NO810548L - Fremgangsmaate ved fremstilling av nye, terapeutisk virksomme piperidinokinazoliner - Google Patents
Fremgangsmaate ved fremstilling av nye, terapeutisk virksomme piperidinokinazolinerInfo
- Publication number
- NO810548L NO810548L NO810548A NO810548A NO810548L NO 810548 L NO810548 L NO 810548L NO 810548 A NO810548 A NO 810548A NO 810548 A NO810548 A NO 810548A NO 810548 L NO810548 L NO 810548L
- Authority
- NO
- Norway
- Prior art keywords
- amino
- formula
- group
- cyano
- dimethoxyquinazoline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 2-substituted 4,5-dimethoxyaniline Chemical class 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- DMCSURRPVDKJIM-UHFFFAOYSA-N 6,7-dimethoxy-2-piperidin-1-ylquinazolin-4-amine Chemical class N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCCCC1 DMCSURRPVDKJIM-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- 239000007858 starting material Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000036772 blood pressure Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- PRLBEZUIQAZHSY-UHFFFAOYSA-N [1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-pyrrolidin-1-ylmethanone;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1C(=O)N1CCCC1 PRLBEZUIQAZHSY-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 6
- 229960001289 prazosin Drugs 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HDRVDMLSGZSRGF-UHFFFAOYSA-N [1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-3-yl]-pyrrolidin-1-ylmethanone;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(C1)CCCC1C(=O)N1CCCC1 HDRVDMLSGZSRGF-UHFFFAOYSA-N 0.000 description 4
- KBGWVPWFNVDPJK-UHFFFAOYSA-N ethyl 1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 KBGWVPWFNVDPJK-UHFFFAOYSA-N 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BJAYMNUBIULRMF-UHFFFAOYSA-N 2-amino-4,5-dimethoxybenzonitrile Chemical compound COC1=CC(N)=C(C#N)C=C1OC BJAYMNUBIULRMF-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- XSZGVLNDRGNJGT-UHFFFAOYSA-N [1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-3-yl]-pyrrolidin-1-ylmethanone Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(C1)CCCC1C(=O)N1CCCC1 XSZGVLNDRGNJGT-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ILRTXPKUUOBHNH-UHFFFAOYSA-N 1-(4-amino-6,7-dimethoxyquinazolin-2-yl)-n-tert-butylpiperidine-4-carboxamide;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCC(C(=O)NC(C)(C)C)CC1 ILRTXPKUUOBHNH-UHFFFAOYSA-N 0.000 description 2
- MYPWLRMBIOBPLJ-UHFFFAOYSA-N 1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidine-4-carboxamide;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCC(C(N)=O)CC1 MYPWLRMBIOBPLJ-UHFFFAOYSA-N 0.000 description 2
- MGHPNHISKDKRJW-UHFFFAOYSA-N 6,7-dimethoxyquinazolin-4-amine Chemical compound C1=NC(N)=C2C=C(OC)C(OC)=CC2=N1 MGHPNHISKDKRJW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- OSVXKXQRXRSBEO-UHFFFAOYSA-N [1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-(2,5-dimethylpyrrolidin-1-yl)methanone;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1C(=O)N1C(C)CCC1C OSVXKXQRXRSBEO-UHFFFAOYSA-N 0.000 description 2
- PJGPWPCICXNSGH-UHFFFAOYSA-N [1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-(2,6-dimethylpiperidin-1-yl)methanone;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1C(=O)N1C(C)CCCC1C PJGPWPCICXNSGH-UHFFFAOYSA-N 0.000 description 2
- WZJVRABYEMQNGO-UHFFFAOYSA-N [1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-(2-methylpiperidin-1-yl)methanone;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1C(=O)N1CCCCC1C WZJVRABYEMQNGO-UHFFFAOYSA-N 0.000 description 2
- IPIOFGYLENXRIB-UHFFFAOYSA-N [1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-(azepan-1-yl)methanone;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1C(=O)N1CCCCCC1 IPIOFGYLENXRIB-UHFFFAOYSA-N 0.000 description 2
- CSYUZZJFUKXXMG-UHFFFAOYSA-N [1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-(azocan-1-yl)methanone;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1C(=O)N1CCCCCCC1 CSYUZZJFUKXXMG-UHFFFAOYSA-N 0.000 description 2
- AVXZPBFXCSERAM-UHFFFAOYSA-N [1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-cyclohexylmethanone;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1C(=O)C1CCCCC1 AVXZPBFXCSERAM-UHFFFAOYSA-N 0.000 description 2
- BOVBYXTWAFNRAV-UHFFFAOYSA-N [1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-piperidin-1-ylmethanone Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1C(=O)N1CCCCC1 BOVBYXTWAFNRAV-UHFFFAOYSA-N 0.000 description 2
- ZVBXQRCYSMONRC-UHFFFAOYSA-N [1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]-pyrrolidin-1-ylmethanone Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1C(=O)N1CCCC1 ZVBXQRCYSMONRC-UHFFFAOYSA-N 0.000 description 2
- VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 2
- 230000004531 blood pressure lowering effect Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- RULTUDDYFVDTKF-UHFFFAOYSA-N ethyl 1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidine-4-carboxylate;hydrochloride Chemical compound Cl.C1CC(C(=O)OCC)CCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 RULTUDDYFVDTKF-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- JQCRUYLUQJNZIC-UHFFFAOYSA-N piperidin-4-yl(pyrrolidin-1-yl)methanone Chemical compound C1CCCN1C(=O)C1CCNCC1 JQCRUYLUQJNZIC-UHFFFAOYSA-N 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- VMKQIIHXIOEFLH-UHFFFAOYSA-N (3,4-dimethoxyphenyl)thiourea Chemical compound COC1=CC=C(NC(N)=S)C=C1OC VMKQIIHXIOEFLH-UHFFFAOYSA-N 0.000 description 1
- BZVLFFLBEOOKLA-UHFFFAOYSA-N 1-(4-amino-6,7-dimethoxyquinazolin-2-yl)-n,n-diethylpiperidine-2-carboxamide Chemical compound CCN(CC)C(=O)C1CCCCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 BZVLFFLBEOOKLA-UHFFFAOYSA-N 0.000 description 1
- MNNCQPMAZRRFNS-UHFFFAOYSA-N 1-(4-amino-6,7-dimethoxyquinazolin-2-yl)-n,n-diethylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(CC)CC)CCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 MNNCQPMAZRRFNS-UHFFFAOYSA-N 0.000 description 1
- LEPYKPPBAQMWDW-UHFFFAOYSA-N 1-(4-amino-6,7-dimethoxyquinazolin-2-yl)-n-butylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NCCCC)CCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 LEPYKPPBAQMWDW-UHFFFAOYSA-N 0.000 description 1
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- GUNIFUVPXYLHNG-UHFFFAOYSA-N 1-[1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]ethanone;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCC(C(C)=O)CC1 GUNIFUVPXYLHNG-UHFFFAOYSA-N 0.000 description 1
- BHFFTAOFOBYFPX-UHFFFAOYSA-N 1-[1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]pentan-1-one;hydrochloride Chemical compound Cl.C1CC(C(=O)CCCC)CCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 BHFFTAOFOBYFPX-UHFFFAOYSA-N 0.000 description 1
- MJUZBRXMCUISCA-UHFFFAOYSA-N 1-[1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]propan-1-one;hydrochloride Chemical compound Cl.C1CC(C(=O)CC)CCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 MJUZBRXMCUISCA-UHFFFAOYSA-N 0.000 description 1
- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical compound C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 description 1
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- JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
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- FYMQPWWNOCENRN-UHFFFAOYSA-N 6,7-dimethoxyquinazoline Chemical compound N1=CN=C2C=C(OC)C(OC)=CC2=C1 FYMQPWWNOCENRN-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
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- 239000012535 impurity Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- YNXURHRFIMQACJ-UHFFFAOYSA-N lithium;methanidylbenzene Chemical compound [Li+].[CH2-]C1=CC=CC=C1 YNXURHRFIMQACJ-UHFFFAOYSA-N 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- VBUBADWLHFZFDK-UHFFFAOYSA-N quinazoline;hydrochloride Chemical compound Cl.N1=CN=CC2=CC=CC=C21 VBUBADWLHFZFDK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000004873 systolic arterial blood pressure Effects 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI800481A FI800481A (fi) | 1980-02-19 | 1980-02-19 | Foerfarande foer framstaellning av substituerade acylpiperidiner |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO810548L true NO810548L (no) | 1981-08-20 |
Family
ID=8513260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO810548A NO810548L (no) | 1980-02-19 | 1981-02-18 | Fremgangsmaate ved fremstilling av nye, terapeutisk virksomme piperidinokinazoliner |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0034471A1 (es) |
| JP (1) | JPS56131578A (es) |
| AR (1) | AR228051A1 (es) |
| AU (1) | AU6739681A (es) |
| BG (1) | BG35041A3 (es) |
| DD (1) | DD158775A5 (es) |
| DK (1) | DK71681A (es) |
| ES (1) | ES499558A0 (es) |
| FI (1) | FI800481A (es) |
| GR (1) | GR66282B (es) |
| IL (1) | IL62113A0 (es) |
| IN (1) | IN152325B (es) |
| NO (1) | NO810548L (es) |
| NZ (1) | NZ196229A (es) |
| PL (1) | PL229760A1 (es) |
| PT (1) | PT72510B (es) |
| SU (1) | SU1042616A3 (es) |
| YU (1) | YU34181A (es) |
| ZA (1) | ZA81902B (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES515338A0 (es) * | 1981-09-09 | 1983-11-01 | Orion Yhtymae Oy | "metodo para la preparacion de piperidinilquinazolidinas substituidas". |
| CA2077252C (en) * | 1992-08-31 | 2001-04-10 | Khashayar Karimian | Methods of making ureas and guanidines, and intermediates therefor |
| AU2009315761A1 (en) | 2008-11-14 | 2010-05-20 | F. Hoffmann-La Roche Ag | Quinazoline derivatives as NK3 receptor antagonists |
| TWI771327B (zh) * | 2016-10-05 | 2022-07-21 | 英商使命醫療公司 | 新穎化合物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2321890A1 (fr) * | 1975-08-26 | 1977-03-25 | Synthelabo | Nouveaux derives de la quinazoline, leurs sels, leur preparation et les medicaments qui en renferment |
-
1980
- 1980-02-19 FI FI800481A patent/FI800481A/fi not_active Application Discontinuation
-
1981
- 1981-02-10 NZ NZ196229A patent/NZ196229A/xx unknown
- 1981-02-10 YU YU00341/81A patent/YU34181A/xx unknown
- 1981-02-11 IL IL62113A patent/IL62113A0/xx unknown
- 1981-02-11 ZA ZA00810902A patent/ZA81902B/xx unknown
- 1981-02-12 EP EP81300579A patent/EP0034471A1/en not_active Withdrawn
- 1981-02-16 PT PT72510A patent/PT72510B/pt unknown
- 1981-02-18 AU AU67396/81A patent/AU6739681A/en not_active Abandoned
- 1981-02-18 SU SU813250801A patent/SU1042616A3/ru active
- 1981-02-18 DK DK71681A patent/DK71681A/da not_active Application Discontinuation
- 1981-02-18 NO NO810548A patent/NO810548L/no unknown
- 1981-02-18 GR GR64174A patent/GR66282B/el unknown
- 1981-02-18 BG BG050877A patent/BG35041A3/xx unknown
- 1981-02-18 ES ES499558A patent/ES499558A0/es active Granted
- 1981-02-19 PL PL22976081A patent/PL229760A1/xx unknown
- 1981-02-19 JP JP2231581A patent/JPS56131578A/ja active Pending
- 1981-02-19 DD DD81227758A patent/DD158775A5/de unknown
- 1981-02-19 AR AR284351A patent/AR228051A1/es active
- 1981-02-20 IN IN198/CAL/81A patent/IN152325B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DD158775A5 (de) | 1983-02-02 |
| IN152325B (es) | 1983-12-17 |
| BG35041A3 (en) | 1984-01-16 |
| AU6739681A (en) | 1981-08-27 |
| ES8301963A1 (es) | 1982-12-16 |
| DK71681A (da) | 1981-08-20 |
| YU34181A (en) | 1983-10-31 |
| JPS56131578A (en) | 1981-10-15 |
| EP0034471A1 (en) | 1981-08-26 |
| PT72510A (en) | 1981-03-01 |
| FI800481A (fi) | 1981-08-20 |
| AR228051A1 (es) | 1983-01-14 |
| ES499558A0 (es) | 1982-12-16 |
| ZA81902B (en) | 1982-02-24 |
| SU1042616A3 (ru) | 1983-09-15 |
| GR66282B (es) | 1981-02-20 |
| PT72510B (en) | 1983-02-01 |
| PL229760A1 (es) | 1982-04-13 |
| IL62113A0 (en) | 1981-03-31 |
| NZ196229A (en) | 1983-02-15 |
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