CH637131A5 - 4-amino-2-piperidino-chinazolin-derivate, verfahren zu ihrer herstellung und verwendung solcher derivate in arzneimitteln. - Google Patents

4-amino-2-piperidino-chinazolin-derivate, verfahren zu ihrer herstellung und verwendung solcher derivate in arzneimitteln. Download PDF

Info

Publication number: CH637131A5
Authority: CH; Switzerland
Prior art keywords: formula; lower alkyl; compounds; prot; group
Prior art date: 1977-11-16

Application number

CH1175578A

Other languages

German (de)

English (en)

Inventor

Simon Fraser Campbell

John Christopher Danilewicz

Colin William Greengrass

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.)

1977-11-16

Filing date

1978-11-15

Publication date

1983-07-15

1978-11-15 Application filed by Pfizer filed Critical Pfizer

1983-07-15 Publication of CH637131A5 publication Critical patent/CH637131A5/de

Links

238000000034 method Methods 0.000 title claims description 10
238000004519 manufacturing process Methods 0.000 title claims 2
229940126601 medicinal product Drugs 0.000 title claims 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 72
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 46
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 43
150000001875 compounds Chemical class 0.000 claims description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
239000000243 solution Substances 0.000 claims description 32
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
239000002904 solvent Substances 0.000 claims description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
239000000047 product Substances 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
239000000725 suspension Substances 0.000 claims description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 12
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 12
238000010992 reflux Methods 0.000 claims description 12
-1 X -OCH2CH2OR1 Chemical group 0.000 claims description 11
239000002026 chloroform extract Substances 0.000 claims description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
150000003053 piperidines Chemical class 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
239000000543 intermediate Substances 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
239000012279 sodium borohydride Substances 0.000 claims description 5
229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
206010020772 Hypertension Diseases 0.000 claims description 4
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 4
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 4
238000001953 recrystallisation Methods 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
VAIHBHWKPBXNLR-UHFFFAOYSA-N 2-piperidin-4-yloxyethanol Chemical compound OCCOC1CCNCC1 VAIHBHWKPBXNLR-UHFFFAOYSA-N 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
230000003276 anti-hypertensive effect Effects 0.000 claims description 2
239000012043 crude product Substances 0.000 claims description 2
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 19
239000001257 hydrogen Substances 0.000 claims 7
125000003545 alkoxy group Chemical group 0.000 claims 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
229910052736 halogen Inorganic materials 0.000 claims 5
150000002367 halogens Chemical class 0.000 claims 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
239000004480 active ingredient Substances 0.000 claims 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
229910052794 bromium Chemical group 0.000 claims 4
229910052801 chlorine Inorganic materials 0.000 claims 4
239000000460 chlorine Substances 0.000 claims 4
150000002431 hydrogen Chemical group 0.000 claims 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
239000000126 substance Substances 0.000 claims 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
230000002378 acidificating effect Effects 0.000 claims 3
125000004432 carbon atom Chemical group C* 0.000 claims 3
125000001309 chloro group Chemical group Cl* 0.000 claims 3
238000007796 conventional method Methods 0.000 claims 3
229940079593 drug Drugs 0.000 claims 3
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
229910019142 PO4 Inorganic materials 0.000 claims 2
239000002585 base Substances 0.000 claims 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
239000002775 capsule Substances 0.000 claims 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
239000003085 diluting agent Substances 0.000 claims 2
239000000546 pharmaceutical excipient Substances 0.000 claims 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
239000010452 phosphate Substances 0.000 claims 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 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 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
241000282472 Canis lupus familiaris Species 0.000 claims 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 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 claims 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 claims 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 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 claims 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 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 claims 1
239000012448 Lithium borohydride Substances 0.000 claims 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
229920002472 Starch Polymers 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
150000001450 anions Chemical class 0.000 claims 1
239000007864 aqueous solution Substances 0.000 claims 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 claims 1
230000036772 blood pressure Effects 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
238000007385 chemical modification Methods 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
229940001468 citrate Drugs 0.000 claims 1
239000003086 colorant Substances 0.000 claims 1
238000010511 deprotection reaction Methods 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
230000002526 effect on cardiovascular system Effects 0.000 claims 1
239000004744 fabric Substances 0.000 claims 1
238000001914 filtration Methods 0.000 claims 1
239000000796 flavoring agent Substances 0.000 claims 1
235000019634 flavors Nutrition 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
150000008423 fluorobenzenes Chemical class 0.000 claims 1
238000001640 fractional crystallisation Methods 0.000 claims 1
229940050411 fumarate Drugs 0.000 claims 1
229940050410 gluconate Drugs 0.000 claims 1
239000008103 glucose Substances 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
230000001631 hypertensive effect Effects 0.000 claims 1
238000001990 intravenous administration Methods 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
229940001447 lactate Drugs 0.000 claims 1
239000008101 lactose Substances 0.000 claims 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
238000002156 mixing Methods 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
238000007911 parenteral administration Methods 0.000 claims 1
150000002989 phenols Chemical class 0.000 claims 1
238000000053 physical method Methods 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
239000002243 precursor Substances 0.000 claims 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
230000002441 reversible effect Effects 0.000 claims 1
210000002966 serum Anatomy 0.000 claims 1
238000011699 spontaneously hypertensive rat Methods 0.000 claims 1
239000008107 starch Substances 0.000 claims 1
235000019698 starch Nutrition 0.000 claims 1
125000005415 substituted alkoxy group Chemical group 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
229940095064 tartrate Drugs 0.000 claims 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
238000004458 analytical method Methods 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
239000008346 aqueous phase Substances 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
239000012312 sodium hydride Substances 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000007832 Na2SO4 Substances 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
KZPIFQYDCVCSDS-UHFFFAOYSA-N 1-(4-hydroxypiperidin-1-yl)ethanone Chemical compound CC(=O)N1CCC(O)CC1 KZPIFQYDCVCSDS-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000002480 mineral oil Substances 0.000 description 7
235000010446 mineral oil Nutrition 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
NJCJXKIBQLPVPM-UHFFFAOYSA-N 1-[4-(2-hydroxyethoxy)piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCC(OCCO)CC1 NJCJXKIBQLPVPM-UHFFFAOYSA-N 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
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 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
238000003756 stirring Methods 0.000 description 4
LLMZNCCAWHTARU-UHFFFAOYSA-N 1-[4-(2,2-diethoxyethoxy)piperidin-1-yl]ethanone Chemical compound CCOC(OCC)COC1CCN(C(C)=O)CC1 LLMZNCCAWHTARU-UHFFFAOYSA-N 0.000 description 3
VJTNGFWRDWFHIT-UHFFFAOYSA-N 4-[2-(1-acetylpiperidin-4-yl)oxyethoxy]benzamide Chemical compound C1CN(C(=O)C)CCC1OCCOC1=CC=C(C(N)=O)C=C1 VJTNGFWRDWFHIT-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000004611 spectroscopical analysis Methods 0.000 description 3
GRJRGMAVNWPXLX-UHFFFAOYSA-N 2-(2,6-dimethoxyphenoxy)ethyl methanesulfonate Chemical compound COC1=CC=CC(OC)=C1OCCOS(C)(=O)=O GRJRGMAVNWPXLX-UHFFFAOYSA-N 0.000 description 2
LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 2
NVESPAGIUWPFCX-UHFFFAOYSA-N 4-(2-ethoxypropoxy)piperidine Chemical compound CCOC(C)COC1CCNCC1 NVESPAGIUWPFCX-UHFFFAOYSA-N 0.000 description 2
KTXVOCUROHMWQP-UHFFFAOYSA-N 4-(2-methoxyethoxy)piperidine Chemical compound COCCOC1CCNCC1 KTXVOCUROHMWQP-UHFFFAOYSA-N 0.000 description 2
MNRJBWWZVOCYSN-UHFFFAOYSA-N 4-(2-methoxypropoxy)piperidine Chemical compound COC(C)COC1CCNCC1 MNRJBWWZVOCYSN-UHFFFAOYSA-N 0.000 description 2
LCBWBBJCOKLDQY-UHFFFAOYSA-N 4-(2-phenoxypropoxy)piperidine Chemical compound C=1C=CC=CC=1OC(C)COC1CCNCC1 LCBWBBJCOKLDQY-UHFFFAOYSA-N 0.000 description 2
JSVPJTAWUXNRAD-UHFFFAOYSA-N 4-(2-piperidin-4-yloxyethoxy)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OCCOC1CCNCC1 JSVPJTAWUXNRAD-UHFFFAOYSA-N 0.000 description 2
WNZCEVHUMWODJS-UHFFFAOYSA-N 4-[2-(4-fluorophenoxy)ethoxy]piperidine Chemical compound C1=CC(F)=CC=C1OCCOC1CCNCC1 WNZCEVHUMWODJS-UHFFFAOYSA-N 0.000 description 2
QXSAKPUBHTZHKW-UHFFFAOYSA-N 4-hydroxybenzamide Chemical compound NC(=O)C1=CC=C(O)C=C1 QXSAKPUBHTZHKW-UHFFFAOYSA-N 0.000 description 2
XGMQXALOAFFCRD-UHFFFAOYSA-N 6,7-dimethoxy-2-[4-(2-methoxypropoxy)piperidin-1-yl]quinazolin-4-amine;hydrochloride Chemical compound Cl.C1CC(OCC(C)OC)CCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 XGMQXALOAFFCRD-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
238000011097 chromatography purification Methods 0.000 description 2
KAQVFEITQMBSEF-UHFFFAOYSA-N cyclopentyl methanesulfonate Chemical compound CS(=O)(=O)OC1CCCC1 KAQVFEITQMBSEF-UHFFFAOYSA-N 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
150000003246 quinazolines Chemical class 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
ZNOFYDOYQNIMRS-UHFFFAOYSA-N 1-[4-(2-hydroxypropoxy)piperidin-1-yl]ethanone Chemical compound CC(O)COC1CCN(C(C)=O)CC1 ZNOFYDOYQNIMRS-UHFFFAOYSA-N 0.000 description 1
HKHAOLJNVGPHEM-UHFFFAOYSA-N 1-[4-(2-methoxypropoxy)piperidin-1-yl]ethanone Chemical compound COC(C)COC1CCN(C(C)=O)CC1 HKHAOLJNVGPHEM-UHFFFAOYSA-N 0.000 description 1
NSSAWDSENKKBBD-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethoxyphenoxy)ethoxy]piperidin-1-yl]ethanone Chemical compound COC1=CC=CC(OC)=C1OCCOC1CCN(C(C)=O)CC1 NSSAWDSENKKBBD-UHFFFAOYSA-N 0.000 description 1
KPRSMNXEKIFCMX-UHFFFAOYSA-N 1-piperidin-4-yloxypropan-2-ol Chemical compound CC(O)COC1CCNCC1 KPRSMNXEKIFCMX-UHFFFAOYSA-N 0.000 description 1
XFZDXZBPRADNBD-UHFFFAOYSA-N 2-(2,6-dimethoxyphenoxy)ethanol Chemical compound COC1=CC=CC(OC)=C1OCCO XFZDXZBPRADNBD-UHFFFAOYSA-N 0.000 description 1
YQMVHLTZKBEFFQ-UHFFFAOYSA-N 2-[4-(2-ethoxyethoxy)piperidin-1-yl]-6,7-dimethoxyquinazolin-4-amine;hydrochloride Chemical compound Cl.C1CC(OCCOCC)CCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 YQMVHLTZKBEFFQ-UHFFFAOYSA-N 0.000 description 1
OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
IJDWIEIJKIGROU-UHFFFAOYSA-N 4-(2-cyclopentyloxyethoxy)piperidine Chemical compound C1CCCC1OCCOC1CCNCC1 IJDWIEIJKIGROU-UHFFFAOYSA-N 0.000 description 1
JSCHXBPVXYQFGH-UHFFFAOYSA-N 4-(2-cyclopentyloxyethoxy)piperidine;hydrochloride Chemical compound Cl.C1CCCC1OCCOC1CCNCC1 JSCHXBPVXYQFGH-UHFFFAOYSA-N 0.000 description 1
YUAFBJXCTHYOSJ-UHFFFAOYSA-N 4-(2-ethoxyethoxy)piperidine Chemical compound CCOCCOC1CCNCC1 YUAFBJXCTHYOSJ-UHFFFAOYSA-N 0.000 description 1
QFXUVUTWGVBESE-UHFFFAOYSA-N 4-(2-propan-2-yloxyethoxy)piperidine Chemical compound CC(C)OCCOC1CCNCC1 QFXUVUTWGVBESE-UHFFFAOYSA-N 0.000 description 1
QQAISUUBGKFFIS-UHFFFAOYSA-N 4-[2-(2,6-dimethoxyphenoxy)ethoxy]piperidine Chemical compound COC1=CC=CC(OC)=C1OCCOC1CCNCC1 QQAISUUBGKFFIS-UHFFFAOYSA-N 0.000 description 1
LVDFUDDBYMTMNS-UHFFFAOYSA-N 4-[2-(2,6-dimethoxyphenoxy)ethoxy]piperidine;hydrochloride Chemical compound Cl.COC1=CC=CC(OC)=C1OCCOC1CCNCC1 LVDFUDDBYMTMNS-UHFFFAOYSA-N 0.000 description 1
RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
125000003047 N-acetyl group Chemical group 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000010828 elution Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
RLXDCJUIXHSXQD-UHFFFAOYSA-N oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O.OC(=O)C(O)=O RLXDCJUIXHSXQD-UHFFFAOYSA-N 0.000 description 1
SMPAPEKFGLKOIC-UHFFFAOYSA-N oxolane;hydrochloride Chemical compound Cl.C1CCOC1 SMPAPEKFGLKOIC-UHFFFAOYSA-N 0.000 description 1
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
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 description 1
239000002244 precipitate Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 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
- C07D211/40—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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)

CH1175578A 1977-11-16 1978-11-15 4-amino-2-piperidino-chinazolin-derivate, verfahren zu ihrer herstellung und verwendung solcher derivate in arzneimitteln. CH637131A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB4758377		1977-11-16
GB7844533A GB2010824B (en)	1977-11-16	1978-11-15	Therapeutic agents

Publications (1)

Publication Number	Publication Date
CH637131A5 true CH637131A5 (de)	1983-07-15

Family

ID=26266083

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1175578A CH637131A5 (de)	1977-11-16	1978-11-15	4-amino-2-piperidino-chinazolin-derivate, verfahren zu ihrer herstellung und verwendung solcher derivate in arzneimitteln.

Country Status (12)

Country	Link
JP (1)	JPS5481282A (fr)
AT (1)	AT365183B (fr)
AU (1)	AU509348B2 (fr)
BE (1)	BE872023A (fr)
CA (1)	CA1088068A (fr)
CH (1)	CH637131A5 (fr)
DE (1)	DE2849392A1 (fr)
FR (1)	FR2409267A1 (fr)
GB (1)	GB2010824B (fr)
LU (1)	LU80531A1 (fr)
NL (1)	NL174646C (fr)
SE (1)	SE7811770L (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE800178L (en) *	1979-01-31	1980-07-31	Pfizer Ltd	Derivatives of 4-amino-2-piperidinoquinazoline
FR2514353A2 (fr) *	1980-04-28	1983-04-15	Synthelabo	Derives de piperidine et leur application en therapeutique
FR2481278A1 (fr) *	1980-04-28	1981-10-30	Synthelabo	Nouveaux derives de piperidine, leur procede de preparation et leur application en therapeutique
JPS62212385A (ja) *	1986-03-13	1987-09-18	Kotobuki Seiyaku Kk	キナゾリン誘導体並びに血圧降下剤及びその製法

1978
- 1978-10-24 CA CA314,082A patent/CA1088068A/fr not_active Expired
- 1978-11-14 AU AU41576/78A patent/AU509348B2/en not_active Expired
- 1978-11-14 NL NLAANVRAGE7811236,A patent/NL174646C/xx not_active IP Right Cessation
- 1978-11-14 BE BE191743A patent/BE872023A/fr not_active IP Right Cessation
- 1978-11-14 SE SE7811770A patent/SE7811770L/xx unknown
- 1978-11-14 DE DE19782849392 patent/DE2849392A1/de not_active Withdrawn
- 1978-11-15 CH CH1175578A patent/CH637131A5/de not_active IP Right Cessation
- 1978-11-15 JP JP14094678A patent/JPS5481282A/ja active Granted
- 1978-11-15 LU LU80531A patent/LU80531A1/fr unknown
- 1978-11-15 AT AT0816678A patent/AT365183B/de active
- 1978-11-15 FR FR7832235A patent/FR2409267A1/fr active Granted
- 1978-11-15 GB GB7844533A patent/GB2010824B/en not_active Expired

Also Published As

Publication number	Publication date
LU80531A1 (fr)	1980-06-05
FR2409267B1 (fr)	1981-02-27
BE872023A (fr)	1979-05-14
DE2849392A1 (de)	1979-05-23
FR2409267A1 (fr)	1979-06-15
GB2010824B (en)	1982-06-16
GB2010824A (en)	1979-07-04
JPS5623991B2 (fr)	1981-06-03
NL7811236A (nl)	1979-05-18
AU509348B2 (en)	1980-05-08
CA1088068A (fr)	1980-10-21
AT365183B (de)	1981-12-28
NL174646B (nl)	1984-02-16
AU4157678A (en)	1979-05-24
NL174646C (nl)	1984-07-16
SE7811770L (sv)	1979-05-17
JPS5481282A (en)	1979-06-28
ATA816678A (de)	1981-05-15

Legal Events

Date	Code	Title	Description
1985-07-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE3689836T2 (de)	1994-09-22	Zyklische aminabkömmlinge.
DE69815008T2 (de)	2004-04-01	Alfa-substituierte Phenylpropionsäurederivate und diese enthaltende Arzneimittel
DE3874358T2 (de)	1993-01-28	4-(3h)-chinazolinon-derivate, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen.
DE2624693A1 (de)	1977-07-14	Isochromanderivate und verfahren zu deren herstellung
EP0025192A2 (fr)	1981-03-18	Acides oxiranne-carboxyliques substitués, procédé pour leur préparation, leur utilisation et médicaments les contenant
DE3788507T2 (de)	1994-05-19	Substituierte 1H-Imidazole.
DE2830884C2 (fr)	1990-01-11
DD223452A5 (de)	1985-06-12	Verfahren zur herstellung von piperidinochinazolinen
DE2410938A1 (de)	1974-09-19	Chinazolinderivate und diese enthaltende arzneimittel
DD202023A5 (de)	1983-08-24	Verfahren zur herstellung von in 5-stellung substituierten 5,10-dihxdro-11h-dibenzo (b,e) (1,4) diazepin-11-onen
DE3813531A1 (de)	1988-11-10	Neue 2-aminoalkyl-4-benzyl-1-(2h)-phthalazinon-derivate
DE3315797A1 (de)	1984-10-31	Substituierte phenyl-2-(1h)-pyrimidinone, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen
DE69131057T2 (de)	1999-09-09	3-[1,Thiazolidinylbutyl-4-piperazinyl]-1H-Indazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Medikamente
DE2847623C2 (de)	1983-06-01	4-Amino-2-(piperazin-1-yl oder homopiperazin-1-yl)-chinazolinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
CH651302A5 (de)	1985-09-13	In 6-stellung substituierte 6h-dibenzo-(b,d)-pyranderivate und verfahren zu ihrer herstellung.
DE69219801T2 (de)	1997-11-27	9-Aminotetrahydroakridinederivate und verwandte Derivate, Verfahren zur ihrer Herstellung und ihre Anwendung als Arzneimittel
DE69500329T2 (de)	1997-10-30	Neue Triazol-Verbindung mit fungizider Wirkung, deren Herstellung und Verwendung
EP0072960A2 (fr)	1983-03-02	Composés 1,5-diphénylpyrazolin-3-one, ainsi qu'un procédé et produits intermédiaires pour leur fabrication et médicaments contenant ces composés
DE69629931T2 (de)	2004-07-29	1-(hetero)aryl-4-(kondensiertes thiazol-2-ylalkyl)-piperazin derivate, deren herstellung und deren verwendung in der behandlung von 5-ht1a-rezeptor vermittelten krankheiten
DE2849392A1 (de)	1979-05-23	4-amino-2-piperidino-chinazolin- derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel
DE1470055A1 (de)	1969-07-17	Verfahren zur Herstellung von Piperidinderivaten
DE19735410A1 (de)	1999-02-18	2-{3-[4-(2-t-Butyl-6-trifluormethylpyrimidin-4-yl)piperazin-1-yl]propylmercapto}pyrimidin-4-ol-fumarat
DE3003323A1 (de)	1980-08-14	4-amino-2-piperidinochinazolin-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel
EP0241654B1 (fr)	1991-04-17	Esters d'hydroxyindole
EP0212216A1 (fr)	1987-03-04	Dérivés de la dihydroquinolinone, procédés pour leur préparation, médicaments les contenant et l'application de ceux-ci ainsi que produits intermédiaires pour leur préparation