DD143613A5 - Verfahren zur herstellung von 4-amino-2-piperidino-chinazolin-derivaten - Google Patents

Verfahren zur herstellung von 4-amino-2-piperidino-chinazolin-derivaten Download PDF

Info

Publication number: DD143613A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; hydrochloride; preparation; piperidine; amino
Prior art date: 1978-05-18

Application number

DD79213010A

Other languages

German (de)

English (en)

Inventor

Simon F Campbell

John Ch Danilewicz

Colin W Greengrass

Rhona M Plews

Original Assignee

Pfizer

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-05-18

Filing date

1979-05-18

Publication date

1980-09-03

1979-05-18 Application filed by Pfizer filed Critical Pfizer

1980-09-03 Publication of DD143613A5 publication Critical patent/DD143613A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 18
238000002360 preparation method Methods 0.000 claims abstract description 44
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 34
238000000034 method Methods 0.000 claims abstract description 18
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 24
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract description 12
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract description 11
HWIIAAVGRHKSOJ-UHFFFAOYSA-N 2-chloro-6,7-dimethoxyquinazolin-4-amine Chemical compound ClC1=NC(N)=C2C=C(OC)C(OC)=CC2=N1 HWIIAAVGRHKSOJ-UHFFFAOYSA-N 0.000 abstract description 6
206010020772 Hypertension Diseases 0.000 abstract description 6
VBUBADWLHFZFDK-UHFFFAOYSA-N quinazoline;hydrochloride Chemical compound Cl.N1=CN=CC2=CC=CC=C21 VBUBADWLHFZFDK-UHFFFAOYSA-N 0.000 abstract description 5
MDGLKMXWHKGENE-UHFFFAOYSA-N 2-piperidin-1-ylquinazolin-4-amine Chemical class N=1C2=CC=CC=C2C(N)=NC=1N1CCCCC1 MDGLKMXWHKGENE-UHFFFAOYSA-N 0.000 abstract description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 82
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 74
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
238000004458 analytical method Methods 0.000 description 41
239000000243 solution Substances 0.000 description 41
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 37
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
239000007787 solid Substances 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
-1 1,2,3,4-tetrahydroisoquinolyl group Chemical group 0.000 description 17
239000000706 filtrate Substances 0.000 description 17
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
229910000041 hydrogen chloride Inorganic materials 0.000 description 15
239000000203 mixture Substances 0.000 description 15
239000003054 catalyst Substances 0.000 description 12
238000010992 reflux Methods 0.000 description 11
150000003839 salts Chemical class 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
239000011734 sodium Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000002026 chloroform extract Substances 0.000 description 6
239000012043 crude product Substances 0.000 description 6
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 6
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000003814 drug Substances 0.000 description 5
239000012458 free base Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000002808 molecular sieve Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
OVMWUKRHJWOARR-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-yl)oxyacetic acid Chemical compound C1CC(OCC(=O)O)CCN1CC1=CC=CC=C1 OVMWUKRHJWOARR-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
KUBUQFFBRSHOMJ-UHFFFAOYSA-N benzyl 4-carbonochloridoylpiperidine-1-carboxylate Chemical compound C1CC(C(=O)Cl)CCN1C(=O)OCC1=CC=CC=C1 KUBUQFFBRSHOMJ-UHFFFAOYSA-N 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 3
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
150000003053 piperidines Chemical class 0.000 description 3
125000003386 piperidinyl group Chemical group 0.000 description 3
229910003446 platinum oxide Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
KTWOATDVMCBOKL-UHFFFAOYSA-N 2-(2-piperidin-4-yloxyphenyl)acetic acid;hydrochloride Chemical compound Cl.OC(=O)CC1=CC=CC=C1OC1CCNCC1 KTWOATDVMCBOKL-UHFFFAOYSA-N 0.000 description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
101100450563 Mus musculus Serpind1 gene Proteins 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000003276 anti-hypertensive effect Effects 0.000 description 2
239000012223 aqueous fraction Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000012024 dehydrating agents‎ Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
230000036571 hydration Effects 0.000 description 2
238000006703 hydration reaction Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
AKQIYQXGTBXWND-UHFFFAOYSA-N n-phenylpiperidine-4-carboxamide Chemical compound C1CNCCC1C(=O)NC1=CC=CC=C1 AKQIYQXGTBXWND-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
SJUKJZSTBBSGHF-UHFFFAOYSA-N (2,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1Cl SJUKJZSTBBSGHF-UHFFFAOYSA-N 0.000 description 1
QOWBXWFYRXSBAS-UHFFFAOYSA-N (2,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C(OC)=C1 QOWBXWFYRXSBAS-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
LFRHMTZYADABJZ-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)butan-2-amine;hydron;chloride Chemical compound Cl.CCC(N)CC1=CC=C2OCOC2=C1 LFRHMTZYADABJZ-UHFFFAOYSA-N 0.000 description 1
VKAOJUHYNXZMSM-UHFFFAOYSA-N 1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidine-4-carboxylic acid Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCC(C(O)=O)CC1 VKAOJUHYNXZMSM-UHFFFAOYSA-N 0.000 description 1
KZPIFQYDCVCSDS-UHFFFAOYSA-N 1-(4-hydroxypiperidin-1-yl)ethanone Chemical compound CC(=O)N1CCC(O)CC1 KZPIFQYDCVCSDS-UHFFFAOYSA-N 0.000 description 1
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
LQKRZFVMHBKKNN-UHFFFAOYSA-N 2,4-dimethoxyquinazoline;hydrochloride Chemical compound Cl.C1=CC=CC2=NC(OC)=NC(OC)=C21 LQKRZFVMHBKKNN-UHFFFAOYSA-N 0.000 description 1
DWXSYDKEWORWBT-UHFFFAOYSA-N 2-(2-bromophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1Br DWXSYDKEWORWBT-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
RWLHOWNQSKSYQE-UHFFFAOYSA-N 2-[1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]acetic acid Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCC(CC(O)=O)CC1 RWLHOWNQSKSYQE-UHFFFAOYSA-N 0.000 description 1
LSUKBNPACYNGME-UHFFFAOYSA-N 2-[1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]acetic acid;hydrochloride Chemical compound Cl.N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCC(CC(O)=O)CC1 LSUKBNPACYNGME-UHFFFAOYSA-N 0.000 description 1
SVNDNEPMEDTITL-UHFFFAOYSA-N 2-[1-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperidin-4-yl]oxy-2-phenylacetic acid Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCC1OC(C(O)=O)C1=CC=CC=C1 SVNDNEPMEDTITL-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
IYDUFJOXYMLYNM-UHFFFAOYSA-N 2-piperidin-1-ium-4-ylacetic acid;chloride Chemical compound [Cl-].OC(=O)CC1CC[NH2+]CC1 IYDUFJOXYMLYNM-UHFFFAOYSA-N 0.000 description 1
GYMTUXHRQWJXMW-UHFFFAOYSA-N 2-piperidin-1-ylquinazoline Chemical compound C1CCCCN1C1=NC=C(C=CC=C2)C2=N1 GYMTUXHRQWJXMW-UHFFFAOYSA-N 0.000 description 1
XJKGRWLZAWTSOY-UHFFFAOYSA-N 3-piperidin-4-ylpropanoic acid;hydrochloride Chemical compound Cl.OC(=O)CCC1CCNCC1 XJKGRWLZAWTSOY-UHFFFAOYSA-N 0.000 description 1
HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
NVFWFWSKGPTJAR-UHFFFAOYSA-N C(C)(=O)O.NC1=NC(=NC2=CC(=C(C=C12)OC)OC)N1CCC(CC1)OC(C1=CC=CC=C1)C(=O)O Chemical compound C(C)(=O)O.NC1=NC(=NC2=CC(=C(C=C12)OC)OC)N1CCC(CC1)OC(C1=CC=CC=C1)C(=O)O NVFWFWSKGPTJAR-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
VUYCBBHNGBWOJM-UHFFFAOYSA-N NCOCl Chemical compound NCOCl VUYCBBHNGBWOJM-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
WTWYSVJWFSZYQG-UHFFFAOYSA-N benzyl 4-(1-phenylethylcarbamoyl)piperidine-1-carboxylate Chemical compound C=1C=CC=CC=1C(C)NC(=O)C(CC1)CCN1C(=O)OCC1=CC=CC=C1 WTWYSVJWFSZYQG-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Chemical group 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
238000007385 chemical modification Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
229940001468 citrate Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
229940050411 fumarate Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229960002003 hydrochlorothiazide Drugs 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940001447 lactate Drugs 0.000 description 1
239000008101 lactose Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
HOGDNTQCSIKEEV-UHFFFAOYSA-N n'-hydroxybutanediamide Chemical compound NC(=O)CCC(=O)NO HOGDNTQCSIKEEV-UHFFFAOYSA-N 0.000 description 1
PJQBQLWAAJNUTO-UHFFFAOYSA-N n-(1-phenylethyl)piperidine-4-carboxamide Chemical compound C=1C=CC=CC=1C(C)NC(=O)C1CCNCC1 PJQBQLWAAJNUTO-UHFFFAOYSA-N 0.000 description 1
GCDZDXVTDCMNMN-UHFFFAOYSA-N n-(2-aminoethyl)methanesulfonamide Chemical compound CS(=O)(=O)NCCN GCDZDXVTDCMNMN-UHFFFAOYSA-N 0.000 description 1
YESJKZGCXPCJMF-UHFFFAOYSA-N n-(2-aminoethyl)methanesulfonamide;hydrochloride Chemical compound Cl.CS(=O)(=O)NCCN YESJKZGCXPCJMF-UHFFFAOYSA-N 0.000 description 1
CCPJDOCBIGOOSL-UHFFFAOYSA-N n-[(2,4-dimethoxyphenyl)methyl]piperidine-4-carboxamide Chemical compound COC1=CC(OC)=CC=C1CNC(=O)C1CCNCC1 CCPJDOCBIGOOSL-UHFFFAOYSA-N 0.000 description 1
WCKJFDAIYVYUPO-UHFFFAOYSA-N n-[(2-methoxyphenyl)methyl]piperidine-4-carboxamide Chemical compound COC1=CC=CC=C1CNC(=O)C1CCNCC1 WCKJFDAIYVYUPO-UHFFFAOYSA-N 0.000 description 1
KCGJGWKYMLRMOM-UHFFFAOYSA-N n-benzyl-n-methylpiperidine-4-carboxamide Chemical compound C1CNCCC1C(=O)N(C)CC1=CC=CC=C1 KCGJGWKYMLRMOM-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960003966 nicotinamide Drugs 0.000 description 1
235000005152 nicotinamide Nutrition 0.000 description 1
239000011570 nicotinamide Substances 0.000 description 1
DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
ZDYUUBIMAGBMPY-UHFFFAOYSA-N oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O ZDYUUBIMAGBMPY-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
238000000053 physical method Methods 0.000 description 1
ROFVJSWBDQUQGW-UHFFFAOYSA-N piperidin-1-ium;bromide Chemical compound Br.C1CCNCC1 ROFVJSWBDQUQGW-UHFFFAOYSA-N 0.000 description 1
JIYLLYLKTJCEEL-UHFFFAOYSA-N piperidin-4-yl n-ethylcarbamate Chemical compound CCNC(=O)OC1CCNCC1 JIYLLYLKTJCEEL-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
ADYNJDNYIVZXNK-UHFFFAOYSA-N quinazoline;dihydrochloride Chemical compound Cl.Cl.N1=CN=CC2=CC=CC=C21 ADYNJDNYIVZXNK-UHFFFAOYSA-N 0.000 description 1
ZIDNDHOWBISBIO-UHFFFAOYSA-N quinazoline;hydrate;hydrochloride Chemical compound O.Cl.N1=CN=CC2=CC=CC=C21 ZIDNDHOWBISBIO-UHFFFAOYSA-N 0.000 description 1
150000003246 quinazolines Chemical class 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000011699 spontaneously hypertensive rat Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
DBODNPMIIRVQGW-UHFFFAOYSA-N trihydrate;dihydrochloride Chemical compound O.O.O.Cl.Cl DBODNPMIIRVQGW-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- 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
- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyridine Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

DD79213010A 1978-05-18 1979-05-18 Verfahren zur herstellung von 4-amino-2-piperidino-chinazolin-derivaten DD143613A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2035178		1978-05-18

Publications (1)

Publication Number	Publication Date
DD143613A5 true DD143613A5 (de)	1980-09-03

Family

ID=10144517

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79213010A DD143613A5 (de)	1978-05-18	1979-05-18	Verfahren zur herstellung von 4-amino-2-piperidino-chinazolin-derivaten

Country Status (30)

Country	Link
US (1)	US4243666A (fr)
JP (1)	JPS554370A (fr)
AR (2)	AR223487A1 (fr)
AT (1)	ATA363379A (fr)
AU (1)	AU512947B2 (fr)
BE (1)	BE876297A (fr)
CA (1)	CA1240325A (fr)
CH (1)	CH643553A5 (fr)
CS (1)	CS214796B2 (fr)
DD (1)	DD143613A5 (fr)
DE (1)	DE2919800A1 (fr)
DK (1)	DK159079A (fr)
ES (2)	ES480671A1 (fr)
FI (1)	FI64589C (fr)
FR (1)	FR2434162A1 (fr)
GR (1)	GR72824B (fr)
HU (1)	HU182562B (fr)
IL (1)	IL57297A (fr)
IN (1)	IN153045B (fr)
IT (1)	IT1114222B (fr)
LU (1)	LU81284A1 (fr)
NL (1)	NL172157C (fr)
NO (1)	NO791648L (fr)
NZ (1)	NZ190465A (fr)
PH (1)	PH14802A (fr)
PL (2)	PL121158B1 (fr)
PT (1)	PT69622A (fr)
SE (1)	SE439306B (fr)
YU (2)	YU115279A (fr)
ZA (1)	ZA792390B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4607034A (en) *	1979-10-29	1986-08-19	Mitsubishi Yuka Pharmaceutical Co., Ltd.	Quinazoline derivatives and pharmaceutical composition thereof
JPS5962766U (ja) *	1982-06-30	1984-04-25	守田　智	小動物用給水器
GB8414518D0 (en) *	1984-06-07	1984-07-11	Pfizer Ltd	Therapeutic agents
US5801195A (en) *	1994-12-30	1998-09-01	Celgene Corporation	Immunotherapeutic aryl amides
US6248888B1 (en)	1997-11-14	2001-06-19	Teva Pharmaceutical Industries Ltd.	Process for the preparation of terazosin hydrochloride dihydrate
KR20030069218A (ko) *	2001-01-18	2003-08-25	다케다 야쿠힌 고교 가부시키가이샤	벤질피페리딘 화합물의 제조 방법
US6746460B2 (en) *	2002-08-07	2004-06-08	Satiety, Inc.	Intra-gastric fastening devices
MXPA06005019A (es) *	2003-11-03	2006-07-06	Warner Lambert Co	Nuevos inhibidores de la recaptacion de norpinefrina para el tratamiento de transtornos del sistema nervioso central.
CL2007002958A1 (es) *	2006-10-12	2008-05-09	Epix Delaware Inc	Compuestos derivados de heteroaril-carboxamida, antagonistas del receptor de quimioquina; composicion farmaceutica; y uso para el tratamiento o prevencion de enfermedades tales como rechazo de transplante de organos, artritis reumatoidea, lupus, entr
WO2008122776A2 (fr) *	2007-04-04	2008-10-16	Cipla Limited	Procédé de préparation de l'erlotinib et de ses sels pharmaceutiquement acceptables
KR20100102646A (ko) *	2007-12-11	2010-09-24	가부시키가이샤 사이토파스파인더	카르복스아미드 화합물 및 케모카인 수용체 길항제로서의 이의 용도
BRPI0922010A2 (pt) *	2008-11-14	2015-12-15	Hoffmann La Roche	dervivados de quinazolina como antagonistas receptores de nk3

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1156973A (en) *	1965-07-06	1969-07-02		Quinazoline Derivatives
US3511836A (en) *	1967-12-13	1970-05-12	Pfizer & Co C	2,4,6,7-tetra substituted quinazolines
FR2321890A1 (fr) *	1975-08-26	1977-03-25	Synthelabo	Nouveaux derives de la quinazoline, leurs sels, leur preparation et les medicaments qui en renferment
DK140695C (da) *	1976-05-07	1980-05-12	Synthelabo	Analogifremgangsmaade til fremstilling af 2,4-diamino-6,7-dimethoxyquinazolinderivater eller syreadditionssalte heraf

1979
- 1979-04-18 DK DK159079A patent/DK159079A/da not_active IP Right Cessation
- 1979-05-14 US US06/038,509 patent/US4243666A/en not_active Expired - Lifetime
- 1979-05-16 NZ NZ190465A patent/NZ190465A/xx unknown
- 1979-05-16 AR AR276536A patent/AR223487A1/es active
- 1979-05-16 IN IN337/DEL/79A patent/IN153045B/en unknown
- 1979-05-16 PL PL1979223844A patent/PL121158B1/pl unknown
- 1979-05-16 IT IT22720/79A patent/IT1114222B/it active
- 1979-05-16 GR GR59104A patent/GR72824B/el unknown
- 1979-05-16 NL NLAANVRAGE7903853,A patent/NL172157C/xx not_active IP Right Cessation
- 1979-05-16 NO NO791648A patent/NO791648L/no unknown
- 1979-05-16 PL PL1979215626A patent/PL120651B1/pl unknown
- 1979-05-16 PH PH22500A patent/PH14802A/en unknown
- 1979-05-16 AT AT0363379A patent/ATA363379A/de not_active IP Right Cessation
- 1979-05-16 FI FI791562A patent/FI64589C/fi not_active IP Right Cessation
- 1979-05-16 CS CS793372A patent/CS214796B2/cs unknown
- 1979-05-16 IL IL57297A patent/IL57297A/xx unknown
- 1979-05-16 AU AU47101/79A patent/AU512947B2/en not_active Ceased
- 1979-05-16 BE BE0/195197A patent/BE876297A/fr unknown
- 1979-05-16 YU YU01152/79A patent/YU115279A/xx unknown
- 1979-05-16 DE DE19792919800 patent/DE2919800A1/de not_active Ceased
- 1979-05-17 LU LU81284A patent/LU81284A1/fr unknown
- 1979-05-17 SE SE7904358A patent/SE439306B/sv not_active IP Right Cessation
- 1979-05-17 HU HU79PI678A patent/HU182562B/hu unknown
- 1979-05-17 CH CH459879A patent/CH643553A5/de not_active IP Right Cessation
- 1979-05-17 JP JP6100079A patent/JPS554370A/ja active Granted
- 1979-05-17 CA CA000327839A patent/CA1240325A/fr not_active Expired
- 1979-05-17 FR FR7912635A patent/FR2434162A1/fr active Granted
- 1979-05-17 PT PT69622A patent/PT69622A/pt unknown
- 1979-05-17 ES ES480671A patent/ES480671A1/es not_active Expired
- 1979-05-17 ZA ZA792390A patent/ZA792390B/xx unknown
- 1979-05-18 DD DD79213010A patent/DD143613A5/de unknown
1980
- 1980-02-01 ES ES488210A patent/ES8101584A1/es not_active Expired
- 1980-10-28 AR AR283021A patent/AR224784A1/es active
1982
- 1982-11-16 YU YU02563/82A patent/YU256382A/xx unknown

Also Published As

Publication number	Publication date
IT1114222B (it)	1986-01-27
GR72824B (fr)	1983-12-06
CS214796B2 (en)	1982-05-28
IT7922720A0 (it)	1979-05-16
HU182562B (en)	1984-02-28
PL120651B1 (en)	1982-03-31
AU4710179A (en)	1979-11-22
SE439306B (sv)	1985-06-10
DE2919800A1 (de)	1979-11-22
AU512947B2 (en)	1980-11-06
PL215626A1 (fr)	1980-08-25
NL172157B (nl)	1983-02-16
ZA792390B (en)	1980-07-30
PL223844A1 (fr)	1981-01-02
JPS5623992B2 (fr)	1981-06-03
YU256382A (en)	1983-04-30
ES480671A1 (es)	1980-08-16
YU115279A (en)	1983-04-30
AR223487A1 (es)	1981-08-31
ES488210A0 (es)	1980-12-16
NO791648L (no)	1979-11-20
DK159079A (da)	1979-11-19
CH643553A5 (de)	1984-06-15
PL121158B1 (en)	1982-04-30
IL57297A (en)	1983-02-23
US4243666A (en)	1981-01-06
AR224784A1 (es)	1982-01-15
NZ190465A (en)	1981-05-01
LU81284A1 (fr)	1980-12-16
NL7903853A (nl)	1979-11-20
FR2434162A1 (fr)	1980-03-21
BE876297A (fr)	1979-11-16
JPS554370A (en)	1980-01-12
ATA363379A (de)	1983-05-15
FI64589C (fi)	1983-12-12
PT69622A (en)	1979-06-01
CA1240325A (fr)	1988-08-09
NL172157C (nl)	1983-07-18
ES8101584A1 (es)	1980-12-16
IN153045B (fr)	1984-05-26
FI64589B (fi)	1983-08-31
PH14802A (en)	1981-12-14
FI791562A7 (fi)	1979-11-19
IL57297A0 (en)	1979-09-30
FR2434162B1 (fr)	1983-04-22
SE7904358L (sv)	1979-11-19

Publication	Publication Date	Title
AT363096B (de)	1981-07-10	Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen
DE69103206T2 (de)	1995-03-09	Neue Derivate des Aminopiperidins, Aminopyrrolidins und des Aminoperhydroazepins, Verfahren zur Herstellung und diese enthaltende Arzneimittel.
DE1795769C3 (de)	1978-11-02	6,7,8,9-Tetrahydro-2H-pyrido [Ua] pyrimidinderivate, deren Salze mit Säuren und quaternäre Methosalze, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
DE69611788T2 (de)	2001-08-02	Diphenylmethylenpiperidin-derivate
DE68918609T2 (de)	1995-05-04	Piperidinoalkyl-Derivate von Carbonsäure-Amiden.
CH617938A5 (fr)	1980-06-30
DD273833A5 (de)	1989-11-29	N 9 - cyclopentylsubstituierte adeninderivate
DE2530894A1 (de)	1976-02-05	Chinanzolinderivate
CH648553A5 (de)	1985-03-29	Neue 3,4-dihydro-5h-2,3-benzodiazepin-derivate und verfahren zur herstellung derselben.
CH637130A5 (de)	1983-07-15	Chinazolin-derivate, verfahren zu ihrer herstellung und verwendung dieser derivate in arzneimitteln.
EP0000220B1 (fr)	1981-04-29	Dihydrouraciles, procédé pour leur préparation et médicaments les contenant
DE69811556T2 (de)	2003-08-28	Chinoline und Chinazoline Verbindungen und ihre therapeutische Anwendung
DE2363052A1 (de)	1974-07-11	3-phenyl-3-aminoalkyl-2,6-dioxo-tetraund -hexahydropyridine, verfahren zu ihrer herstellung und ihre verwendung in pharmazeutischen zubereitungen
DE2919800A1 (de)	1979-11-22	4-amino-2-piperidinochinazolin-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel
DE2847621A1 (de)	1979-05-17	Phthalazin-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel
DE68916979T2 (de)	1994-12-15	Alkylen-diamine.
EP0090369B1 (fr)	1986-01-08	Dérivés de l'acide salicylique, procédé pour leur préparation, préparations pharmaceutiques à base des composés et leur application
DE2362754C2 (de)	1985-11-21	Cyclopropylalkylaminoreste enthaltende Oxazolinverbindungen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DE69014930T2 (de)	1995-05-18	Aralkylamin-Verbindungen.
EP0110869A1 (fr)	1984-06-13	Dérivés d'amide thiénylacétique, sels d'addition pharmaceutiquement acceptables et procédé pour leur préparation
EP0233483B1 (fr)	1991-04-03	Pyrrolo[1,2-a][4,1]benzoxazépines, procédé pour leur préparation, compositions pharmaceutiques contenant ces composés et application therapeutique
CH663616A5 (de)	1987-12-31	1,4-dihydropyridin-derivate und sie enthaltende pharmazeutische zubereitungen.
DE2107871C3 (fr)	1974-02-28
DE69200840T2 (de)	1995-06-29	Harnstoff- und Thioharnstoffderivate, Herstellung und therapeutische Verwendung.
DE2643384A1 (de)	1977-06-02	Neue 5,6-dihydropyrimidin-4(3h)-onderivate, verfahren zu ihrer herstellung und ihre verwendung als wirkstoff in pharmazeutischen praeparaten