HU180082B - Eljárás nitropirrol-származékok előállítására - Google Patents

Eljárás nitropirrol-származékok előállítására Download PDF

Info

Publication number: HU180082B
Authority: HU; Hungary
Prior art keywords: nitro; methyl; imidazolylmethylthio; ethylamine; preparation
Prior art date: 1978-05-30

Application number

Other languages

English (en)

Hungarian (hu)

Inventor

Michael L Roanree

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

1979-05-29

Publication date

1983-01-28

1979-05-29 Application filed by Smith Kline French Lab filed Critical Smith Kline French Lab

1983-01-28 Publication of HU180082B publication Critical patent/HU180082B/hu

Links

238000000034 method Methods 0.000 title claims description 11
150000005242 nitropyrroles Chemical class 0.000 title description 3
-1 5-methylimidazolyl Chemical group 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 9
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 claims description 7
JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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 claims description 3
IKMJAJBEVMAMBH-UHFFFAOYSA-N 4-methyl-n-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-3-nitro-1h-pyrrol-2-amine Chemical compound CC1=CNC(NCCSCC2=C(NC=N2)C)=C1[N+]([O-])=O IKMJAJBEVMAMBH-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
CBPMJSWKGZBBSW-UHFFFAOYSA-N CS(=O)(=O)C=1NC=C(C1[N+](=O)[O-])C Chemical compound CS(=O)(=O)C=1NC=C(C1[N+](=O)[O-])C CBPMJSWKGZBBSW-UHFFFAOYSA-N 0.000 claims 1
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims 1
PNZDZRMOBIIQTC-UHFFFAOYSA-N ethanamine;hydron;bromide Chemical compound Br.CCN PNZDZRMOBIIQTC-UHFFFAOYSA-N 0.000 claims 1
150000002828 nitro derivatives Chemical class 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 18
229960001340 histamine Drugs 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
238000004458 analytical method Methods 0.000 description 12
239000007787 solid Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
102000005962 receptors Human genes 0.000 description 9
108020003175 receptors Proteins 0.000 description 9
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
229940093499 ethyl acetate Drugs 0.000 description 8
239000002904 solvent Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
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 5
YDLUFXQFKDNJBT-UHFFFAOYSA-N 2-methylsulfanyl-3-nitro-1h-pyrrole Chemical compound CSC=1NC=CC=1[N+]([O-])=O YDLUFXQFKDNJBT-UHFFFAOYSA-N 0.000 description 5
230000004071 biological effect Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
239000000739 antihistaminic agent Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
238000010828 elution Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
230000001404 mediated effect Effects 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229940122236 Histamine receptor antagonist Drugs 0.000 description 3
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 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241000700159 Rattus Species 0.000 description 3
239000002253 acid Substances 0.000 description 3
229940125715 antihistaminic agent Drugs 0.000 description 3
239000000969 carrier Substances 0.000 description 3
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
230000027119 gastric acid secretion Effects 0.000 description 3
239000012362 glacial acetic acid Substances 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
238000010898 silica gel chromatography Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
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 2
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 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
LYIIBVSRGJSHAV-UHFFFAOYSA-N 2-aminoacetaldehyde Chemical compound NCC=O LYIIBVSRGJSHAV-UHFFFAOYSA-N 0.000 description 2
PFPJOYOZALIOIC-UHFFFAOYSA-N 2-methylsulfanyl-3-nitro-4-phenyl-1h-pyrrole Chemical compound [O-][N+](=O)C1=C(SC)NC=C1C1=CC=CC=C1 PFPJOYOZALIOIC-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
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
241000700199 Cavia porcellus Species 0.000 description 2
102000000543 Histamine Receptors Human genes 0.000 description 2
108010002059 Histamine Receptors Proteins 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
230000036772 blood pressure Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
CJXFSHWDLBBVSZ-UHFFFAOYSA-N ethyl 2-acetamido-3-oxoheptanoate Chemical compound CCCCC(=O)C(NC(C)=O)C(=O)OCC CJXFSHWDLBBVSZ-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000005764 inhibitory process Effects 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
ZGGDLECHSNKHJF-UHFFFAOYSA-N n-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-3-nitro-4-(2-phenylethyl)-1h-pyrrol-2-amine Chemical compound N1C=NC(CSCCNC2=C(C(CCC=3C=CC=CC=3)=CN2)[N+]([O-])=O)=C1C ZGGDLECHSNKHJF-UHFFFAOYSA-N 0.000 description 2
230000028327 secretion Effects 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 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
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
KYARXRLXUWJZKC-BTJKTKAUSA-N (z)-but-2-enedioic acid;4-butyl-n-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-3-nitro-1h-pyrrol-2-amine Chemical compound OC(=O)\C=C/C(O)=O.CCCCC1=CNC(NCCSCC2=C(NC=N2)C)=C1[N+]([O-])=O KYARXRLXUWJZKC-BTJKTKAUSA-N 0.000 description 1
NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-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
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
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
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 1
RUCLDQBBIJKQHO-UHFFFAOYSA-N 2-oxopropylazanium;chloride Chemical compound Cl.CC(=O)CN RUCLDQBBIJKQHO-UHFFFAOYSA-N 0.000 description 1
LOJNBPNACKZWAI-UHFFFAOYSA-N 3-nitro-1h-pyrrole Chemical compound [O-][N+](=O)C=1C=CNC=1 LOJNBPNACKZWAI-UHFFFAOYSA-N 0.000 description 1
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 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
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 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-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
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
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
108010079943 Pentagastrin Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 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
229930006000 Sucrose Natural products 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
125000006177 alkyl benzyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
230000031018 biological processes and functions Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 1
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
239000002775 capsule Substances 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
229960004926 chlorobutanol Drugs 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
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 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
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CNDRGQIPNUJNEQ-UHFFFAOYSA-N ethyl 2-acetyl-3-oxoheptanoate Chemical compound CCCCC(=O)C(C(C)=O)C(=O)OCC CNDRGQIPNUJNEQ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
230000002496 gastric effect Effects 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
210000002837 heart atrium Anatomy 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
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 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
239000008101 lactose Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
DFKGKEANDDNEPN-UHFFFAOYSA-N n-[2-[(3-chloropyridin-2-yl)methylsulfanyl]ethyl]-3-nitro-1h-pyrrol-2-amine Chemical compound C1=CNC(NCCSCC=2C(=CC=CN=2)Cl)=C1[N+](=O)[O-] DFKGKEANDDNEPN-UHFFFAOYSA-N 0.000 description 1
WSMQAYKMXMFXKP-UHFFFAOYSA-N n-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-3-nitro-1h-pyrrol-2-amine Chemical compound N1C=NC(CSCCNC2=C(C=CN2)[N+]([O-])=O)=C1C WSMQAYKMXMFXKP-UHFFFAOYSA-N 0.000 description 1
KRAPUWBZRULVHM-UHFFFAOYSA-N n-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-3-nitro-4-phenyl-1h-pyrrol-2-amine Chemical compound N1C=NC(CSCCNC2=C(C(=CN2)C=2C=CC=CC=2)[N+]([O-])=O)=C1C KRAPUWBZRULVHM-UHFFFAOYSA-N 0.000 description 1
UHBGFTIUCPXGIR-UHFFFAOYSA-N n-[2-[1-(1h-imidazol-5-yl)ethylsulfanyl]ethyl]-3-nitro-4-phenyl-1h-pyrrol-2-amine Chemical compound C=1NC=NC=1C(C)SCCNC(=C1[N+]([O-])=O)NC=C1C1=CC=CC=C1 UHBGFTIUCPXGIR-UHFFFAOYSA-N 0.000 description 1
DHYIGZBRHRKUJI-UHFFFAOYSA-N n-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-3-nitro-1h-pyrrol-2-amine Chemical compound O1C(CN(C)C)=CC=C1CSCCNC1=C([N+]([O-])=O)C=CN1 DHYIGZBRHRKUJI-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012299 nitrogen atmosphere 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
230000001151 other effect Effects 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
CVXGFPPAIUELDV-UHFFFAOYSA-N phenacylazanium;chloride Chemical compound [Cl-].[NH3+]CC(=O)C1=CC=CC=C1 CVXGFPPAIUELDV-UHFFFAOYSA-N 0.000 description 1
239000006187 pill 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
229940044551 receptor antagonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 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
238000010025 steaming Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

HUSI001695 1978-05-30 1979-05-29 Eljárás nitropirrol-származékok előállítására HU180082B (hu)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2411778		1978-05-30

Publications (1)

Publication Number	Publication Date
HU180082B true HU180082B (hu)	1983-01-28

Family

ID=10206663

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HUSI001695 HU180082B (hu)	1978-05-30	1979-05-29	Eljárás nitropirrol-származékok előállítására

Country Status (6)

Country	Link
JP (1)	JPS54157556A (cs)
AT (1)	AT375368B (cs)
CS (1)	CS228117B2 (cs)
HU (1)	HU180082B (cs)
SU (1)	SU1003755A3 (cs)
ZA (1)	ZA792607B (cs)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1419994A (en) *	1973-05-03	1976-01-07	Smith Kline French Lab	Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them
MW5076A1 (en) *	1975-12-29	1978-02-08	Smith Kline French Lab	Pharmacologicalle active compounds

1979
- 1979-05-28 ZA ZA792607A patent/ZA792607B/xx unknown
- 1979-05-29 HU HUSI001695 patent/HU180082B/hu unknown
- 1979-05-29 JP JP6740079A patent/JPS54157556A/ja active Pending
- 1979-05-29 SU SU792772805A patent/SU1003755A3/ru active
- 1979-05-30 AT AT395279A patent/AT375368B/de not_active IP Right Cessation
- 1979-05-30 CS CS372579A patent/CS228117B2/cs unknown

Also Published As

Publication number	Publication date
CS228117B2 (cs)	1984-05-14
AT375368B (de)	1984-07-25
JPS54157556A (en)	1979-12-12
SU1003755A3 (ru)	1983-03-07
ATA395279A (de)	1983-12-15
ZA792607B (en)	1980-07-30

Publication	Publication Date	Title
US4207324A (en)	1980-06-10	1,2-Di-Substituted-4-haloimidazole-5-acetic acid derivatives and their use
FI114983B (fi)	2005-02-15	Menetelmä bentsimidatsoli-7-karboksylaatin C-tyyppiä olevan kiteen valmistamiseksi
PT101875B (pt)	1999-04-30	Derivados de benzeno e processo para a sua preparacao
US4169154A (en)	1979-09-25	Method of treating depression with thiourea derivatives
EP0005984B1 (en)	1983-06-22	Nitro compounds, processes for preparing them and compositions containing them
US3868457A (en)	1975-02-25	Method of inhibiting histamine activity with guanidine compounds
EP0259930B1 (en)	1992-02-05	Derivatives of phenyl, pyrrolidin-2-yl substituted 5-ring heterocycles having antipsychotic properties
EP0005985B1 (en)	1983-04-27	3-nitro pyrrole compounds, processes for preparing them and pharmaceutical compositions containing them
US4066695A (en)	1978-01-03	Thiourea derivatives
USRE30457E (en)	1980-12-23	Pharmacologically active compounds
US4152453A (en)	1979-05-01	Pharmacologically active compounds and compositions and methods of use
IE44184B1 (en)	1981-09-09	Imidazole derivatives,processes for their preparation and pharmaceutical compositions containing them
US4584384A (en)	1986-04-22	Nitro pyrroles
US4113776A (en)	1978-09-12	1-(2-Aminoethyl)-3-(2,6-dihalophenyl)guanidines
US4150138A (en)	1979-04-17	Method of reducing blood pressure with thiourea derivatives and guanidine derivatives
EP0001266B1 (en)	1981-04-01	Substituted 2-aminomethylphenyl sulfamates, process for preparing, and pharmaceutical compositions containing the same
EP0278265B1 (en)	1992-09-09	1- [(4-Morpholinyl) alkyl] -1H-indoles useful as analgesics and preparation thereof
EP0156455A2 (en)	1985-10-02	Condensed seven-membered ring compounds, their production and use
EP0329691B1 (en)	1991-11-21	Cardiotonic imidazolylphenylpyrrol-2-ones
KR820001994B1 (ko)	1982-10-23	히스타민 h₂-수용체 길항작용을 가진 니트로 화합물의 제조방법
LU82823A1 (de)	1981-02-02	Neue 1,2,4-oxadiazin-derivate,ihre herstellung,bei ihrer herstellung anwendbare zwischenprodukte sowie pharmazeutische mittel
KR0160771B1 (ko)	1998-12-01	벤즈이미다졸 유도체, 그의 제조 및 용도
GB2063263A (en)	1981-06-03	A 1-isopropyl-4-phenyl-2(1H)- quinazolinone Derivative
CS228117B2 (cs)	1984-05-14	Způsob výroby derivátů 3-nitropyrrolu
IE51021B1 (en)	1986-09-03	1-aroyl-2-phenylamino-2-imidazolines,their preparation and drugs containing these compounds