NO781914L - Fremgangsmaate for fremstilling av amidiner - Google Patents

Fremgangsmaate for fremstilling av amidiner

Info

Publication number: NO781914L
Authority: NO; Norway
Prior art keywords: lower alkyl; aryl; methyl; hydrogen; compound
Prior art date: 1977-06-02

Application number

NO781914A

Other languages

English (en)

Norwegian (no)

Inventor

Graham John Durant

Rodney Christopher Young

Zev Tashma

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.)

1977-06-02

Filing date

1978-06-01

Publication date

1978-12-05

1978-06-01 Application filed by Smith Kline French Lab filed Critical Smith Kline French Lab

1978-12-05 Publication of NO781914L publication Critical patent/NO781914L/no

Links

238000000034 method Methods 0.000 title claims description 45
238000002360 preparation method Methods 0.000 title description 8
150000001409 amidines Chemical class 0.000 title description 2
238000006243 chemical reaction Methods 0.000 claims description 45
150000001875 compounds Chemical class 0.000 claims description 43
125000000217 alkyl group Chemical group 0.000 claims description 41
-1 primary amino compound Chemical class 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 30
125000003118 aryl group Chemical group 0.000 claims description 28
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
239000007858 starting material Substances 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 5
238000004519 manufacturing process Methods 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
229910052717 sulfur Inorganic materials 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
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
229910052799 carbon Inorganic materials 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
230000000295 complement effect Effects 0.000 claims description 2
125000002883 imidazolyl group 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
150000003852 triazoles Chemical class 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000000463 material Substances 0.000 claims 2
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 36
239000002253 acid Substances 0.000 description 29
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
229960001340 histamine Drugs 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 12
239000000243 solution Substances 0.000 description 12
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
230000007062 hydrolysis Effects 0.000 description 10
238000006460 hydrolysis reaction Methods 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
150000005690 diesters Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
230000004071 biological effect Effects 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
108020003175 receptors Proteins 0.000 description 5
238000003756 stirring Methods 0.000 description 5
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
229910000042 hydrogen bromide Inorganic materials 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
LPKCJFLRJWWIDI-UHFFFAOYSA-N (diaminomethylideneamino)phosphonic acid Chemical class NC(N)=NP(O)(O)=O LPKCJFLRJWWIDI-UHFFFAOYSA-N 0.000 description 3
ITAMCOCNZJPJDF-UHFFFAOYSA-N 1-(6-aminopurin-9-yl)propan-2-yloxymethyl-phenoxyphosphinic acid Chemical compound C1=NC2=C(N)N=CN=C2N1CC(C)OCP(O)(=O)OC1=CC=CC=C1 ITAMCOCNZJPJDF-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
102000003710 Histamine H2 Receptors Human genes 0.000 description 3
108090000050 Histamine H2 Receptors Proteins 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
239000000739 antihistaminic agent Substances 0.000 description 3
229940125715 antihistaminic agent Drugs 0.000 description 3
RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 3
WJOZHMLTXAXJGX-UHFFFAOYSA-N chloro(3-phenylpropoxy)phosphinic acid Chemical compound OP(Cl)(=O)OCCCC1=CC=CC=C1 WJOZHMLTXAXJGX-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000003480 eluent Substances 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
230000001404 mediated effect Effects 0.000 description 3
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
YZBOZNXACBQJHI-UHFFFAOYSA-N 1-dichlorophosphoryloxyethane Chemical compound CCOP(Cl)(Cl)=O YZBOZNXACBQJHI-UHFFFAOYSA-N 0.000 description 2
GKIUPDRWOXMZDT-UHFFFAOYSA-N 2-(1,2-thiazol-3-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC=1C=CSN=1 GKIUPDRWOXMZDT-UHFFFAOYSA-N 0.000 description 2
QEBVWWWCJJNGRP-UHFFFAOYSA-N 2-(1,3,4-thiadiazol-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=NN=CS1 QEBVWWWCJJNGRP-UHFFFAOYSA-N 0.000 description 2
IXFKWSLOVDXTFU-UHFFFAOYSA-N 2-(1,3-oxazol-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=NC=CO1 IXFKWSLOVDXTFU-UHFFFAOYSA-N 0.000 description 2
BUTQLNVJGRJSAE-UHFFFAOYSA-N 2-(1h-1,2,4-triazol-5-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC=1N=CNN=1 BUTQLNVJGRJSAE-UHFFFAOYSA-N 0.000 description 2
XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 2
HTABEAIBEITBJS-UHFFFAOYSA-N 2-[(3-chloropyridin-2-yl)methylsulfanyl]ethanamine Chemical compound NCCSCC1=NC=CC=C1Cl HTABEAIBEITBJS-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
241000700199 Cavia porcellus Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
UDUMWDDMSHXGGQ-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-methylazanium;iodide Chemical compound I.CSC(N)=NC UDUMWDDMSHXGGQ-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
229940107816 ammonium iodide Drugs 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
210000004211 gastric acid Anatomy 0.000 description 2
230000027119 gastric acid secretion Effects 0.000 description 2
210000002837 heart atrium Anatomy 0.000 description 2
239000003485 histamine H2 receptor antagonist Substances 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
239000003112 inhibitor Substances 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
YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 2
229960000582 mepyramine Drugs 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000028327 secretion Effects 0.000 description 2
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
JBGXWNBKQNLZOP-UHFFFAOYSA-N 1-[ethoxy(phenylmethoxy)phosphoryl]-2,3-bis[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound C=1C=CC=CC=1COP(=O)(OCC)NC(=NCCSCC1=C(NC=N1)C)NCCSCC=1N=CNC=1C JBGXWNBKQNLZOP-UHFFFAOYSA-N 0.000 description 1
WAIHMWWSWLOHNH-UHFFFAOYSA-N 2-(1,3-thiazol-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=NC=CS1 WAIHMWWSWLOHNH-UHFFFAOYSA-N 0.000 description 1
YJGPAHTYRHCODQ-UHFFFAOYSA-N 2-(1,3-thiazol-2-ylmethylsulfanyl)ethanamine;dihydrobromide Chemical compound Br.Br.NCCSCC1=NC=CS1 YJGPAHTYRHCODQ-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
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
HYSZRUJKUKKFRL-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]propan-1-amine Chemical compound NCC(C)SCC=1N=CNC=1C HYSZRUJKUKKFRL-UHFFFAOYSA-N 0.000 description 1
MTIMDGQILFWMJI-UHFFFAOYSA-N 2-methylsulfanyl-4,5-dihydro-1h-imidazole Chemical compound CSC1=NCCN1 MTIMDGQILFWMJI-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
VJSUMPPMFYQOMP-UHFFFAOYSA-N 4-(1h-imidazol-5-yl)butan-1-amine Chemical compound NCCCCC1=CNC=N1 VJSUMPPMFYQOMP-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
235000006491 Acacia senegal Nutrition 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
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235000021355 Stearic acid Nutrition 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
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CMALSAKGWMXXGV-UHFFFAOYSA-N [[N'-methyl-N-[2-(1,3,4-thiadiazol-2-ylmethylsulfanyl)ethyl]carbamimidoyl]amino]phosphonic acid Chemical compound OP(=O)(O)NC(=NC)NCCSCC1=NN=CS1 CMALSAKGWMXXGV-UHFFFAOYSA-N 0.000 description 1
GPEGHMAERWEZIX-UHFFFAOYSA-N [[n'-methyl-n-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethyl]carbamimidoyl]amino]phosphonic acid Chemical compound OP(=O)(O)NC(=NC)NCCSCC1=NC=CS1 GPEGHMAERWEZIX-UHFFFAOYSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 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
125000004414 alkyl thio group Chemical group 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000003708 ampul Substances 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
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238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
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239000012467 final product Substances 0.000 description 1
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230000003116 impacting effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000010354 integration Effects 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
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150000002540 isothiocyanates Chemical class 0.000 description 1
150000002541 isothioureas Chemical class 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
OPGQGYQPVOWUOO-UHFFFAOYSA-N methyl n'-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NCCSCC=1N=CNC=1C OPGQGYQPVOWUOO-UHFFFAOYSA-N 0.000 description 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
IHJFGFWDSZKVOV-UHFFFAOYSA-N n-[n'-methyl-n-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidoyl]-phenylmethoxyphosphonamidic acid;hydrobromide Chemical compound Br.C=1C=CC=CC=1COP(O)(=O)NC(=NC)NCCSCC=1N=CNC=1C IHJFGFWDSZKVOV-UHFFFAOYSA-N 0.000 description 1
ALANAUUPVXUEEO-UHFFFAOYSA-N n-[n-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-c-methylsulfanylcarbonimidoyl]-(3-phenylpropoxy)phosphonamidic acid Chemical compound C=1C=CC=CC=1CCCOP(O)(=O)N=C(SC)NCCSCC=1N=CNC=1C ALANAUUPVXUEEO-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 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
125000000962 organic group Chemical group 0.000 description 1
239000003960 organic solvent Substances 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
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ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical class [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
125000001918 phosphonic acid ester group Chemical group 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000006794 tachycardia Effects 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
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 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)

NO781914A 1977-06-02 1978-06-01 Fremgangsmaate for fremstilling av amidiner NO781914L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB2342377		1977-06-02
GB3911877		1977-09-20

Publications (1)

Publication Number	Publication Date
NO781914L true NO781914L (no)	1978-12-05

Family

ID=26256502

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO781914A NO781914L (no)	1977-06-02	1978-06-01	Fremgangsmaate for fremstilling av amidiner

Country Status (12)

Country	Link
JP (1)	JPS543068A (de)
AT (1)	AT369013B (de)
AU (1)	AU514526B2 (de)
CA (1)	CA1096384A (de)
DK (1)	DK245078A (de)
FI (1)	FI781714A7 (de)
HU (1)	HU177898B (de)
IE (1)	IE47275B1 (de)
IL (1)	IL54832A (de)
IT (1)	IT7824126A0 (de)
NO (1)	NO781914L (de)
ZA (1)	ZA783118B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE53068B1 (en) *	1981-06-15	1988-05-25	Merck & Co Inc	Diamino isothiazole-1-oxides and -1,1-dioxides as gastic secretion inhibitors
JP7068507B2 (ja)	2019-01-23	2022-05-16	株式会社東芝	電力供給システム、及び電力供給システムの制御方法

1978
- 1978-05-30 FI FI781714A patent/FI781714A7/fi not_active Application Discontinuation
- 1978-05-30 ZA ZA00783118A patent/ZA783118B/xx unknown
- 1978-05-31 AU AU36746/78A patent/AU514526B2/en not_active Expired
- 1978-05-31 IE IE110078A patent/IE47275B1/en unknown
- 1978-06-01 IL IL54832A patent/IL54832A/xx unknown
- 1978-06-01 CA CA304,575A patent/CA1096384A/en not_active Expired
- 1978-06-01 IT IT7824126A patent/IT7824126A0/it unknown
- 1978-06-01 DK DK245078A patent/DK245078A/da unknown
- 1978-06-01 NO NO781914A patent/NO781914L/no unknown
- 1978-06-01 HU HUSI001630 patent/HU177898B/hu unknown
- 1978-06-02 AT AT403078A patent/AT369013B/de not_active IP Right Cessation
- 1978-06-02 JP JP6716978A patent/JPS543068A/ja active Pending

Also Published As

Publication number	Publication date
IE781100L (en)	1978-12-02
FI781714A7 (fi)	1978-12-03
HU177898B (en)	1982-01-28
AU3674678A (en)	1979-12-06
AU514526B2 (en)	1981-02-12
DK245078A (da)	1978-12-03
JPS543068A (en)	1979-01-11
AT369013B (de)	1982-11-25
ZA783118B (en)	1979-06-27
ATA403078A (de)	1982-04-15
IL54832A (en)	1983-07-31
IE47275B1 (en)	1984-02-08
CA1096384A (en)	1981-02-24
IL54832A0 (en)	1978-08-31
IT7824126A0 (it)	1978-06-01

Publication	Publication Date	Title
US4939130A (en)	1990-07-03	Substituted alkanediphosphonic acids and pharmaceutical use
US4876248A (en)	1989-10-24	Anti-inflammatory products derived from methylene-diphosphonic acid, and process for their preparation
KR0156239B1 (ko)	1998-12-01	헤테로 사이클릭 비스포스폰산 유도체 및 이의 제조방법
KR850001795B1 (ko)	1985-12-21	2,4-이치환된 티아졸 유도체의 제조방법
DE69415436T2 (de)	1999-06-02	Phosphonsäure diester-derivate
DE69503904T2 (de)	1999-04-22	Phosphinsaeurederivate mit metallopeptidase inhibtorischer wirkung
CZ281983B6 (cs)	1997-04-16	Imidazolové deriváty s bočním bifenylsulfonylmočovinovým nebo bifenylsulfonylurethanovým řetězcem, způsob přípravy těchto derivátů a farmaceutická kompozice tyto deriváty obsahující
EP0040696A2 (de)	1981-12-02	Aminothiadiazole als gastrische Inhibitoren
HU198033B (en)	1989-07-28	Process for production of n-benzhydril-diaz-cycloalkilalcane-anilides and medical preparatives containing these compounds as active substance
WO1996001267A1 (en)	1996-01-18	Phosphonic acid compounds, their production and use
WO1999062892A1 (en)	1999-12-09	Aminoazole compounds
DD144057A5 (de)	1980-09-24	Verfahren zur herstellung von als histamin h tief 2-rezeptor-antagonisten wirkenden nitroverbindungen
DE2604056A1 (de)	1976-08-05	Thiocarbaminsaeure-derivate
NO781914L (no)	1978-12-05	Fremgangsmaate for fremstilling av amidiner
NO762659L (de)	1977-02-01
EP0007326B1 (de)	1982-01-27	Amidine, deren Herstellung und diese Amidine enthaltende pharmazeutische Zusammensetzungen.
NO134421B (de)	1976-06-28
US4190664A (en)	1980-02-26	Amidino and guanidino phosphonates
US4282213A (en)	1981-08-04	Amidino and guanidino phosphonates
EP0005985B1 (de)	1983-04-27	3-Nitro-pyrrol-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
NO781572L (no)	1978-11-07	Fremgangsmaate for fremstilling av bisamidiner
EP1012152B1 (de)	2002-10-09	Verfahren zur herstellung von oxazaphosphorin-2-aminen
US5382671A (en)	1995-01-17	Process for the preparation of 2-chloro-5-alkylaminomethyl-pyridines
DE3701209C2 (de)	1990-12-20
EP0083186A2 (de)	1983-07-06	Thiazolderivate als H2-Rezeptor-Antagonisten