CY1561A - Pyrimidone derivatives - Google Patents

Pyrimidone derivatives Download PDF

Info

Publication number: CY1561A
Authority: CY; Cyprus
Prior art keywords: compound; formula; pyrimidone; acid addition; pharmaceutically acceptable
Prior art date: 1983-09-21

Application number

CY1561A

Other languages

English (en)

Original Assignee

Bristol Myers Squibb Co

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.)

1983-09-21

Filing date

1991-03-22

Publication date

1991-03-22

1991-03-22 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

1991-03-22 Publication of CY1561A publication Critical patent/CY1561A/en

Links

150000008318 pyrimidones Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 96
-1 carboalkoxy Chemical group 0.000 claims description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
231100000252 nontoxic Toxicity 0.000 claims description 19
230000003000 nontoxic effect Effects 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 15
238000010992 reflux Methods 0.000 claims description 15
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
239000012442 inert solvent Substances 0.000 claims description 12
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
239000007868 Raney catalyst Substances 0.000 claims description 4
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 4
229910000564 Raney nickel Inorganic materials 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
125000001589 carboacyl group Chemical group 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
230000009467 reduction Effects 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
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SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 3
229940077388 benzenesulfonate Drugs 0.000 claims description 3
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LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
230000003213 activating effect Effects 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
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125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
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150000002367 halogens Chemical class 0.000 claims description 2
125000001786 isothiazolyl group Chemical group 0.000 claims description 2
125000000842 isoxazolyl group Chemical group 0.000 claims description 2
125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
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239000003444 phase transfer catalyst Substances 0.000 claims description 2
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000005309 thioalkoxy group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims 1
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125000001309 chloro group Chemical group Cl* 0.000 claims 1
229940125810 compound 20 Drugs 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
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125000003373 pyrazinyl group Chemical group 0.000 claims 1
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230000011514 reflex Effects 0.000 claims 1
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CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 10
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WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 6
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 5
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
ZHQPCZZUXLSAAB-UHFFFAOYSA-N 2-methylsulfanyl-5-nitro-1h-pyrimidin-6-one Chemical compound CSC1=NC=C([N+]([O-])=O)C(O)=N1 ZHQPCZZUXLSAAB-UHFFFAOYSA-N 0.000 description 3
VQSXCZMVUMSITD-UHFFFAOYSA-N 3-[3-(piperidin-1-ylmethyl)phenoxy]propan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCCCC2)=C1 VQSXCZMVUMSITD-UHFFFAOYSA-N 0.000 description 3
PPOALEXDGIAFQH-UHFFFAOYSA-N 5-amino-2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]-1h-pyrimidin-6-one Chemical compound N1C(=O)C(N)=CN=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 PPOALEXDGIAFQH-UHFFFAOYSA-N 0.000 description 3
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RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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BWPREQYEXQAUOY-UHFFFAOYSA-N 5-nitro-2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]-1h-pyrimidin-6-one Chemical compound N1C(=O)C([N+](=O)[O-])=CN=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 BWPREQYEXQAUOY-UHFFFAOYSA-N 0.000 description 2
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RLOWMFIZVFMWBI-UHFFFAOYSA-N ethyl n-[6-oxo-2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino]-1h-pyrimidin-5-yl]carbamate Chemical compound N1C(=O)C(NC(=O)OCC)=CN=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 RLOWMFIZVFMWBI-UHFFFAOYSA-N 0.000 description 2
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AAEOEVRPMYKMKS-UHFFFAOYSA-N 3-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropan-1-amine Chemical compound C1=NC(OCCCN)=CC(CN2CCCCC2)=C1 AAEOEVRPMYKMKS-UHFFFAOYSA-N 0.000 description 1
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WEKYWIBCHONDBC-UHFFFAOYSA-N 3-[6-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCCCC2)=N1 WEKYWIBCHONDBC-UHFFFAOYSA-N 0.000 description 1
QCHHKUYJOJEKBO-UHFFFAOYSA-N 3-[6-[(dimethylamino)methyl]pyridin-2-yl]oxypropan-1-amine Chemical compound CN(C)CC1=CC=CC(OCCCN)=N1 QCHHKUYJOJEKBO-UHFFFAOYSA-N 0.000 description 1
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 1
NXZXEXYUXILDPU-UHFFFAOYSA-N 5-amino-2-[3-[3-(morpholin-4-ylmethyl)phenoxy]propylamino]-1h-pyrimidin-6-one Chemical compound N1C(=O)C(N)=CN=C1NCCCOC1=CC=CC(CN2CCOCC2)=C1 NXZXEXYUXILDPU-UHFFFAOYSA-N 0.000 description 1
ZQGXWORHWJBZFZ-UHFFFAOYSA-N 5-amino-2-[3-[3-[(dimethylamino)methyl]phenoxy]propylamino]-1h-pyrimidin-6-one Chemical compound CN(C)CC1=CC=CC(OCCCNC=2NC(=O)C(N)=CN=2)=C1 ZQGXWORHWJBZFZ-UHFFFAOYSA-N 0.000 description 1
UNLICQAETKKCLB-UHFFFAOYSA-N 5-amino-2-[3-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxypropylamino]-1h-pyrimidin-6-one Chemical compound N1C(=O)C(N)=CN=C1NCCCOC1=CC(CN2CCCCC2)=CC=N1 UNLICQAETKKCLB-UHFFFAOYSA-N 0.000 description 1
PBWONTNRDDSJFX-UHFFFAOYSA-N 5-amino-2-[3-[4-[(dimethylamino)methyl]pyridin-2-yl]oxypropylamino]-1h-pyrimidin-6-one Chemical compound CN(C)CC1=CC=NC(OCCCNC=2NC(=O)C(N)=CN=2)=C1 PBWONTNRDDSJFX-UHFFFAOYSA-N 0.000 description 1
LNTSEUKLRDTZHQ-UHFFFAOYSA-N 5-amino-2-[3-[6-[(dimethylamino)methyl]pyridin-2-yl]oxypropylamino]-1h-pyrimidin-6-one Chemical compound CN(C)CC1=CC=CC(OCCCNC=2NC(=O)C(N)=CN=2)=N1 LNTSEUKLRDTZHQ-UHFFFAOYSA-N 0.000 description 1
DBAKFASWICGISY-BTJKTKAUSA-N Chlorpheniramine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 DBAKFASWICGISY-BTJKTKAUSA-N 0.000 description 1
229920004943 Delrin® Polymers 0.000 description 1
206010016717 Fistula Diseases 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
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229910017974 NH40H Inorganic materials 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
241001433070 Xiphoides Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000003699 antiulcer agent Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229940046978 chlorpheniramine maleate Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000013068 control sample Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000013461 design Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000011833 dog model Methods 0.000 description 1
230000000857 drug effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000003890 fistula Effects 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
238000003304 gavage Methods 0.000 description 1
230000036541 health Effects 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
238000013289 male long evans rat Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 1
229960002455 methoxyflurane Drugs 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000001711 oxyntic cell Anatomy 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
208000011906 peptic ulcer disease Diseases 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
239000000843 powder Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
239000006215 rectal suppository Substances 0.000 description 1
229940100618 rectal suppository Drugs 0.000 description 1
238000011160 research Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
210000003752 saphenous vein Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000004448 titration Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
210000001113 umbilicus Anatomy 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
210000002417 xiphoid bone Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

CY1561A 1983-09-21 1991-03-22 Pyrimidone derivatives CY1561A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/534,426 US4772704A (en)	1983-09-21	1983-09-21	2,5-disubstituted-4(3H)-pyrimidones having histamine H2 -receptor antagonist activity

Publications (1)

Publication Number	Publication Date
CY1561A true CY1561A (en)	1991-03-22

Family

ID=24129972

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CY1561A CY1561A (en)	1983-09-21	1991-03-22	Pyrimidone derivatives

Country Status (36)

Country	Link
US (1)	US4772704A (ko)
JP (1)	JPH0643310B2 (ko)
KR (1)	KR900001198B1 (ko)
AR (2)	AR242385A1 (ko)
AT (1)	AT387965B (ko)
AU (1)	AU583479B2 (ko)
BE (1)	BE900652A (ko)
CA (1)	CA1260463A (ko)
CH (1)	CH665840A5 (ko)
CS (1)	CS249147B2 (ko)
CY (1)	CY1561A (ko)
DD (1)	DD226881A5 (ko)
DE (1)	DE3434578A1 (ko)
DK (1)	DK162987C (ko)
ES (4)	ES8607253A1 (ko)
FI (1)	FI83868C (ko)
FR (1)	FR2552082B1 (ko)
GB (1)	GB2146994B (ko)
GR (1)	GR80439B (ko)
HK (1)	HK73790A (ko)
HU (1)	HU193227B (ko)
IE (1)	IE58083B1 (ko)
IL (1)	IL72990A (ko)
IT (1)	IT1176739B (ko)
LU (1)	LU85550A1 (ko)
NL (1)	NL8402898A (ko)
NO (1)	NO161561C (ko)
NZ (1)	NZ209572A (ko)
OA (1)	OA07820A (ko)
PT (1)	PT79256B (ko)
SE (1)	SE463209B (ko)
SG (1)	SG60890G (ko)
YU (1)	YU45205B (ko)
ZA (1)	ZA847345B (ko)
ZM (1)	ZM4984A1 (ko)
ZW (1)	ZW16084A1 (ko)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2873340B2 (ja) *	1988-04-29	1999-03-24	武田薬品工業株式会社	抗生物質ｔａｎ―１０５７，その製造法および用途
US20230349922A1 (en)	2020-08-11	2023-11-02	Université De Strasbourg	H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IN151188B (ko) *	1978-02-13	1983-03-05	Smith Kline French Lab
ES477520A1 (es) *	1978-02-25	1979-06-01	Thomae Gmbh Dr K	Procedimiento para la preparacion de nuevas penicilinas.
PH16240A (en) *	1978-04-11	1983-08-11	Smith Kline French Lab	Process for making histamine antagonist
US4496567A (en) *	1978-11-13	1985-01-29	Smith Kline & French Laboratories Limited	Phenyl alkylaminopyrimidones
US4521418A (en) *	1979-02-21	1985-06-04	Smith Kline & French Laboratories Limited	Guanidinothiazolyl derivatives
AU531142B2 (en) *	1979-04-04	1983-08-11	Smith Kline & French Laboratories Limited	2 amino- pyimindones
CA1140129A (en) *	1979-08-21	1983-01-25	Ronald J. King	4-pyrimidone derivatives
ZW21281A1 (en) *	1980-10-01	1981-11-18	Smith Kline French Lab	Amine derivatives
US4352933A (en) *	1981-02-06	1982-10-05	Smithkline Beckman Corporation	Chemical methods and intermediates for preparing substituted pyrimidinones
NZ202797A (en) *	1981-12-28	1985-08-30	Lilly Co Eli	Pyrimidine derivatives and pharmaceutical compositions
US4468399A (en) *	1981-12-28	1984-08-28	Eli Lilly And Company	2-[2-(2-Aminoalkyl-4-thiazolylmethylthio)alkyl]-amino-5-substituted-4-pyrimidones
GB8320505D0 (en) *	1983-07-29	1983-09-01	Smith Kline French Lab	Chemical compounds
CA1275097A (en) *	1984-10-02	1990-10-09	Fujio Nohara	Pyridyloxy derivatives

1983
- 1983-09-21 US US06/534,426 patent/US4772704A/en not_active Expired - Fee Related
1984
- 1984-09-17 NZ NZ209572A patent/NZ209572A/en unknown
- 1984-09-18 IL IL72990A patent/IL72990A/xx not_active IP Right Cessation
- 1984-09-18 ZA ZA847345A patent/ZA847345B/xx unknown
- 1984-09-18 FI FI843643A patent/FI83868C/fi not_active IP Right Cessation
- 1984-09-18 ZM ZM49/84A patent/ZM4984A1/xx unknown
- 1984-09-18 ZW ZW160/84A patent/ZW16084A1/xx unknown
- 1984-09-19 NO NO843726A patent/NO161561C/no unknown
- 1984-09-19 ES ES536054A patent/ES8607253A1/es not_active Expired
- 1984-09-19 CA CA000463533A patent/CA1260463A/en not_active Expired
- 1984-09-19 YU YU1613/84A patent/YU45205B/xx unknown
- 1984-09-20 HU HU843539A patent/HU193227B/hu not_active IP Right Cessation
- 1984-09-20 DK DK450484A patent/DK162987C/da active
- 1984-09-20 OA OA58396A patent/OA07820A/xx unknown
- 1984-09-20 DE DE19843434578 patent/DE3434578A1/de not_active Withdrawn
- 1984-09-20 CH CH4510/84A patent/CH665840A5/de not_active IP Right Cessation
- 1984-09-20 JP JP59195868A patent/JPH0643310B2/ja not_active Expired - Lifetime
- 1984-09-20 CS CS847103A patent/CS249147B2/cs unknown
- 1984-09-20 IT IT22744/84A patent/IT1176739B/it active
- 1984-09-20 SE SE8404729A patent/SE463209B/sv not_active IP Right Cessation
- 1984-09-20 GB GB08423863A patent/GB2146994B/en not_active Expired
- 1984-09-20 FR FR8414463A patent/FR2552082B1/fr not_active Expired
- 1984-09-20 AU AU33351/84A patent/AU583479B2/en not_active Ceased
- 1984-09-20 IE IE240684A patent/IE58083B1/en not_active IP Right Cessation
- 1984-09-21 PT PT79256A patent/PT79256B/pt not_active IP Right Cessation
- 1984-09-21 KR KR1019840005791A patent/KR900001198B1/ko not_active Expired
- 1984-09-21 GR GR80439A patent/GR80439B/el unknown
- 1984-09-21 NL NL8402898A patent/NL8402898A/nl not_active Application Discontinuation
- 1984-09-21 AT AT0300984A patent/AT387965B/de not_active IP Right Cessation
- 1984-09-21 BE BE0/213705A patent/BE900652A/fr not_active IP Right Cessation
- 1984-09-21 LU LU85550A patent/LU85550A1/fr unknown
- 1984-09-21 DD DD84267496A patent/DD226881A5/de not_active IP Right Cessation
- 1984-09-21 AR AR84298041A patent/AR242385A1/es active
1985
- 1985-06-14 ES ES544213A patent/ES8704465A1/es not_active Expired
1986
- 1986-01-31 ES ES551501A patent/ES8702897A1/es not_active Expired
- 1986-01-31 ES ES551500A patent/ES8704155A1/es not_active Expired
1987
- 1987-09-18 AR AR87308766A patent/AR242789A1/es active
1990
- 1990-07-21 SG SG608/90A patent/SG60890G/en unknown
- 1990-09-20 HK HK737/90A patent/HK73790A/xx unknown
1991
- 1991-03-22 CY CY1561A patent/CY1561A/en unknown

Also Published As

Publication number	Publication date
GB8423863D0 (en)	1984-10-24
FI83868C (fi)	1991-09-10
ES544213A0 (es)	1987-04-01
NO843726L (no)	1985-03-22
YU45205B (en)	1992-05-28
BE900652A (fr)	1985-03-21
ZW16084A1 (en)	1985-01-16
GR80439B (en)	1985-01-22
NL8402898A (nl)	1985-04-16
ES551501A0 (es)	1987-01-16
NO161561C (no)	1989-08-30
SE8404729L (sv)	1985-03-22
DK162987B (da)	1992-01-06
IT1176739B (it)	1987-08-18
IT8422744A1 (it)	1986-03-20
AU3335184A (en)	1985-03-28
NO161561B (no)	1989-05-22
DE3434578A1 (de)	1985-04-11
FI83868B (fi)	1991-05-31
AT387965B (de)	1989-04-10
CH665840A5 (de)	1988-06-15
AR242789A1 (es)	1993-05-31
IE58083B1 (en)	1993-06-30
DK162987C (da)	1992-06-01
KR900001198B1 (ko)	1990-02-28
YU161384A (en)	1987-12-31
FR2552082B1 (fr)	1987-02-20
HK73790A (en)	1990-09-28
DK450484D0 (da)	1984-09-20
ES551500A0 (es)	1987-03-16
GB2146994B (en)	1987-09-03
FR2552082A1 (fr)	1985-03-22
ES8704465A1 (es)	1987-04-01
IT8422744A0 (it)	1984-09-20
ES8704155A1 (es)	1987-03-16
GB2146994A (en)	1985-05-01
SG60890G (en)	1990-09-07
LU85550A1 (fr)	1985-06-04
JPS6087271A (ja)	1985-05-16
NZ209572A (en)	1988-05-30
FI843643L (fi)	1985-03-22
IE842406L (en)	1985-03-21
IL72990A (en)	1990-07-12
JPH0643310B2 (ja)	1994-06-08
ZM4984A1 (en)	1985-05-21
HUT35259A (en)	1985-06-28
AU583479B2 (en)	1989-05-04
KR850002259A (ko)	1985-05-10
DK450484A (da)	1985-03-22
ATA300984A (de)	1988-09-15
CA1260463A (en)	1989-09-26
PT79256A (en)	1984-10-01
FI843643A0 (fi)	1984-09-18
AR242385A1 (es)	1993-03-31
ES8607253A1 (es)	1986-05-16
ZA847345B (en)	1985-06-26
CS249147B2 (en)	1987-03-12
PT79256B (en)	1986-11-20
SE8404729D0 (sv)	1984-09-20
HU193227B (en)	1987-08-28
SE463209B (sv)	1990-10-22
OA07820A (fr)	1986-11-20
US4772704A (en)	1988-09-20
DD226881A5 (de)	1985-09-04
ES536054A0 (es)	1986-05-16
ES8702897A1 (es)	1987-01-16

Publication	Publication Date	Title
US4390701A (en)	1983-06-28	1-Amino-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dione
US4128658A (en)	1978-12-05	Aminoalkyl furan derivatives
SU1400508A3 (ru)	1988-05-30	Способ получени производных арилтиазолов
US4522943A (en)	1985-06-11	Chemical compounds
JPS62252780A (ja)	1987-11-04	新規なインデノチアゾ−ル誘導体及びその製造法
US4526973A (en)	1985-07-02	Chemical compounds
US4395553A (en)	1983-07-26	Chemical compounds
JPH05262761A (ja)	1993-10-12	アリールアルキルアミン誘導体
US4503051A (en)	1985-03-05	Substituted 3-cyclobutene-1,2-diones, pharmaceutical compositions thereof and methods of use
CY1561A (en)	1991-03-22	Pyrimidone derivatives
US4539316A (en)	1985-09-03	Pyridine derivatives of 1,2-diaminocyclobutene-3,4-diones
US4169855A (en)	1979-10-02	N'-derivatives of n-(2-mercapto-ethyl)-2-nitro-1,1-ethenediamine
US4507485A (en)	1985-03-26	3,4-Disubstituted-1,2,5-oxadiazoles having histamine H2 -receptor antagonist activity
US4546188A (en)	1985-10-08	Substituted 1,2-diaminocyclobutene-3,4-diones
US4607105A (en)	1986-08-19	3-cyclobutene-1,2-dione intermediates
US4788184A (en)	1988-11-29	Substituted 3-cyclobutene-1,2-diones as anti-ulcer agents
IE47543B1 (en)	1984-04-18	Guanidine derivatives
GB2147899A (en)	1985-05-22	Chemical intermediates derived from cyclobutene
EP0091220A2 (en)	1983-10-12	Thiazole derivatives, process for their preparation and pharmaceutical compositions containing them
JPS61115074A (ja)	1986-06-02	３，４‐ジアゾール誘導体、その製法、およびその化合物を含有する医薬品
KR810000355B1 (ko)	1981-04-22	아미노 알킬푸란 유도체의 제조방법
US3935268A (en)	1976-01-27	ω-[Bis(ω,ω-diphenylalkyl)amino]alkan-ol and their salts
DK149812B (da)	1986-10-06	Analogifremgangsmaade til fremstilling af aminoalkylfuranderivater