LU85550A1 - 2,5-disubstituees-4(3h)-pyrimidones ayant une activite antagoniste receptrice histamine h2,et compositions pharmaceutiques contenant de tels composes a titre d'ingredients actifs - Google Patents

2,5-disubstituees-4(3h)-pyrimidones ayant une activite antagoniste receptrice histamine h2,et compositions pharmaceutiques contenant de tels composes a titre d'ingredients actifs Download PDF

Info

Publication number: LU85550A1
Authority: LU; Luxembourg
Prior art keywords: compound; formula; pyrimidone; alkyl; pharmaceutically acceptable
Prior art date: 1983-09-21

Application number

LU85550A

Other languages

English (en)

French (fr)

Original Assignee

Bristol Myers 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

1984-09-21

Publication date

1985-06-04

1984-09-21 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1985-06-04 Publication of LU85550A1 publication Critical patent/LU85550A1/fr

Links

150000001875 compounds Chemical class 0.000 title claims description 93
239000004480 active ingredient Substances 0.000 title claims description 5
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
239000003485 histamine H2 receptor antagonist Substances 0.000 title description 7
230000000694 effects Effects 0.000 title description 6
229940122957 Histamine H2 receptor antagonist Drugs 0.000 title description 4
-1 carboalkoxy Chemical group 0.000 claims description 91
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 29
238000006243 chemical reaction Methods 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 26
231100000252 nontoxic Toxicity 0.000 claims description 20
230000003000 nontoxic effect Effects 0.000 claims description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 16
238000010992 reflux Methods 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
239000012442 inert solvent Substances 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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
125000005843 halogen group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
239000007868 Raney catalyst Substances 0.000 claims description 3
229910000564 Raney nickel Inorganic materials 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 2
230000003213 activating effect Effects 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 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
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000002346 iodo group Chemical group I* 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
238000004519 manufacturing process Methods 0.000 claims description 2
125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
239000003444 phase transfer catalyst Substances 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
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
125000001425 triazolyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
238000007792 addition Methods 0.000 claims 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 claims 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
125000005309 thioalkoxy group Chemical group 0.000 claims 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 15
230000002496 gastric effect Effects 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
241000282472 Canis lupus familiaris Species 0.000 description 11
241001465754 Metazoa Species 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
229960001380 cimetidine Drugs 0.000 description 10
CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
238000003818 flash chromatography Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 9
239000000523 sample Substances 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000003814 drug Substances 0.000 description 8
238000010828 elution Methods 0.000 description 8
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 8
230000028327 secretion Effects 0.000 description 8
238000012360 testing method Methods 0.000 description 8
229940079593 drug Drugs 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
241000700159 Rattus Species 0.000 description 5
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
210000002784 stomach Anatomy 0.000 description 5
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 4
230000003197 catalytic effect Effects 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
FPBPLBWLMYGIQR-UHFFFAOYSA-N Metiamide Chemical compound CNC(=S)NCCSCC=1N=CNC=1C FPBPLBWLMYGIQR-UHFFFAOYSA-N 0.000 description 3
208000008469 Peptic Ulcer Diseases 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
229960001340 histamine Drugs 0.000 description 3
238000001802 infusion Methods 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
229950003251 metiamide Drugs 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
239000004033 plastic Substances 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
150000008081 1H-pyrimidin-4-ones Chemical class 0.000 description 2
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
201000010000 Agranulocytosis Diseases 0.000 description 2
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-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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VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
238000004448 titration Methods 0.000 description 2
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GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
AGYXIUAGBLMBGV-UHFFFAOYSA-N 3,5-dimethylpyrazole-1-carboximidamide;nitric acid Chemical compound O[N+]([O-])=O.CC=1C=C(C)N(C(N)=N)N=1 AGYXIUAGBLMBGV-UHFFFAOYSA-N 0.000 description 1
DXFZTDREQLPNEI-UHFFFAOYSA-N 3-[3-(azepan-1-ylmethyl)phenoxy]propan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCCCCC2)=C1 DXFZTDREQLPNEI-UHFFFAOYSA-N 0.000 description 1
BPUOHUMZZKDGLM-UHFFFAOYSA-N 3-[3-(morpholin-4-ylmethyl)phenoxy]propan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCOCC2)=C1 BPUOHUMZZKDGLM-UHFFFAOYSA-N 0.000 description 1
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CETVCWCSADQUBA-UHFFFAOYSA-N 3-[3-(piperidin-1-ylmethyl)phenyl]sulfanylpropan-1-amine Chemical compound NCCCSC1=CC=CC(CN2CCCCC2)=C1 CETVCWCSADQUBA-UHFFFAOYSA-N 0.000 description 1
QXKZJYVGGKDGHX-UHFFFAOYSA-N 3-[3-(pyrrolidin-1-ylmethyl)phenoxy]propan-1-amine Chemical compound NCCCOC1=CC=CC(CN2CCCC2)=C1 QXKZJYVGGKDGHX-UHFFFAOYSA-N 0.000 description 1
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210000002421 cell wall Anatomy 0.000 description 1
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239000013068 control sample Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
239000003937 drug carrier Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
DSJGGCNLTRBACZ-UHFFFAOYSA-N ethyl 2-(ethoxycarbonylamino)-3-oxopropanoate Chemical compound CCOC(=O)NC(C=O)C(=O)OCC DSJGGCNLTRBACZ-UHFFFAOYSA-N 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
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
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
238000013289 male long evans rat Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 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
BMCCPABJCHMZNM-UHFFFAOYSA-N nitric acid;2-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]guanidine Chemical compound O[N+]([O-])=O.NC(N)=NCCCOC1=CC=CC(CN2CCCCC2)=C1 BMCCPABJCHMZNM-UHFFFAOYSA-N 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
150000008318 pyrimidones Chemical class 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
238000005070 sampling Methods 0.000 description 1
210000003752 saphenous vein Anatomy 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
239000012265 solid product Substances 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
238000010998 test method Methods 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
AWLILQARPMWUHA-UHFFFAOYSA-M thiopental sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC([S-])=NC1=O AWLILQARPMWUHA-UHFFFAOYSA-M 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
210000001113 umbilicus Anatomy 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)

LU85550A 1983-09-21 1984-09-21 2,5-disubstituees-4(3h)-pyrimidones ayant une activite antagoniste receptrice histamine h2,et compositions pharmaceutiques contenant de tels composes a titre d'ingredients actifs LU85550A1 (fr)

Applications Claiming Priority (2)

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
US53442683		1983-09-21

Publications (1)

Publication Number	Publication Date
LU85550A1 true LU85550A1 (fr)	1985-06-04

Family

ID=24129972

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU85550A LU85550A1 (fr)	1983-09-21	1984-09-21	2,5-disubstituees-4(3h)-pyrimidones ayant une activite antagoniste receptrice histamine h2,et compositions pharmaceutiques contenant de tels composes a titre d'ingredients actifs

Country Status (36)

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

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
WO2022034121A1 (en)	2020-08-11	2022-02-17	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 (de) *	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 ZW ZW160/84A patent/ZW16084A1/xx unknown
- 1984-09-18 IL IL72990A patent/IL72990A/xx not_active IP Right Cessation
- 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 ZA ZA847345A patent/ZA847345B/xx unknown
- 1984-09-19 ES ES536054A patent/ES8607253A1/es not_active Expired
- 1984-09-19 NO NO843726A patent/NO161561C/no unknown
- 1984-09-19 CA CA000463533A patent/CA1260463A/en not_active Expired
- 1984-09-19 YU YU1613/84A patent/YU45205B/xx unknown
- 1984-09-20 IT IT22744/84A patent/IT1176739B/it active
- 1984-09-20 DK DK450484A patent/DK162987C/da active
- 1984-09-20 DE DE19843434578 patent/DE3434578A1/de not_active Withdrawn
- 1984-09-20 OA OA58396A patent/OA07820A/xx unknown
- 1984-09-20 CS CS847103A patent/CS249147B2/cs unknown
- 1984-09-20 FR FR8414463A patent/FR2552082B1/fr not_active Expired
- 1984-09-20 IE IE240684A patent/IE58083B1/en not_active IP Right Cessation
- 1984-09-20 AU AU33351/84A patent/AU583479B2/en not_active Ceased
- 1984-09-20 JP JP59195868A patent/JPH0643310B2/ja not_active Expired - Lifetime
- 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 HU HU843539A patent/HU193227B/hu not_active IP Right Cessation
- 1984-09-20 CH CH4510/84A patent/CH665840A5/de not_active IP Right Cessation
- 1984-09-21 DD DD84267496A patent/DD226881A5/de not_active IP Right Cessation
- 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 PT PT79256A patent/PT79256B/pt not_active IP Right Cessation
- 1984-09-21 GR GR80439A patent/GR80439B/el unknown
- 1984-09-21 LU LU85550A patent/LU85550A1/fr unknown
- 1984-09-21 KR KR1019840005791A patent/KR900001198B1/ko not_active Expired
- 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 ES551500A patent/ES8704155A1/es not_active Expired
- 1986-01-31 ES ES551501A patent/ES8702897A1/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
IT8422744A1 (it)	1986-03-20
DK450484D0 (da)	1984-09-20
SE8404729L (sv)	1985-03-22
FR2552082A1 (fr)	1985-03-22
DK162987B (da)	1992-01-06
IL72990A (en)	1990-07-12
HUT35259A (en)	1985-06-28
CA1260463A (en)	1989-09-26
HU193227B (en)	1987-08-28
FR2552082B1 (fr)	1987-02-20
KR850002259A (ko)	1985-05-10
ES8702897A1 (es)	1987-01-16
GB2146994A (en)	1985-05-01
SG60890G (en)	1990-09-07
ES544213A0 (es)	1987-04-01
AT387965B (de)	1989-04-10
IE842406L (en)	1985-03-21
AR242789A1 (es)	1993-05-31
YU45205B (en)	1992-05-28
AU3335184A (en)	1985-03-28
CS249147B2 (en)	1987-03-12
ES8704465A1 (es)	1987-04-01
IT8422744A0 (it)	1984-09-20
ES8607253A1 (es)	1986-05-16
IT1176739B (it)	1987-08-18
HK73790A (en)	1990-09-28
NL8402898A (nl)	1985-04-16
YU161384A (en)	1987-12-31
DD226881A5 (de)	1985-09-04
DK162987C (da)	1992-06-01
JPH0643310B2 (ja)	1994-06-08
KR900001198B1 (ko)	1990-02-28
US4772704A (en)	1988-09-20
ZA847345B (en)	1985-06-26
NO161561B (no)	1989-05-22
NZ209572A (en)	1988-05-30
CH665840A5 (de)	1988-06-15
FI83868B (fi)	1991-05-31
BE900652A (fr)	1985-03-21
PT79256B (en)	1986-11-20
IE58083B1 (en)	1993-06-30
FI843643L (fi)	1985-03-22
ZM4984A1 (en)	1985-05-21
SE8404729D0 (sv)	1984-09-20
PT79256A (en)	1984-10-01
FI843643A0 (fi)	1984-09-18
GR80439B (en)	1985-01-22
ES551500A0 (es)	1987-03-16
ATA300984A (de)	1988-09-15
ES536054A0 (es)	1986-05-16
CY1561A (en)	1991-03-22
ZW16084A1 (en)	1985-01-16
ES551501A0 (es)	1987-01-16
AR242385A1 (es)	1993-03-31
SE463209B (sv)	1990-10-22
OA07820A (fr)	1986-11-20
GB8423863D0 (en)	1984-10-24
JPS6087271A (ja)	1985-05-16
DE3434578A1 (de)	1985-04-11
NO843726L (no)	1985-03-22
NO161561C (no)	1989-08-30
AU583479B2 (en)	1989-05-04
GB2146994B (en)	1987-09-03
FI83868C (fi)	1991-09-10
ES8704155A1 (es)	1987-03-16
DK450484A (da)	1985-03-22

Publication	Publication Date	Title
FR2505835A1 (fr)	1982-11-19	Nouvelles 1,2-diaminocyclobutene-3,4-diones, leur procede de preparation et composition pharmaceutique les contenant
FR2823209A1 (fr)	2002-10-11	Nouvelles thiohydantoines et leur utilisation en therapeutique
CH639653A5 (fr)	1983-11-30	Aminothiazoles et composition pharmaceutique les contenant.
CA2150162C (fr)	2002-05-14	Nouveau n-pyridyl carboxamides et derives, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
WO2013177241A1 (en)	2013-11-28	Method for synthesizing cycloalkanyl(b}indoles, cycloalkanyl(b) benzofurans, cycloalkanyl(b)benzothiophenes, compounds and methods of use
IL41825A (en)	1977-03-31	Pyridine derivatives their preparation and pharmaceutical compositions containing them
BE898278A (fr)	1984-05-22	Benzoxazines antipsychotiques.
FR2489823A1 (fr)	1982-03-12	Nouvelles n-((4-(3-pyridyle substitue en position 3)-piperazino)alkyl)azaspirodecanediones, leur procede de preparation et medicament les contenant
DK158460B (da)	1990-05-21	Analogifremgangsmaade til fremstilling af substituerede oxocarboxylsyrer
KR100372312B1 (ko)	2003-05-09	신규의히드록시믹산유도체,그를포함한약제학적조성물및그의제조방법
WO1989002890A1 (fr)	1989-04-06	Composes de thiohydantoine
FR2581064A1 (fr)	1986-10-31	Derive antipsychotique a base de 8-(4-(4-(1-exo-1,2-benzisothiazol-3-yl)-1-piperazinyl)-butyl)-8-azaspiro(4,5)decane-7,9-dione et son procede de preparation
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