LU80461A1 - Derives de quinazoline,leur procede de production et composition pharmaceutique les contenant - Google Patents

Derives de quinazoline,leur procede de production et composition pharmaceutique les contenant Download PDF

Info

Publication number: LU80461A1
Authority: LU; Luxembourg
Prior art keywords: group; formula; hydrogen atom; lower alkyl; alkyl group
Prior art date: 1977-11-03

Application number

LU80461A

Other languages

English (en)

French (fr)

Inventor

J Danilewicz

S Campbell

J Stubbs

A Ham

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.)

1977-11-03

Filing date

1978-10-31

Publication date

1980-05-07

1978-10-31 Application filed by Pfizer filed Critical Pfizer

1980-05-07 Publication of LU80461A1 publication Critical patent/LU80461A1/fr

Links

JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical class N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 title claims description 6
239000008194 pharmaceutical composition Substances 0.000 title description 4
238000004519 manufacturing process Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 45
239000002253 acid Substances 0.000 claims description 19
238000002360 preparation method Methods 0.000 claims description 17
238000000034 method Methods 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims description 6
101150113676 chr1 gene Proteins 0.000 claims description 6
230000008569 process Effects 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 claims description 2
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 claims description 2
230000009466 transformation Effects 0.000 claims 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 1
101100295738 Gallus gallus COR3 gene Proteins 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
-1 iodhydra-tes Chemical class 0.000 description 19
239000000243 solution Substances 0.000 description 16
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 15
239000000203 mixture Substances 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000004458 analytical method Methods 0.000 description 11
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000003814 drug Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
229940079593 drug Drugs 0.000 description 7
239000003921 oil Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
230000008602 contraction Effects 0.000 description 5
239000000284 extract Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
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 5
239000007858 starting material Substances 0.000 description 5
241000282472 Canis lupus familiaris Species 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000000047 product Substances 0.000 description 4
150000003246 quinazolines Chemical class 0.000 description 4
238000010992 reflux Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
210000005240 left ventricle Anatomy 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
150000003254 radicals Chemical group 0.000 description 3
239000000376 reactant Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
LLLHRNQLGUOJHP-UHFFFAOYSA-N 4-chloro-6,7-dimethoxyquinazoline Chemical compound C1=NC(Cl)=C2C=C(OC)C(OC)=CC2=N1 LLLHRNQLGUOJHP-UHFFFAOYSA-N 0.000 description 2
208000020446 Cardiac disease Diseases 0.000 description 2
206010019280 Heart failures Diseases 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012458 free base Substances 0.000 description 2
210000002837 heart atrium Anatomy 0.000 description 2
208000019622 heart disease Diseases 0.000 description 2
230000000297 inotrophic effect Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
230000002107 myocardial effect Effects 0.000 description 2
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
150000003053 piperidines Chemical class 0.000 description 2
230000009090 positive inotropic effect Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000003449 preventive effect Effects 0.000 description 2
230000004044 response Effects 0.000 description 2
239000000523 sample Substances 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
NZKFUBQRAWPZJP-BXKLGIMVSA-N (2s,3r,4s,5s,6r)-4-amino-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,5s,6r)-3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol;sulfuric acid Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N.N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NZKFUBQRAWPZJP-BXKLGIMVSA-N 0.000 description 1
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 1
OTYCRQJZOXMPSK-UHFFFAOYSA-N 1-phenyl-n-(piperidin-4-ylmethyl)methanimine Chemical compound C1CNCCC1CN=CC1=CC=CC=C1 OTYCRQJZOXMPSK-UHFFFAOYSA-N 0.000 description 1
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 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
102100024167 C-C chemokine receptor type 3 Human genes 0.000 description 1
101710149862 C-C chemokine receptor type 3 Proteins 0.000 description 1
YQZYLRPENOUEOG-UHFFFAOYSA-N CNCCC1=CC=NC=C1.NCCC1=CC=NC=C1 Chemical compound CNCCC1=CC=NC=C1.NCCC1=CC=NC=C1 YQZYLRPENOUEOG-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
206010007556 Cardiac failure acute Diseases 0.000 description 1
206010007559 Cardiac failure congestive Diseases 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 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
241000282412 Homo Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-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
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
OWSAUAOACLOTFG-UHFFFAOYSA-N [1-(6,7-dimethoxyquinazolin-4-yl)piperidin-4-yl]methanamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N1CCC(CN)CC1 OWSAUAOACLOTFG-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000003637 basic solution Substances 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
230000015572 biosynthetic process Effects 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
239000000496 cardiotonic agent Substances 0.000 description 1
238000007385 chemical modification Methods 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
230000002057 chronotropic effect Effects 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000007547 defect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000002513 implantation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229960001317 isoprenaline Drugs 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000155 melt 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
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
TYQJCPFOIMPJLQ-UHFFFAOYSA-N n-(2-pyridin-4-ylethyl)propan-2-amine Chemical compound CC(C)NCCC1=CC=NC=C1 TYQJCPFOIMPJLQ-UHFFFAOYSA-N 0.000 description 1
MZCVTBJXTMEQLJ-UHFFFAOYSA-N n-(pyridin-4-ylmethyl)acetamide Chemical compound CC(=O)NCC1=CC=NC=C1 MZCVTBJXTMEQLJ-UHFFFAOYSA-N 0.000 description 1
DNBWGFKLIBQQSL-UHFFFAOYSA-N n-methyl-1-pyridin-4-ylmethanamine Chemical compound CNCC1=CC=NC=C1 DNBWGFKLIBQQSL-UHFFFAOYSA-N 0.000 description 1
PWNSBHKGVZXSAJ-UHFFFAOYSA-N n-methyl-n-(2-pyridin-4-ylethyl)butanamide Chemical compound CCCC(=O)N(C)CCC1=CC=NC=C1 PWNSBHKGVZXSAJ-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
COCLZFOKBPQFPC-UHFFFAOYSA-N oxalic acid;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.OC(=O)C(O)=O.OC(=O)C(O)=O.OC(=O)C(O)=O COCLZFOKBPQFPC-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002304 perfume Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 description 1
235000019100 piperine Nutrition 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
ZDHURYWHEBEGHO-UHFFFAOYSA-N potassiopotassium Chemical compound [K].[K] ZDHURYWHEBEGHO-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
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238000009877 rendering Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
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239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- C07D211/28—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom

Landscapes

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

LU80461A 1977-11-03 1978-10-31 Derives de quinazoline,leur procede de production et composition pharmaceutique les contenant LU80461A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB4566977		1977-11-03
GB4566977		1977-11-03

Publications (1)

Publication Number	Publication Date
LU80461A1 true LU80461A1 (fr)	1980-05-07

Family

ID=10438111

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU80461A LU80461A1 (fr)	1977-11-03	1978-10-31	Derives de quinazoline,leur procede de production et composition pharmaceutique les contenant

Country Status (24)

Country	Link
US (1)	US4188391A (pt)
JP (1)	JPS5498786A (pt)
AR (2)	AR221851A1 (pt)
AT (1)	AT366043B (pt)
AU (1)	AU506317B2 (pt)
BE (1)	BE871769A (pt)
CA (1)	CA1086735A (pt)
CH (1)	CH637130A5 (pt)
DE (1)	DE2847622A1 (pt)
DK (1)	DK488078A (pt)
ES (2)	ES474763A1 (pt)
FI (1)	FI63934C (pt)
FR (1)	FR2407926A1 (pt)
HK (1)	HK94184A (pt)
IE (1)	IE47996B1 (pt)
IL (1)	IL55845A (pt)
IT (1)	IT1101287B (pt)
KE (1)	KE3351A (pt)
LU (1)	LU80461A1 (pt)
MY (1)	MY8500284A (pt)
NL (1)	NL174144C (pt)
PH (1)	PH14693A (pt)
PT (1)	PT68733A (pt)
SE (1)	SE7811323L (pt)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
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US4489075A (en) *	1982-05-15	1984-12-18	Pfizer Inc.	Cyclic sulfonamidoalkyl substituted 4-piperidinoquinazoline cardiac stimulants
JPS61215389A (ja) *	1985-03-20	1986-09-25	Kyowa Hakko Kogyo Co Ltd	キナゾリン誘導体およびそれを含有する強心剤
CA2148260A1 (en) *	1993-09-10	1995-03-16	Yasutaka Takase	Quinazoline cpompounds
US6518423B1 (en)	1996-08-09	2003-02-11	Eisai Co., Ltd.	Benzopiperidine derivatives
JP2009506069A (ja)	2005-08-26	2009-02-12	ブレインセルス，インコーポレイティド	ムスカリン性受容体調節による神経発生
EP2258359A3 (en)	2005-08-26	2011-04-06	Braincells, Inc.	Neurogenesis by muscarinic receptor modulation with sabcomelin
JP2009512711A (ja)	2005-10-21	2009-03-26	ブレインセルス，インコーポレイティド	Ｐｄｅ阻害による神経新生の調節
EP2314289A1 (en)	2005-10-31	2011-04-27	Braincells, Inc.	Gaba receptor mediated modulation of neurogenesis
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
CA2643199A1 (en) *	2006-03-08	2007-09-13	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
AU2007249399A1 (en)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenesis by modulating angiotensin
US20100009983A1 (en) *	2006-05-09	2010-01-14	Braincells, Inc.	5 ht receptor mediated neurogenesis
CA2651862A1 (en)	2006-05-09	2007-11-22	Braincells, Inc.	5 ht receptor mediated neurogenesis
WO2008030651A1 (en) *	2006-09-08	2008-03-13	Braincells, Inc.	Combinations containing a 4-acylaminopyridine derivative
US20100184806A1 (en)	2006-09-19	2010-07-22	Braincells, Inc.	Modulation of neurogenesis by ppar agents
AU2007299920A1 (en) *	2006-09-19	2008-03-27	Braincells, Inc.	PPAR Mediated Modulation of Neurogenesis
EP2074111A2 (en) *	2006-10-06	2009-07-01	Bausch & Lomb Incorporated	Quinolone carboxylic acids, derivatives thereof, processes for its preparation and its use as antibacterial agents
US7632944B2 (en) *	2007-01-24	2009-12-15	Bausch & Lomb Incorporated	Quinolone carboxylic acids, derivatives thereof, and methods of making and using same
US20100216805A1 (en)	2009-02-25	2010-08-26	Braincells, Inc.	Modulation of neurogenesis using d-cycloserine combinations
WO2013106547A1 (en)	2012-01-10	2013-07-18	President And Fellows Of Harvard College	Beta-cell replication promoting compounds and methods of their use
JP7688912B2 (ja) *	2019-03-19	2025-06-05	スティングレイ・セラピューティクス・インコーポレイテッド	キノリンおよびキナゾリン化合物およびその使用方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3812127A (en) *	1966-10-31	1974-05-21	Pfizer	4-(quinolin-4-yl)piperazine-1-carboxylic acid esters
GB1199768A (en) *	1966-10-31	1970-07-22	Pfizer & Co C	Nitrogen Heterocycles and process for their preparation
US3517005A (en) *	1967-10-26	1970-06-23	Pfizer & Co C	Certain 2- and 4-substituted quinazolines
GB1460389A (en) *	1974-07-25	1977-01-06	Pfizer Ltd	4-substituted quinazoline cardiac stimulants

1978
- 1978-10-24 CA CA314,062A patent/CA1086735A/en not_active Expired
- 1978-10-26 US US05/954,931 patent/US4188391A/en not_active Expired - Lifetime
- 1978-10-30 PH PH21751A patent/PH14693A/en unknown
- 1978-10-31 LU LU80461A patent/LU80461A1/fr unknown
- 1978-11-01 DK DK488078A patent/DK488078A/da not_active Application Discontinuation
- 1978-11-01 IL IL55845A patent/IL55845A/xx unknown
- 1978-11-01 AR AR274310A patent/AR221851A1/es active
- 1978-11-01 FI FI783325A patent/FI63934C/fi not_active IP Right Cessation
- 1978-11-01 SE SE7811323A patent/SE7811323L/xx unknown
- 1978-11-01 CH CH1125378A patent/CH637130A5/de not_active IP Right Cessation
- 1978-11-01 NL NLAANVRAGE7810865,A patent/NL174144C/xx not_active IP Right Cessation
- 1978-11-02 IT IT29368/78A patent/IT1101287B/it active
- 1978-11-02 IE IE2165/78A patent/IE47996B1/en unknown
- 1978-11-02 AU AU41277/78A patent/AU506317B2/en not_active Expired
- 1978-11-02 JP JP13569678A patent/JPS5498786A/ja active Granted
- 1978-11-02 AT AT0783878A patent/AT366043B/de not_active IP Right Cessation
- 1978-11-02 DE DE19782847622 patent/DE2847622A1/de not_active Ceased
- 1978-11-02 FR FR7831062A patent/FR2407926A1/fr active Granted
- 1978-11-02 ES ES474763A patent/ES474763A1/es not_active Expired
- 1978-11-02 PT PT68733A patent/PT68733A/pt unknown
- 1978-11-03 BE BE191542A patent/BE871769A/xx not_active IP Right Cessation
1979
- 1979-04-27 ES ES480053A patent/ES480053A1/es not_active Expired
- 1979-11-01 AR AR278733A patent/AR221251A1/es active
1983
- 1983-11-21 KE KE3351A patent/KE3351A/xx unknown
1984
- 1984-11-29 HK HK941/84A patent/HK94184A/xx unknown
1985
- 1985-12-30 MY MY284/85A patent/MY8500284A/xx unknown

Also Published As

Publication number	Publication date
IT7829368A0 (it)	1978-11-02
ES480053A1 (es)	1980-07-16
JPS5498786A (en)	1979-08-03
JPS566428B2 (pt)	1981-02-10
AT366043B (de)	1982-03-10
CH637130A5 (de)	1983-07-15
CA1086735A (en)	1980-09-30
AU506317B2 (en)	1979-12-20
DK488078A (da)	1979-05-04
MY8500284A (en)	1985-12-31
FR2407926B1 (pt)	1982-11-12
IE47996B1 (en)	1984-08-22
HK94184A (en)	1984-12-07
IL55845A (en)	1982-07-30
KE3351A (en)	1983-12-16
PT68733A (en)	1978-12-01
ATA783878A (de)	1981-07-15
AU4127778A (en)	1979-05-17
AR221851A1 (es)	1981-03-31
SE7811323L (sv)	1979-05-04
PH14693A (en)	1981-11-10
FI63934C (fi)	1983-09-12
IL55845A0 (en)	1979-01-31
FI63934B (fi)	1983-05-31
FR2407926A1 (fr)	1979-06-01
DE2847622A1 (de)	1979-05-31
BE871769A (fr)	1979-05-03
IT1101287B (it)	1985-09-28
AR221251A1 (es)	1981-01-15
US4188391A (en)	1980-02-12
NL7810865A (nl)	1979-05-07
FI783325A7 (fi)	1979-05-04
NL174144C (nl)	1984-05-01
NL174144B (nl)	1983-12-01
ES474763A1 (es)	1980-12-16

Publication	Publication Date	Title
LU80461A1 (fr)	1980-05-07	Derives de quinazoline,leur procede de production et composition pharmaceutique les contenant
LU79761A1 (fr)	1980-01-22	Procede de preparation de nouveaux composes de phtalazine et de composition pharmaceutique les contenant
EP0202164B1 (fr)	1989-02-08	Dérivés de (benzoyl-4 pipéridino)-2 phenyl-1 alcanols, leur préparation et leur application en thérapeutique
EP0307303B1 (fr)	1991-12-04	[(Pyrimidinyl-2)-aminoalkyl]-1 pipéridines, leur préparation et leur application en thérapeutique
EP0124476B1 (de)	1988-06-22	Carboxamide, Verfahren zur Herstellung und pharmazeutische Präparate, die diese enthalten
BE898278A (fr)	1984-05-22	Benzoxazines antipsychotiques.
EP0177392A1 (fr)	1986-04-09	Nouvelles (pyridyl-2)-1 pipérazines, leur procédé de préparation et leur application en thérapeutique
EP0037778A1 (fr)	1981-10-14	Benzodioxanne 1,4 méthoxy-2 propanolamines, leur préparation et leur application en tant que médicaments
EP0382637A1 (fr)	1990-08-16	Dérivés de pyrimidinyl-piperazinyl-alkyl azolès avec activité anxiolytique et/ou tranquillisante
LU80458A1 (fr)	1980-05-07	Nouveaux derives de phtalazine,leur procede de production,et composition pharmaceutique les contenant
EP0000299B1 (fr)	1980-11-12	Nouveaux dérivés de benzoyl-2-chloro-4-glycinanilides substitués, leur procédé de préparation et leur application en tant que médicaments.
EP0459887A1 (fr)	1991-12-04	Dérivés N-pyrazolyl-ortho-dialkyl-benzamide doués d'activité anticonvulsivante, procédé de préparation et composition pharmaceutique
EP0360685B1 (fr)	1994-02-02	"[(diarylméthoxy) alcoyl] - 1 pyrrolidines et piperidines, procédés de préparation et médicaments les contenant"
EP0524846A1 (fr)	1993-01-27	Dérivés de 2-(pipéridin-1-y1) éthanol, leur préparation et leur application en thérapeutique
FR2662442A1 (fr)	1991-11-29	Trifluoromethylphenyltetrahydropyridines n-substituees procede pour leur preparation, intermediaires du procede et compositions pharmaceutiques les contenant.
EP0117196A1 (fr)	1984-08-29	Nouveaux dérivés de bétaines n-iminopyridinium, leur préparation et leur application en tant que médicaments
EP0301936A1 (fr)	1989-02-01	Dérivés de pipéridine, leur préparation et leur application en thérapeutique
EP0143016B1 (fr)	1987-07-29	Dérivés de 4-(3-alkynyloxy-2-hydroxy-propyl)-piperazin-1-yl-N-phényl acétamide, leur préparation et leur application en thérapeutique
CA1082716A (fr)	1980-07-29	Procede de preparation de nouveaux derives de 5- thiazole methane amine
EP0487423A1 (fr)	1992-05-27	Nouveaux dérivés de la benzosélénazolinone, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
JPS6399057A (ja)	1988-04-30	グリシン誘導体
EP0037344A1 (fr)	1981-10-07	Amino-alcoxy pyrazoles, procédé pour leur préparation, et médicaments les contenant
EP0294258A1 (fr)	1988-12-07	Dérivés d'hydrazine, procédé d'obtention et compositions pharmaceutiques les contenant
EP0362006A1 (fr)	1990-04-04	Dérivés de quinoléine, leurs procédés de préparation et les médicaments les contenant
JP3096065B2 (ja)	2000-10-10	医薬的に活性な鏡像体