSUKNMGDHX-UHFFFAOYSA-N 0.000 claims description 4
- FZHRWFGQFICKQC-UHFFFAOYSA-N 1-benzyl-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazoline-2-thione Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=S)N1CC1=CC=CC=C1 FZHRWFGQFICKQC-UHFFFAOYSA-N 0.000 claims description 4
- MOQMUMSCPKLYMB-UHFFFAOYSA-N 1-benzyl-6-hydroxy-4-(4-propan-2-ylphenyl)-5-prop-2-enylquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=C(CC=C)C(O)=CC=C11)=NC(=O)N1CC1=CC=CC=C1 MOQMUMSCPKLYMB-UHFFFAOYSA-N 0.000 claims description 4
- JTOWEUHRLCFSGP-UHFFFAOYSA-N 1-[(2,3-dimethoxyquinoxalin-6-yl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=C2N=C(OC)C(OC)=NC2=CC=C1CN(C(N=1)=O)C2=CC=C(OCC#C)C=C2C=1C1=CC=C(C(C)C)C=C1 JTOWEUHRLCFSGP-UHFFFAOYSA-N 0.000 claims description 3
- ONIZJZIJALTHQW-UHFFFAOYSA-N 1-[[2-(2-hydroxyethoxy)phenyl]methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=CC=C1OCCO ONIZJZIJALTHQW-UHFFFAOYSA-N 0.000 claims description 3
- KRADDNXZWVNICM-UHFFFAOYSA-N 1-[[2-(2-methoxyethoxy)pyridin-3-yl]methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound COCCOC1=NC=CC=C1CN1C(=O)N=C(C=2C=CC(=CC=2)C(C)C)C2=CC(OCC#C)=CC=C21 KRADDNXZWVNICM-UHFFFAOYSA-N 0.000 claims description 3
- QUYLWAARGNSPMB-UHFFFAOYSA-N 1-[[6-(2-hydroxyethoxy)pyridin-2-yl]methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=CC(OCCO)=N1 QUYLWAARGNSPMB-UHFFFAOYSA-N 0.000 claims description 3
- 208000002679 Alveolar Bone Loss Diseases 0.000 claims description 3
- 208000020084 Bone disease Diseases 0.000 claims description 3
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- 206010003246 arthritis Diseases 0.000 claims description 3
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- 230000002265 prevention Effects 0.000 claims description 3
- WAWKIXZOXFBJLY-UHFFFAOYSA-N 1-(2,2-dimethylpent-4-enyl)-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C1=NC(=O)N(CC(C)(C)CC=C)C2=CC=C(OCC#C)C=C12 WAWKIXZOXFBJLY-UHFFFAOYSA-N 0.000 claims description 2
- AZFLTODXSFWGBV-UHFFFAOYSA-N 1-(2-methylhex-4-enyl)-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound N=1C(=O)N(CC(C)CC=CC)C2=CC=C(OCC#C)C=C2C=1C1=CC=C(C(C)C)C=C1 AZFLTODXSFWGBV-UHFFFAOYSA-N 0.000 claims description 2
- QSTFOTXJPGATJP-UHFFFAOYSA-N 1-(3,3-dimethylbutyl)-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C1=NC(=O)N(CCC(C)(C)C)C2=CC=C(OCC#C)C=C12 QSTFOTXJPGATJP-UHFFFAOYSA-N 0.000 claims description 2
- ITOJTHZRQMLCBG-UHFFFAOYSA-N 1-(3-bromopropyl)-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C1=NC(=O)N(CCCBr)C2=CC=C(OCC#C)C=C12 ITOJTHZRQMLCBG-UHFFFAOYSA-N 0.000 claims description 2
- DSGLFEFJDLRIIM-UHFFFAOYSA-N 1-(3-methylsulfanylpropyl)-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound N=1C(=O)N(CCCSC)C2=CC=C(OCC#C)C=C2C=1C1=CC=C(C(C)C)C=C1 DSGLFEFJDLRIIM-UHFFFAOYSA-N 0.000 claims description 2
- SOHDUTJWMFWXLW-UHFFFAOYSA-N 1-[(2,4-diaminopyrimidin-5-yl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CN=C(N)N=C1N SOHDUTJWMFWXLW-UHFFFAOYSA-N 0.000 claims description 2
- LZZQFBXWXULZEL-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=C(Cl)C=CC=C1Cl LZZQFBXWXULZEL-UHFFFAOYSA-N 0.000 claims description 2
- OFHYTVMRWWJJCL-UHFFFAOYSA-N 1-[(2-butyl-4-chloro-1h-imidazol-5-yl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound N1C(CCCC)=NC(CN2C(N=C(C3=CC(OCC#C)=CC=C32)C=2C=CC(=CC=2)C(C)C)=O)=C1Cl OFHYTVMRWWJJCL-UHFFFAOYSA-N 0.000 claims description 2
- CCTYICLJLGAWFF-UHFFFAOYSA-N 1-[(2-chloropyridin-3-yl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=CN=C1Cl CCTYICLJLGAWFF-UHFFFAOYSA-N 0.000 claims description 2
- PPAVKZLVZLYFGX-UHFFFAOYSA-N 1-[(2-chloropyridin-4-yl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=NC(Cl)=C1 PPAVKZLVZLYFGX-UHFFFAOYSA-N 0.000 claims description 2
- CIZOLISLHNIUSW-UHFFFAOYSA-N 1-[(2-methoxyphenyl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound COC1=CC=CC=C1CN1C(=O)N=C(C=2C=CC(=CC=2)C(C)C)C2=CC(OCC#C)=CC=C21 CIZOLISLHNIUSW-UHFFFAOYSA-N 0.000 claims description 2
- DATYCBHDXBVGCV-UHFFFAOYSA-N 1-[(2-oxo-1h-pyridin-3-yl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=CN=C1O DATYCBHDXBVGCV-UHFFFAOYSA-N 0.000 claims description 2
- IGAUNRUWFHIZSB-UHFFFAOYSA-N 1-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 IGAUNRUWFHIZSB-UHFFFAOYSA-N 0.000 claims description 2
- IIBRYYCFSIBSFT-UHFFFAOYSA-N 1-[(3-ethoxy-4-methoxyphenyl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=C(OC)C(OCC)=CC(CN2C(N=C(C3=CC(OCC#C)=CC=C32)C=2C=CC(=CC=2)C(C)C)=O)=C1 IIBRYYCFSIBSFT-UHFFFAOYSA-N 0.000 claims description 2
- CXXFLOXCTONKPM-UHFFFAOYSA-N 1-[(3-methylsulfinylphenyl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=CC(S(C)=O)=C1 CXXFLOXCTONKPM-UHFFFAOYSA-N 0.000 claims description 2
- QDRDRRIVPQODOZ-UHFFFAOYSA-N 1-[(3-methylsulfonylphenyl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=CC(S(C)(=O)=O)=C1 QDRDRRIVPQODOZ-UHFFFAOYSA-N 0.000 claims description 2
- KIZITKARUSPCHY-UHFFFAOYSA-N 1-[(4-bromophenyl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=C(Br)C=C1 KIZITKARUSPCHY-UHFFFAOYSA-N 0.000 claims description 2
- WZPYWVQODKUCET-UHFFFAOYSA-N 1-[(5-bromothiophen-2-yl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=C(Br)S1 WZPYWVQODKUCET-UHFFFAOYSA-N 0.000 claims description 2
- QCLQPFPFVBOVJY-UHFFFAOYSA-N 1-[(6-methoxypyridin-3-yl)methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=NC(OC)=CC=C1CN1C(=O)N=C(C=2C=CC(=CC=2)C(C)C)C2=CC(OCC#C)=CC=C21 QCLQPFPFVBOVJY-UHFFFAOYSA-N 0.000 claims description 2
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- SPCKNUOUUWVWLY-UHFFFAOYSA-N 1-[2-(3,5-difluorophenyl)-2-hydroxyethyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC(O)C1=CC(F)=CC(F)=C1 SPCKNUOUUWVWLY-UHFFFAOYSA-N 0.000 claims description 2
- JGWYBODYOPDXRT-UHFFFAOYSA-N 1-[2-(3,5-dimethoxyphenyl)ethyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound COC1=CC(OC)=CC(CCN2C(N=C(C3=CC(OCC#C)=CC=C32)C=2C=CC(=CC=2)C(C)C)=O)=C1 JGWYBODYOPDXRT-UHFFFAOYSA-N 0.000 claims description 2
- LMMPWVOPAUIKGL-UHFFFAOYSA-N 1-[2-hydroxy-2-(2,4,6-trimethylphenyl)ethyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC(O)C1=C(C)C=C(C)C=C1C LMMPWVOPAUIKGL-UHFFFAOYSA-N 0.000 claims description 2
- WAJNWFGEVCJWCF-UHFFFAOYSA-N 1-[[4-[2-[methyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC(C=C1)=CC=C1OCCN(C)C1=CC=CC=N1 WAJNWFGEVCJWCF-UHFFFAOYSA-N 0.000 claims description 2
- WQMPJQSEVCPQJU-UHFFFAOYSA-N 1-[[6-(hydroxymethyl)pyridin-2-yl]methyl]-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=CC(CO)=N1 WQMPJQSEVCPQJU-UHFFFAOYSA-N 0.000 claims description 2
- HOTAYWVTZKVGLN-UHFFFAOYSA-N 4-(4-propan-2-ylphenyl)-6-prop-2-ynoxy-1-(3,3,3-trifluoropropyl)quinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C1=NC(=O)N(CCC(F)(F)F)C2=CC=C(OCC#C)C=C12 HOTAYWVTZKVGLN-UHFFFAOYSA-N 0.000 claims description 2
- JVQRYSPDSHAIMN-UHFFFAOYSA-N 4-(4-propan-2-ylphenyl)-6-prop-2-ynoxy-1-(pyridin-2-ylmethyl)quinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=CC=N1 JVQRYSPDSHAIMN-UHFFFAOYSA-N 0.000 claims description 2
- BDECDLHANFXDJY-UHFFFAOYSA-N 4-(4-propan-2-ylphenyl)-6-prop-2-ynoxy-1-(pyridin-3-ylmethyl)quinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=CN=C1 BDECDLHANFXDJY-UHFFFAOYSA-N 0.000 claims description 2
- JVIQESIAMKQPQU-UHFFFAOYSA-N 4-(4-propan-2-ylphenyl)-6-prop-2-ynoxy-1-(thiophen-2-ylmethyl)quinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=CS1 JVIQESIAMKQPQU-UHFFFAOYSA-N 0.000 claims description 2
- ZJEMENKDYCZBFW-UHFFFAOYSA-N 4-(4-propan-2-ylphenyl)-6-prop-2-ynoxy-1-(thiophen-2-ylmethyl)quinazoline-2-thione Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=S)N1CC1=CC=CS1 ZJEMENKDYCZBFW-UHFFFAOYSA-N 0.000 claims description 2
- QFHVFMRKECVFSV-UHFFFAOYSA-N 4-(4-propan-2-ylphenyl)-6-prop-2-ynoxy-1-[(4-pyrazin-2-ylphenyl)methyl]quinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=C(C=2N=CC=NC=2)C=C1 QFHVFMRKECVFSV-UHFFFAOYSA-N 0.000 claims description 2
- DQRPCOXQVRAJSZ-CCEZHUSRSA-N 4-(4-propan-2-ylphenyl)-6-prop-2-ynoxy-1-[(e)-2-(2,4,6-trimethylphenyl)ethenyl]quinazolin-2-one Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1\C=C\C1=C(C)C=C(C)C=C1C DQRPCOXQVRAJSZ-CCEZHUSRSA-N 0.000 claims description 2
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- POEBCARWIIPIMG-UHFFFAOYSA-N 7-[[2-oxo-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-1-yl]methyl]-1h-indole-2-carbonitrile Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1=CC=CC2=C1NC(C#N)=C2 POEBCARWIIPIMG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- UBQAUQQIYRRCOB-UHFFFAOYSA-N tert-butyl 2,2-dimethyl-4-[[2-oxo-4-(4-propan-2-ylphenyl)-6-prop-2-ynoxyquinazolin-1-yl]methyl]-1,3-oxazolidine-3-carboxylate Chemical compound C1=CC(C(C)C)=CC=C1C(C1=CC(OCC#C)=CC=C11)=NC(=O)N1CC1N(C(=O)OC(C)(C)C)C(C)(C)OC1 UBQAUQQIYRRCOB-UHFFFAOYSA-N 0.000 claims description 2
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- OGBMKVWORPGQRR-UMXFMPSGSA-N teriparatide Chemical compound C([C@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H](N)CO)C(C)C)[C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CNC=N1 OGBMKVWORPGQRR-UMXFMPSGSA-N 0.000 description 1
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Classifications
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- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
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- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
- C07D413/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
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PCT/EP2003/014741 WO2004056365A2 (fr) | 2002-12-23 | 2003-12-22 | Derives d'aryl-quinazoline/aryl-2amino-phenyl methanone |
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EP (2) | EP1844780A3 (fr) |
JP (2) | JP4485956B2 (fr) |
KR (2) | KR20070097136A (fr) |
CN (2) | CN1732002A (fr) |
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AT (1) | ATE398450T1 (fr) |
AU (1) | AU2003296710B2 (fr) |
BR (1) | BR0316877A (fr) |
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DE (1) | DE60321722D1 (fr) |
EC (1) | ECSP055888A (fr) |
ES (1) | ES2308041T3 (fr) |
GB (1) | GB0230015D0 (fr) |
HK (1) | HK1084043A1 (fr) |
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MY (1) | MY152921A (fr) |
NO (1) | NO331845B1 (fr) |
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PL (1) | PL378916A1 (fr) |
PT (1) | PT1585521E (fr) |
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TW (1) | TWI333952B (fr) |
WO (1) | WO2004056365A2 (fr) |
ZA (1) | ZA200504386B (fr) |
Families Citing this family (24)
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AR038658A1 (es) | 2001-06-15 | 2005-01-26 | Novartis Ag | Derivados de 4-aril-2(1h) quinazolinona y 4-aril-quinazolina 2-sustituidas, un proceso para su preparacion, composiciones farmaceuticas y el uso de dichos derivados para la preparacion de un medicamento |
GB0230015D0 (en) * | 2002-12-23 | 2003-01-29 | Novartis Ag | Organic compounds |
DK2821067T3 (en) | 2003-09-12 | 2017-12-04 | Amgen Inc | Quick solution formulation of cinacalcet |
EP1671961A4 (fr) * | 2003-09-17 | 2009-04-01 | Sumitomo Chemical Co | Compose cinnamoyle et utilisation associee |
GB0516723D0 (en) * | 2005-08-15 | 2005-09-21 | Novartis Ag | Organic compounds |
CN101547922B (zh) * | 2006-10-04 | 2012-06-20 | 辉瑞产品公司 | 作为钙受体拮抗剂的吡啶并[4,3-d]嘧啶-4(3H)-酮衍生物 |
EP1956019A1 (fr) * | 2007-01-22 | 2008-08-13 | Novartis AG | Dérivés de benzoquinazoline |
US7928111B2 (en) | 2007-06-08 | 2011-04-19 | Senomyx, Inc. | Compounds including substituted thienopyrimidinone derivatives as ligands for modulating chemosensory receptors |
US9603848B2 (en) | 2007-06-08 | 2017-03-28 | Senomyx, Inc. | Modulation of chemosensory receptors and ligands associated therewith |
EP2323997B1 (fr) | 2008-07-31 | 2017-09-06 | Senomyx, Inc. | Procédés et intermédiaires pour la réalisation d`exhausteurs de goût sucré |
WO2010136037A1 (fr) | 2009-05-27 | 2010-12-02 | Leo Pharma A/S | Nouveaux composés modulant le récepteur sensible au calcium, et leur utilisation pharmaceutique |
US8785494B2 (en) | 2009-05-27 | 2014-07-22 | Leo-Pharma A/S | Calcium sensing receptor modulating compounds and pharmaceutical use thereof |
JP2014508103A (ja) | 2010-11-26 | 2014-04-03 | レオ ファーマ アクティーゼルスカブ | カルシウム感知受容体活性化合物 |
CN103391920A (zh) | 2010-11-26 | 2013-11-13 | 利奥制药有限公司 | 钙敏感受体激活化合物 |
WO2012069420A2 (fr) | 2010-11-26 | 2012-05-31 | Leo Pharma A/S | Composés actifs sur le récepteur sensible au calcium |
RU2013128950A (ru) | 2010-11-26 | 2015-01-10 | Лео Фарма А/С | Замещенные циклопентилазины в качестве casr-активных соединений |
KR20150041040A (ko) | 2012-08-06 | 2015-04-15 | 세노믹스, 인코포레이티드 | 단맛 향미 개질제 |
CN103848781B (zh) * | 2012-11-30 | 2017-06-30 | 重庆华邦制药有限公司 | 高选择性氧化二羟甲基吡啶中一个羟甲基的方法 |
JO3155B1 (ar) | 2013-02-19 | 2017-09-20 | Senomyx Inc | معدِّل نكهة حلوة |
CN104387317B (zh) * | 2014-11-27 | 2017-05-10 | 安徽星宇化工有限公司 | 一种6‑氯烟酸的制备方法及分离纯化方法 |
MX2021001193A (es) | 2018-08-07 | 2021-04-28 | Firmenich Incorporated | 2,2-dioxidos de 4-amino-1h-benzo[c][1,2,6]tiadiazina 5-sustituidos y formulaciones y usos de los mismos. |
WO2021029517A1 (fr) * | 2019-08-13 | 2021-02-18 | Dongguk University Industry-Academic Cooperation Foundation | Composition pharmaceutique destinée à améliorer ou traiter l'hypoparathyroïdie post-chirurgicale et méthode de traitement l'utilisant |
CN113967249A (zh) * | 2021-12-10 | 2022-01-25 | 深圳先进技术研究院 | 甲状旁腺激素在制备治疗男性抑郁症的药物或保健品中的应用 |
CN114591188B (zh) * | 2022-04-02 | 2023-06-09 | 南京工业大学 | 一种全生物基芳基二胺扩链剂及其制备方法与应用 |
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BG16442A3 (bg) | 1967-10-30 | 1972-11-20 | Max Denzer | Метод за получаване на нови о-изопропиламинобензофенони |
BG16042A3 (bg) * | 1968-11-12 | 1972-05-20 | Nans Ott | Метод за получаване на нови 2(1н)-хиназолинони |
US3712892A (en) | 1969-08-02 | 1973-01-23 | Sumitomo Chemical Co | Quinazolinone derivatives |
DE2137008A1 (de) * | 1970-10-21 | 1972-04-27 | Zellweger Uster Ag | Verfahren und Vorrichtung zur automatischen Ablesung von Informationsträgern an Gegenständen |
JPS5118423B1 (fr) * | 1970-12-08 | 1976-06-09 | ||
BE790804A (fr) * | 1971-11-18 | 1973-04-30 | Sandoz Sa | Procede de preparation de derives de la quinazoline |
US3812257A (en) * | 1972-04-07 | 1974-05-21 | Sumitomo Chemical Co | Uricosuric agent |
JPS5418269B2 (fr) * | 1972-07-20 | 1979-07-06 | ||
JPS555506B2 (fr) * | 1972-09-07 | 1980-02-07 | ||
US4067868A (en) * | 1973-04-17 | 1978-01-10 | Sumitomo Chemical Company, Limited | Production of quinazolinone compounds |
JPS5046680A (fr) * | 1973-08-20 | 1975-04-25 | ||
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JPS518287A (en) | 1974-07-13 | 1976-01-23 | Sumitomo Chemical Co | Kinazorinonjudotaioyobi sonoenno seizoho |
JPS5251379A (en) * | 1975-10-24 | 1977-04-25 | Sumitomo Chem Co Ltd | Preparation 3,4-dihydro-2(1h)-quinazoline derivates |
JPS5271483A (en) * | 1975-12-11 | 1977-06-14 | Sumitomo Chem Co Ltd | Synthesis of 2(1h)-quinazolinone derivatives |
CH625512A5 (fr) * | 1976-12-13 | 1981-09-30 | Sandoz Ag | |
US4171441A (en) * | 1977-09-06 | 1979-10-16 | Sandoz, Inc. | Preparation of quinazolin-2(1H)-ones |
JPS55143959A (en) * | 1979-04-26 | 1980-11-10 | Shionogi & Co Ltd | 2-acylbenzcyanamide derivative |
JPS5795966A (en) | 1980-12-04 | 1982-06-15 | Sumitomo Chem Co Ltd | Novel 2(1h)-quinazolinone derivative |
JP3142638B2 (ja) * | 1991-06-21 | 2001-03-07 | 三井化学株式会社 | 感熱記録材料およびフェノール化合物 |
ATE188377T1 (de) | 1993-06-29 | 2000-01-15 | Takeda Chemical Industries Ltd | Chinoline oder chinazolin-derivate und deren verwendung zur herstellung eines medikaments für die behandlung von osteoporose |
NZ297157A (en) * | 1994-10-21 | 1999-08-30 | Nps Pharma Inc | Amine derivatives with calcium ion receptor activity; medicaments containing such compounds |
US5773663A (en) * | 1996-05-01 | 1998-06-30 | American Cyanamid Company | Fungicidal methods, compounds and compositions containing benzophenones |
CN1244091C (zh) * | 1995-08-22 | 2006-03-01 | 松下电器产业株式会社 | 光盘记录和/或重放装置及设定记录功率及清除功率的方法 |
WO1997014681A1 (fr) * | 1995-10-16 | 1997-04-24 | Fujisawa Pharmaceutical Co., Ltd. | Composes heterocycliques tels que des h+-atpases |
CA2190708A1 (fr) * | 1995-12-08 | 1997-06-09 | Johannes Aebi | Derives de substitution aminoalkyles de composes benzo-heterocycliques |
JPH11209350A (ja) | 1998-01-26 | 1999-08-03 | Eisai Co Ltd | 含窒素複素環誘導体およびその医薬 |
US6358959B1 (en) | 1999-01-26 | 2002-03-19 | Merck & Co., Inc. | Polyazanaphthalenone derivatives useful as alpha 1a adrenoceptor antagonists |
JP2001302515A (ja) | 2000-04-18 | 2001-10-31 | Sumitomo Pharmaceut Co Ltd | ポリ(adp−リボース)ポリメラーゼ阻害剤 |
US7173040B2 (en) * | 2000-09-25 | 2007-02-06 | Janssen Pharmaceutica N.V. | Farnesyl transferase inhibiting 6-[(substituted phenyl)methyl]-quinoline and quinazoline derinazoline derivatives |
DE10058347A1 (de) | 2000-11-23 | 2002-06-13 | Petra Bauersachs | Konvergenz-Boxen-Set |
AR038658A1 (es) * | 2001-06-15 | 2005-01-26 | Novartis Ag | Derivados de 4-aril-2(1h) quinazolinona y 4-aril-quinazolina 2-sustituidas, un proceso para su preparacion, composiciones farmaceuticas y el uso de dichos derivados para la preparacion de un medicamento |
GB0230015D0 (en) * | 2002-12-23 | 2003-01-29 | Novartis Ag | Organic compounds |
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- 2003-12-22 BR BR0316877-8A patent/BR0316877A/pt active Search and Examination
- 2003-12-22 AT AT03813593T patent/ATE398450T1/de active
- 2003-12-22 KR KR1020057011734A patent/KR100801348B1/ko not_active IP Right Cessation
- 2003-12-22 RU RU2005123329/04A patent/RU2358972C2/ru not_active IP Right Cessation
- 2003-12-22 US US10/540,359 patent/US7696216B2/en not_active Expired - Fee Related
- 2003-12-22 MX MXPA05006866A patent/MXPA05006866A/es active IP Right Grant
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2004
- 2004-01-05 PE PE2004000025A patent/PE20040971A1/es not_active Application Discontinuation
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2005
- 2005-05-30 ZA ZA200504386A patent/ZA200504386B/xx unknown
- 2005-06-15 IL IL169183A patent/IL169183A/en not_active IP Right Cessation
- 2005-06-23 EC EC2005005888A patent/ECSP055888A/es unknown
- 2005-07-18 NO NO20053498A patent/NO331845B1/no not_active IP Right Cessation
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2006
- 2006-04-13 HK HK06104555A patent/HK1084043A1/xx not_active IP Right Cessation
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2009
- 2009-10-15 US US12/579,735 patent/US8569317B2/en not_active Expired - Fee Related
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2010
- 2010-01-22 JP JP2010012104A patent/JP2010159258A/ja active Pending
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