CA1167843A - Derives de 3-(1-piperidinyalkyl)-4h-pyrido [1,2-a]-pyrimidin-4-one - Google Patents

Derives de 3-(1-piperidinyalkyl)-4h-pyrido [1,2-a]-pyrimidin-4-one

Info

Publication number: CA1167843A
Authority: CA; Canada
Prior art keywords: group; parts; lower alkyl; hydrogen; formula
Prior art date: 1980-03-28
Legal status (The legal status 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 status listed.): Expired

Application number

CA000430092A

Other languages

English (en)

Inventor

Ludo E.J. Kennis

Josephus C. Mertens

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Janssen Pharmaceutica NV

Original Assignee

Janssen Pharmaceutica NV

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.)

1980-03-28

Filing date

1983-06-09

Publication date

1984-05-22

1980-09-29 Priority claimed from US06/191,632 external-priority patent/US4342870A/en

1983-06-09 Application filed by Janssen Pharmaceutica NV filed Critical Janssen Pharmaceutica NV

1983-06-09 Priority to CA000430092A priority Critical patent/CA1167843A/fr

1984-05-22 Application granted granted Critical

1984-05-22 Publication of CA1167843A publication Critical patent/CA1167843A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 49
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 8
-1 nitro, amino Chemical group 0.000 claims description 39
238000000034 method Methods 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 22
239000011541 reaction mixture Substances 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 13
238000010992 reflux Methods 0.000 claims description 11
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
125000001475 halogen functional group Chemical group 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
125000004185 ester group Chemical group 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
NYJWYCAHJRGKMI-UHFFFAOYSA-N pyrido[1,2-a]pyrimidin-4-one Chemical class C1=CC=CN2C(=O)C=CN=C21 NYJWYCAHJRGKMI-UHFFFAOYSA-N 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 abstract description 27
230000003389 potentiating effect Effects 0.000 abstract description 4
239000005557 antagonist Substances 0.000 abstract 1
239000000203 mixture Substances 0.000 description 47
239000000243 solution Substances 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
239000002585 base Substances 0.000 description 27
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
239000000543 intermediate Substances 0.000 description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
239000003480 eluent Substances 0.000 description 15
238000003756 stirring Methods 0.000 description 15
241000700159 Rattus Species 0.000 description 14
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 14
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
229960001701 chloroform Drugs 0.000 description 12
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
239000007858 starting material Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
150000003053 piperidines Chemical class 0.000 description 9
150000003930 2-aminopyridines Chemical class 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
238000009472 formulation Methods 0.000 description 7
230000003902 lesion Effects 0.000 description 7
229940076279 serotonin Drugs 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
239000003826 tablet Substances 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000002775 capsule Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
125000005843 halogen group Chemical group 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
235000017550 sodium carbonate Nutrition 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
229940001593 sodium carbonate Drugs 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000002202 Polyethylene glycol Substances 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
230000008602 contraction Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
239000008213 purified water Substances 0.000 description 5
210000002784 stomach Anatomy 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
229940082988 antihypertensives serotonin antagonists Drugs 0.000 description 4
239000003420 antiserotonin agent Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
229920002055 compound 48/80 Polymers 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
239000003937 drug carrier Substances 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
239000001267 polyvinylpyrrolidone Substances 0.000 description 4
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 4
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
239000012258 stirred mixture Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
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 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000007126 N-alkylation reaction Methods 0.000 description 3
229930040373 Paraformaldehyde Natural products 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000003513 alkali Substances 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
210000001367 artery Anatomy 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000001246 bromo group Chemical group Br* 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
239000000686 essence Substances 0.000 description 3
230000000762 glandular Effects 0.000 description 3
229960000443 hydrochloric acid Drugs 0.000 description 3
235000011167 hydrochloric acid Nutrition 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
235000014655 lactic acid Nutrition 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000007248 oxidative elimination reaction Methods 0.000 description 3
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230000000144 pharmacologic effect Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
230000035939 shock Effects 0.000 description 3
235000019333 sodium laurylsulphate Nutrition 0.000 description 3
239000008107 starch Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
BHWNQRHBJTYLBS-UHFFFAOYSA-N (3-methylphenyl)-(1-methylpiperidin-4-yl)methanone Chemical compound C1CN(C)CCC1C(=O)C1=CC=CC(C)=C1 BHWNQRHBJTYLBS-UHFFFAOYSA-N 0.000 description 2
VVKRQHYODGRELZ-UHFFFAOYSA-N 1-[4-(4-fluoro-2-hydroxybenzoyl)piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C(=O)C1=CC=C(F)C=C1O VVKRQHYODGRELZ-UHFFFAOYSA-N 0.000 description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 2
VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 2
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206010011703 Cyanosis Diseases 0.000 description 2
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NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
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235000011034 Rubus glaucus Nutrition 0.000 description 2
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125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
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125000004432 carbon atom Chemical group C* 0.000 description 2
150000001728 carbonyl compounds Chemical class 0.000 description 2
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239000000969 carrier Substances 0.000 description 2
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239000000938 histamine H1 antagonist Substances 0.000 description 2
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239000008172 hydrogenated vegetable oil Substances 0.000 description 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
125000002346 iodo group Chemical group I* 0.000 description 2
239000004310 lactic acid Substances 0.000 description 2
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IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000002227 vasoactive effect Effects 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000430092A 1980-03-28 1983-06-09 Derives de 3-(1-piperidinyalkyl)-4h-pyrido [1,2-a]-pyrimidin-4-one Expired CA1167843A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000430092A CA1167843A (fr)	1980-03-28	1983-06-09	Derives de 3-(1-piperidinyalkyl)-4h-pyrido [1,2-a]-pyrimidin-4-one

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US13484580A	1980-03-28	1980-03-28
US134,845		1980-03-28
US06/191,632 US4342870A (en)	1980-03-28	1980-09-29	Novel 3-(1-piperidinylalkyl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives
US191,632		1980-09-29
CA000372258A CA1163994A (fr)	1980-03-28	1981-03-04	Derives de la 3-(1-piperidinylalkyl)-4h-pyrido ¬1,2-a\|-pyrimidin-4-one
CA000430092A CA1167843A (fr)	1980-03-28	1983-06-09	Derives de 3-(1-piperidinyalkyl)-4h-pyrido [1,2-a]-pyrimidin-4-one

Publications (1)

Publication Number	Publication Date
CA1167843A true CA1167843A (fr)	1984-05-22

Family

ID=27426293

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000430092A Expired CA1167843A (fr)	1980-03-28	1983-06-09	Derives de 3-(1-piperidinyalkyl)-4h-pyrido [1,2-a]-pyrimidin-4-one

Country Status (1)

Country	Link
CA (1)	CA1167843A (fr)

1983
- 1983-06-09 CA CA000430092A patent/CA1167843A/fr not_active Expired

Publication	Publication Date	Title
US4342870A (en)	1982-08-03	Novel 3-(1-piperidinylalkyl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives
US4443451A (en)	1984-04-17	Bicyclic pyrimidin-5-one derivatives
US4335127A (en)	1982-06-15	Piperidinylalkyl quinazoline compounds, composition and method of use
US4485107A (en)	1984-11-27	[[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones
US5134147A (en)	1992-07-28	1,2-benzisoxazole compounds
EP0086422B1 (fr)	1987-09-30	Pyrazolo (4,3-c)pyridines à activité pharmacologique
US5292735A (en)	1994-03-08	Cyclic amide derivatives
US4581171A (en)	1986-04-08	[[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones useful for treating psychotropic disorders
EP0037713B1 (fr)	1984-02-08	Dérivés de 1,3-dihydro-1-((1-pipéridinyl)alkyl)-2H-benzimidazol-2-one
US4548938A (en)	1985-10-22	5-H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one compounds
KR850000413B1 (ko)	1985-03-26	3-(1-피페리디닐알킬)-4H-피리도[1, 2-a]피리미딘-4-온 유도체의 제조방법
AU593844B2 (en)	1990-02-22	N-substituted diphenylpiperidines
CA1246074A (fr)	1988-12-06	Derives de substitution hydroxyles ou amines de (piperidinylalcoyl)quinazolines
US4665075A (en)	1987-05-12	Derivatives of hydroxy- or amino-substituted (piperidinylalkyl)quinazolines
US4529727A (en)	1985-07-16	Pyrimido[2,1-b][1,3]-thiazines
CA1167843A (fr)	1984-05-22	Derives de 3-(1-piperidinyalkyl)-4h-pyrido [1,2-a]-pyrimidin-4-one
US4522945A (en)	1985-06-11	(Piperidinylalkyl) quinazoline derivatives
DE1695228C2 (de)	1984-02-16	5-Hydroxy-5-phenyl-2,3-dihydro-5H-imidazo-[2,1-a]isoindole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
US4533665A (en)	1985-08-06	[[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones
JPS5818390A (ja)	1983-02-02	二環式ピリミジン−５−オン誘導体、その製法および薬効成分としてのその用途

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Date	Code	Title	Description
2001-05-22	MKEX	Expiry