DD144056A5 - Verfahren zur herstellung von als histamin h tief 2-rezeptor-antagonisten wirkenden nitroverbindungen - Google Patents

Verfahren zur herstellung von als histamin h tief 2-rezeptor-antagonisten wirkenden nitroverbindungen Download PDF

Info

Publication number: DD144056A5
Authority: DD; German Democratic Republic
Prior art keywords: group; methyl; het; nitro; lower alkyl
Prior art date: 1978-05-30

Application number

DD79213269A

Other languages

German (de)

English (en)

Inventor

Michael L Roantree

Rodney C Young

Original Assignee

Smith Kline French Lab

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.)

1978-05-30

Filing date

1979-05-30

Publication date

1980-09-24

1979-05-30 Application filed by Smith Kline French Lab filed Critical Smith Kline French Lab

1980-09-24 Publication of DD144056A5 publication Critical patent/DD144056A5/de

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title claims description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 title description 54
229960001340 histamine Drugs 0.000 title description 27
239000002464 receptor antagonist Substances 0.000 title description 5
229940044551 receptor antagonist Drugs 0.000 title description 5
150000002828 nitro derivatives Chemical class 0.000 title description 2
-1 alkoxy radicals Chemical class 0.000 claims description 86
150000001875 compounds Chemical class 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 14
125000000623 heterocyclic group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Chemical group 0.000 claims description 5
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 claims description 2
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
150000005242 nitropyrroles Chemical class 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000005496 phosphonium group Chemical group 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical group C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims 3
PUVDYSURBUJQED-UHFFFAOYSA-N 3-methyl-4-nitro-1h-pyrrole Chemical compound CC1=CNC=C1[N+]([O-])=O PUVDYSURBUJQED-UHFFFAOYSA-N 0.000 claims 1
WERKCGAXQMDPFW-UHFFFAOYSA-N 3-nitro-4-phenyl-1h-pyrrole Chemical compound [O-][N+](=O)C1=CNC=C1C1=CC=CC=C1 WERKCGAXQMDPFW-UHFFFAOYSA-N 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
229920006395 saturated elastomer Polymers 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
150000003254 radicals Chemical class 0.000 description 22
239000000203 mixture Substances 0.000 description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 11
239000007787 solid Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
239000002904 solvent Substances 0.000 description 9
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
VNHRBDZDRWBDPB-UHFFFAOYSA-N 2-methylsulfinyl-3-nitro-1h-pyrrole Chemical compound CS(=O)C=1NC=CC=1[N+]([O-])=O VNHRBDZDRWBDPB-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
238000003756 stirring Methods 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
LOJNBPNACKZWAI-UHFFFAOYSA-N 3-nitro-1h-pyrrole Chemical compound [O-][N+](=O)C=1C=CNC=1 LOJNBPNACKZWAI-UHFFFAOYSA-N 0.000 description 5
229940125715 antihistaminic agent Drugs 0.000 description 5
239000000739 antihistaminic agent Substances 0.000 description 5
239000000825 pharmaceutical preparation Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
XTBZYMOXUSCADZ-UHFFFAOYSA-N 1-methylsulfanyl-1-methylsulfinyl-2-nitroethene Chemical group CSC(S(C)=O)=C[N+]([O-])=O XTBZYMOXUSCADZ-UHFFFAOYSA-N 0.000 description 4
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 4
229960000583 acetic acid Drugs 0.000 description 4
239000002585 base Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
230000027119 gastric acid secretion Effects 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 description 3
IQFWCHFUDDNBQG-UHFFFAOYSA-N 2-[[3-(ethylaminomethyl)-5-methylfuran-2-yl]methylsulfanyl]ethanamine Chemical compound CCNCC=1C=C(C)OC=1CSCCN IQFWCHFUDDNBQG-UHFFFAOYSA-N 0.000 description 3
YDLUFXQFKDNJBT-UHFFFAOYSA-N 2-methylsulfanyl-3-nitro-1h-pyrrole Chemical compound CSC=1NC=CC=1[N+]([O-])=O YDLUFXQFKDNJBT-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241000700159 Rattus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000010828 elution Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229960000582 mepyramine Drugs 0.000 description 3
YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
239000000047 product Substances 0.000 description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
RWCAZKKJQIFNJQ-UHFFFAOYSA-N 1-aminohexan-2-one;hydrochloride Chemical compound Cl.CCCCC(=O)CN RWCAZKKJQIFNJQ-UHFFFAOYSA-N 0.000 description 2
DZHRAAPBYAXYIC-UHFFFAOYSA-N 2-(2-aminoethylsulfanylmethyl)pyridin-3-amine Chemical compound NCCSCC1=NC=CC=C1N DZHRAAPBYAXYIC-UHFFFAOYSA-N 0.000 description 2
YTFSLUOQGOXGNB-UHFFFAOYSA-N 2-(2-aminoethylsulfanylmethyl)pyridin-3-ol Chemical compound NCCSCC1=NC=CC=C1O YTFSLUOQGOXGNB-UHFFFAOYSA-N 0.000 description 2
HMFFIMXUXASOJI-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=CC=CC=N1 HMFFIMXUXASOJI-UHFFFAOYSA-N 0.000 description 2
VGMZAKKUIGITCD-UHFFFAOYSA-N 2-[(3-methoxypyridin-2-yl)methylsulfanyl]ethanamine Chemical compound COC1=CC=CN=C1CSCCN VGMZAKKUIGITCD-UHFFFAOYSA-N 0.000 description 2
JFGCGQJHMUYGLU-UHFFFAOYSA-N 2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethanamine Chemical compound CN(C)CC1=CC=C(CSCCN)O1 JFGCGQJHMUYGLU-UHFFFAOYSA-N 0.000 description 2
GSVGBYAHGDCYDP-UHFFFAOYSA-N 2-methylsulfinyl-3-nitro-4-(2-phenylethyl)-1h-pyrrole Chemical compound [O-][N+](=O)C1=C(S(=O)C)NC=C1CCC1=CC=CC=C1 GSVGBYAHGDCYDP-UHFFFAOYSA-N 0.000 description 2
VXIBHLFYGRZKLL-UHFFFAOYSA-N 2-methylsulfinyl-3-nitro-4-phenyl-1h-pyrrole Chemical compound [O-][N+](=O)C1=C(S(=O)C)NC=C1C1=CC=CC=C1 VXIBHLFYGRZKLL-UHFFFAOYSA-N 0.000 description 2
IRTLROCMFSDSNF-UHFFFAOYSA-N 2-phenyl-1h-pyrrole Chemical compound C1=CNC(C=2C=CC=CC=2)=C1 IRTLROCMFSDSNF-UHFFFAOYSA-N 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
PNAQFQQNFKUJCT-UHFFFAOYSA-N 4-benzyl-2-methylsulfanyl-3-nitro-1h-pyrrole Chemical compound [O-][N+](=O)C1=C(SC)NC=C1CC1=CC=CC=C1 PNAQFQQNFKUJCT-UHFFFAOYSA-N 0.000 description 2
MPSOJYLNFNSPQQ-UHFFFAOYSA-N 4-butyl-2-methylsulfanyl-3-nitro-1h-pyrrole Chemical compound CCCCC1=CNC(SC)=C1[N+]([O-])=O MPSOJYLNFNSPQQ-UHFFFAOYSA-N 0.000 description 2
CQVIHCSWIJOZAM-UHFFFAOYSA-N 4-butyl-2-methylsulfinyl-3-nitro-1h-pyrrole Chemical compound CCCCC1=CNC(S(C)=O)=C1[N+]([O-])=O CQVIHCSWIJOZAM-UHFFFAOYSA-N 0.000 description 2
MDDKGTNAQJTDKU-UHFFFAOYSA-N 4-methyl-2-methylsulfanyl-3-nitro-1h-pyrrole Chemical compound CSC=1NC=C(C)C=1[N+]([O-])=O MDDKGTNAQJTDKU-UHFFFAOYSA-N 0.000 description 2
QZUFZEMNMNRKRW-UHFFFAOYSA-N 4-methyl-2-methylsulfinyl-3-nitro-1h-pyrrole Chemical compound CC1=CNC(S(C)=O)=C1[N+]([O-])=O QZUFZEMNMNRKRW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
IRJCRUXGZJIUCH-UHFFFAOYSA-N N-ethyl-3-nitro-1H-pyrrol-2-amine Chemical compound C(C)NC=1NC=CC=1[N+](=O)[O-] IRJCRUXGZJIUCH-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 1
MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 1
MSVQNSAIHJTFHR-UHFFFAOYSA-N 1-amino-3-phenylpropan-2-one;hydrochloride Chemical compound Cl.NCC(=O)CC1=CC=CC=C1 MSVQNSAIHJTFHR-UHFFFAOYSA-N 0.000 description 1
OHKDDAKDIQTBBJ-UHFFFAOYSA-N 1-amino-4-phenylbutan-2-one;hydrochloride Chemical compound Cl.NCC(=O)CCC1=CC=CC=C1 OHKDDAKDIQTBBJ-UHFFFAOYSA-N 0.000 description 1
GPFVECHZBIVMOS-UHFFFAOYSA-N 2,2-diethoxy-n-(1-methylsulfanyl-2-nitroethenyl)ethanamine Chemical group CCOC(OCC)CNC(SC)=C[N+]([O-])=O GPFVECHZBIVMOS-UHFFFAOYSA-N 0.000 description 1
SBBGPBUAEQEFNW-UHFFFAOYSA-N 2-(1,2,5-thiadiazol-3-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC=1C=NSN=1 SBBGPBUAEQEFNW-UHFFFAOYSA-N 0.000 description 1
GKIUPDRWOXMZDT-UHFFFAOYSA-N 2-(1,2-thiazol-3-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC=1C=CSN=1 GKIUPDRWOXMZDT-UHFFFAOYSA-N 0.000 description 1
CJIFBUZRANSSAI-UHFFFAOYSA-N 2-(1h-imidazol-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=NC=CN1 CJIFBUZRANSSAI-UHFFFAOYSA-N 0.000 description 1
CNMUGSJVSYLQOX-UHFFFAOYSA-N 2-(1h-imidazol-5-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=CNC=N1 CNMUGSJVSYLQOX-UHFFFAOYSA-N 0.000 description 1
KTPMWLYYQCYHKP-UHFFFAOYSA-N 2-[(3-chloropyridin-2-yl)methylsulfanyl]ethanamine;dihydrobromide Chemical compound Br.Br.NCCSCC1=NC=CC=C1Cl KTPMWLYYQCYHKP-UHFFFAOYSA-N 0.000 description 1
NTLFEXLXZRBDPP-UHFFFAOYSA-N 2-[(4-bromo-1h-imidazol-5-yl)methylsulfanyl]ethanamine Chemical compound NCCSCC=1NC=NC=1Br NTLFEXLXZRBDPP-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
ZUYBJAJYOKFDDQ-UHFFFAOYSA-N 2-methylsulfanyl-3-nitro-4-(2-phenylethyl)-1h-pyrrole Chemical compound [O-][N+](=O)C1=C(SC)NC=C1CCC1=CC=CC=C1 ZUYBJAJYOKFDDQ-UHFFFAOYSA-N 0.000 description 1
RUCLDQBBIJKQHO-UHFFFAOYSA-N 2-oxopropylazanium;chloride Chemical compound Cl.CC(=O)CN RUCLDQBBIJKQHO-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
YMECXFLZGYXWAR-UHFFFAOYSA-N 3-(2-phenylethyl)-1h-pyrrole Chemical compound C1=CNC=C1CCC1=CC=CC=C1 YMECXFLZGYXWAR-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
OGWNKQBYDIKVII-UHFFFAOYSA-N 3-nitro-n-[2-(pyridin-2-ylmethylsulfanyl)ethyl]-1h-pyrrol-2-amine Chemical compound C1=CNC(NCCSCC=2N=CC=CC=2)=C1[N+](=O)[O-] OGWNKQBYDIKVII-UHFFFAOYSA-N 0.000 description 1
NKHRYGIOQYSJRX-UHFFFAOYSA-N 3-nitro-n-[2-[[4-(trifluoromethyl)-1h-imidazol-5-yl]methylsulfanyl]ethyl]-1h-pyrrol-2-amine Chemical compound C1=CNC(NCCSCC2=C(NC=N2)C(F)(F)F)=C1[N+](=O)[O-] NKHRYGIOQYSJRX-UHFFFAOYSA-N 0.000 description 1
ZXBIXOCQHMQTFW-UHFFFAOYSA-N 4-benzyl-2-methylsulfinyl-3-nitro-1h-pyrrole Chemical compound [O-][N+](=O)C1=C(S(=O)C)NC=C1CC1=CC=CC=C1 ZXBIXOCQHMQTFW-UHFFFAOYSA-N 0.000 description 1
MLLYSQGRMFTIIZ-UHFFFAOYSA-N 5-(methylsulfanylmethyl)-1h-imidazole Chemical group CSCC1=CN=CN1 MLLYSQGRMFTIIZ-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
108010079943 Pentagastrin Proteins 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
229940124599 anti-inflammatory drug Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000000958 aryl methylene group Chemical group 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
238000009530 blood pressure measurement Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 1
229960003291 chlorphenamine Drugs 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
229960000520 diphenhydramine Drugs 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
230000037406 food intake Effects 0.000 description 1
235000012631 food intake Nutrition 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
238000010438 heat treatment Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PVRJOEAYRBQPLF-UHFFFAOYSA-N n-(2-hydroxypropyl)-n-(2-oxopropyl)nitrous amide Chemical compound CC(O)CN(N=O)CC(C)=O PVRJOEAYRBQPLF-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000002547 new drug Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
229960000444 pentagastrin Drugs 0.000 description 1
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/42—Nitro radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DD79213269A 1978-05-30 1979-05-30 Verfahren zur herstellung von als histamin h tief 2-rezeptor-antagonisten wirkenden nitroverbindungen DD144056A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB2411778		1978-05-30
GB7832313		1978-08-04

Publications (1)

Publication Number	Publication Date
DD144056A5 true DD144056A5 (de)	1980-09-24

Family

ID=26256929

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79213269A DD144056A5 (de)	1978-05-30	1979-05-30	Verfahren zur herstellung von als histamin h tief 2-rezeptor-antagonisten wirkenden nitroverbindungen

Country Status (19)

Country	Link
US (4)	US4238494A (fr)
EP (1)	EP0005985B1 (fr)
AR (1)	AR225285A1 (fr)
AU (1)	AU521405B2 (fr)
CA (1)	CA1124719A (fr)
DD (1)	DD144056A5 (fr)
DE (1)	DE2965270D1 (fr)
DK (1)	DK224079A (fr)
ES (1)	ES481119A1 (fr)
FI (1)	FI68399C (fr)
GR (1)	GR68026B (fr)
IE (1)	IE48756B1 (fr)
IL (1)	IL57415A (fr)
NO (1)	NO151008C (fr)
PH (1)	PH18500A (fr)
PL (1)	PL115380B1 (fr)
PT (1)	PT69687A (fr)
RO (1)	RO77448A (fr)
YU (1)	YU127279A (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL57415A (en) *	1978-05-30	1984-08-31	Smith Kline French Lab	Nitropyrrole compounds,process for preparing them and pharmaceutical compositions containing them
US4359466A (en) *	1979-10-24	1982-11-16	Smith Kline & French Laboratories Limited	Guanidine compounds
EP0089765A3 (fr) *	1982-03-17	1984-05-23	Smith Kline & French Laboratories Limited	Dérivés de pyridine
AU2222083A (en) *	1982-12-14	1984-06-21	Smith Kline & French Laboratories Limited	Pyridine derivatives
WO1984002907A1 (fr) *	1983-01-21	1984-08-02	Alkaloida Vegyeszeti Gyar	Nouveaux derives de diamines d'alcoyle
US4624958A (en) *	1983-04-14	1986-11-25	Pfizer Inc.	Antiprotozoal 1,4-di(p-amidinophenyl)imidazoles
JP3923079B2 (ja) *	1995-07-31	2007-05-30	塩野義製薬株式会社	ホスホリパーゼａ２阻害活性を有するピロリジン誘導体
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 (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3518251A (en) *	1967-06-07	1970-06-30	Geigy Ag J R	Certain aminoalkylamino substituted azacycloalkenes
GB1305550A (fr) *	1969-10-29	1973-02-07
US3734924A (en) *	1970-10-14	1973-05-22	Smith Kline French Lab	Carboxamidines
GB1400319A (en) *	1972-04-20	1975-07-16	Smith Kline French Lab	Pharmaceutical compositions
GB1419994A (en) *	1973-05-03	1976-01-07	Smith Kline French Lab	Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them
GB1421792A (en) *	1973-05-17	1976-01-21	Smith Kline French Lab	Heterocyclic substituted-1, 1-diamino-ethylene derivatives methods for their preparation and compositions containing them
GB1496787A (en) *	1974-03-12	1978-01-05	Smith Kline French Lab	Heteroalkylthioalkyl amidine derivatives
IL49528A (en) *	1975-05-21	1980-11-30	Smith Kline French Lab	Imidazolyl(or thiazolyl)methylthio(or butyl)guanidine or thiourea derivatives,their preparation and pharmaceutical compositions comprising them
GB1563090A (en) *	1975-07-31	1980-03-19	Smith Kline French Lab	Cyclobutene-diones
US4154834A (en) *	1975-12-29	1979-05-15	Smith Kline & French Laboratories Limited	Substituted isocytosines having histamine H2 -antagonist activity
GB1574214A (en) *	1976-03-11	1980-09-03	Smith Kline French Lab	Amidines
GB1565966A (en) *	1976-08-04	1980-04-23	Allen & Hanburys Ltd	Aminoalkyl furan derivatives
DE2645172C2 (de) *	1976-10-07	1982-02-18	Basf Ag, 6700 Ludwigshafen	Verfahren zur Herstellung von 4-Nitroimidazolen
DK168277A (da) *	1977-02-22	1978-08-23	Smithkline Corp	Fremgangsmaade til fremstilling af 4-substituerede imidazolforbindelser
IN151188B (fr) *	1978-02-13	1983-03-05	Smith Kline French Lab
IL57415A (en) *	1978-05-30	1984-08-31	Smith Kline French Lab	Nitropyrrole compounds,process for preparing them and pharmaceutical compositions containing them

1979
- 1979-05-28 IL IL57415A patent/IL57415A/xx unknown
- 1979-05-29 CA CA328,542A patent/CA1124719A/fr not_active Expired
- 1979-05-29 PT PT69687A patent/PT69687A/pt unknown
- 1979-05-29 EP EP79300973A patent/EP0005985B1/fr not_active Expired
- 1979-05-29 DE DE7979300973T patent/DE2965270D1/de not_active Expired
- 1979-05-29 PH PH22577A patent/PH18500A/en unknown
- 1979-05-29 NO NO791764A patent/NO151008C/no unknown
- 1979-05-30 FI FI791738A patent/FI68399C/fi not_active IP Right Cessation
- 1979-05-30 GR GR59218A patent/GR68026B/el unknown
- 1979-05-30 AR AR276723A patent/AR225285A1/es active
- 1979-05-30 DD DD79213269A patent/DD144056A5/de unknown
- 1979-05-30 RO RO7997681A patent/RO77448A/fr unknown
- 1979-05-30 PL PL1979215971A patent/PL115380B1/pl unknown
- 1979-05-30 AU AU47581/79A patent/AU521405B2/en not_active Ceased
- 1979-05-30 YU YU01272/79A patent/YU127279A/xx unknown
- 1979-05-30 ES ES481119A patent/ES481119A1/es not_active Expired
- 1979-05-30 DK DK224079A patent/DK224079A/da not_active Application Discontinuation
- 1979-05-30 US US06/043,786 patent/US4238494A/en not_active Expired - Lifetime
- 1979-08-08 IE IE1101/79A patent/IE48756B1/en unknown
1980
- 1980-06-16 US US06/159,524 patent/US4331668A/en not_active Expired - Lifetime
1982
- 1982-01-28 US US06/343,632 patent/US4407808A/en not_active Expired - Fee Related
1983
- 1983-06-27 US US06/507,814 patent/US4482563A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US4407808A (en)	1983-10-04
FI68399C (fi)	1985-09-10
IL57415A0 (en)	1979-09-30
NO151008C (no)	1985-01-23
AU4758179A (en)	1979-12-06
US4331668A (en)	1982-05-25
US4238494A (en)	1980-12-09
RO77448A (fr)	1981-11-04
YU127279A (en)	1983-04-30
IE48756B1 (en)	1985-05-15
US4482563A (en)	1984-11-13
EP0005985A1 (fr)	1979-12-12
FI791738A7 (fi)	1979-12-01
IE791101L (en)	1979-11-30
PH18500A (en)	1985-08-02
AR225285A1 (es)	1982-03-15
NO791764L (no)	1979-12-03
ES481119A1 (es)	1980-09-01
FI68399B (fi)	1985-05-31
DK224079A (da)	1979-12-01
IL57415A (en)	1984-08-31
GR68026B (fr)	1981-10-27
EP0005985B1 (fr)	1983-04-27
NO151008B (no)	1984-10-15
PT69687A (en)	1979-06-01
DE2965270D1 (en)	1983-06-01
PL115380B1 (en)	1981-03-31
CA1124719A (fr)	1982-06-01
AU521405B2 (en)	1982-04-01
PL215971A1 (fr)	1980-02-11

Publication	Publication Date	Title
DE3875073T2 (de)	1993-03-11	3-(4(1-substituierte-4-piperazinyl)butyl)-4-thiazolidinone, verfahren zu deren herstellung und ihre anwendung als arzneimittel.
CH624941A5 (fr)	1981-08-31
DD233374A5 (de)	1986-02-26	Verfahren zur herstellung von 2-(n-subst.-guanidino)-4-heteroarylthiazole
DE2846945A1 (de)	1979-05-03	Pharmazeutische praeparate
DE2528639A1 (de)	1976-01-15	Harnstoff-derivate, verfahren zu ihrer herstellung und arzneimittel
DD144057A5 (de)	1980-09-24	Verfahren zur herstellung von als histamin h tief 2-rezeptor-antagonisten wirkenden nitroverbindungen
DE2322880A1 (de)	1973-11-22	Neue organische verbindungen und verfahren zu deren herstellung
DE2651083A1 (de)	1978-05-18	Neue o-alkylierte hydroxylamine, verfahren zu ihrer herstellung und ihre verwendung
DD144056A5 (de)	1980-09-24	Verfahren zur herstellung von als histamin h tief 2-rezeptor-antagonisten wirkenden nitroverbindungen
CH630344A5 (en)	1982-06-15	Process for the preparation of novel O-(3-amino-2-hydroxypropyl)-amidoxime derivatives.
DE3442860A1 (de)	1986-05-28	5-alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3- on-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2604056A1 (de)	1976-08-05	Thiocarbaminsaeure-derivate
GB1565647A (en)	1980-04-23	Pharmacologically active compounds 4-substituted-imidazole-5-methanols
CH633288A5 (de)	1982-11-30	Verfahren zur herstellung von neuen heterocyclylaminoderivaten.
US4738969A (en)	1988-04-19	Substituted aminopyridones and aminoquinolones having histamine H2 -receptor blocking activity
EP0200947A1 (fr)	1986-11-12	Sels d'imidazolium substitué en position 1,3
DD223616A5 (de)	1985-06-19	Verfahren zur herstellung trisubstituierter oxazolidinone
AT390952B (de)	1990-07-25	Verfahren zur herstellung von neuen furan- oder thiophenderivaten
DE2514334A1 (de)	1975-10-09	Neue pyridinderivate, verfahren zu deren herstellung und ihre verwendung in pharmazeutischen zusammensetzungen
US4584384A (en)	1986-04-22	Nitro pyrroles
DE2811477A1 (de)	1978-09-21	1,2,4-triazin-5-on-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3685942T2 (de)	1992-12-24	2-pyridylessigsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zusammensetzungen.
EP0160173A1 (fr)	1985-11-06	Dérivés de benzothiazole, leurs procédés de préparation et médicament les contenant
DE1695910A1 (de)	1971-05-06	Verfahren zur Herstellung von neuen an der Aminogruppe substituierten 2-Amino-5-nitro-thiazolen
DE2707658A1 (de)	1977-09-01	Neue iminoverbindungen und verfahren zu ihrer herstellung