IE47275B1 - Amidines - Google Patents

Amidines

Info

Publication number: IE47275B1
Authority: IE; Ireland
Prior art keywords: methyl; hydrogen; het; compound according; compound
Prior art date: 1977-06-02

Application number

IE110078A

Other languages

English (en)

Other versions

IE781100L (en

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

1978-05-31

Publication date

1984-02-08

1978-05-31 Application filed by Smith Kline French Lab filed Critical Smith Kline French Lab

1978-12-02 Publication of IE781100L publication Critical patent/IE781100L/xx

1984-02-08 Publication of IE47275B1 publication Critical patent/IE47275B1/en

Links

150000001409 amidines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 60
-1 Amidine phosphonate compounds Chemical class 0.000 claims abstract description 55
125000000217 alkyl group Chemical group 0.000 claims abstract description 42
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
239000001257 hydrogen Substances 0.000 claims abstract description 40
125000003118 aryl group Chemical group 0.000 claims abstract description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
150000002431 hydrogen Chemical group 0.000 claims abstract description 12
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
239000005864 Sulphur Substances 0.000 claims abstract description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
238000000034 method Methods 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical group 0.000 claims description 8
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
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 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000000623 heterocyclic group Chemical group 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
238000004519 manufacturing process Methods 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000002883 imidazolyl group Chemical group 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
150000001721 carbon Chemical group 0.000 claims description 2
230000000295 complement effect Effects 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
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
150000003852 triazoles Chemical class 0.000 claims description 2
239000008024 pharmaceutical diluent Substances 0.000 claims 2
230000001419 dependent effect Effects 0.000 claims 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
239000011574 phosphorus Substances 0.000 claims 1
230000007062 hydrolysis Effects 0.000 abstract description 11
238000006460 hydrolysis reaction Methods 0.000 abstract description 11
239000004480 active ingredient Substances 0.000 abstract description 7
238000005859 coupling reaction Methods 0.000 abstract description 5
239000000543 intermediate Substances 0.000 abstract description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 5
230000000694 effects Effects 0.000 abstract description 4
238000002360 preparation method Methods 0.000 abstract description 3
239000003485 histamine H2 receptor antagonist Substances 0.000 abstract description 2
238000005954 phosphonylation reaction Methods 0.000 abstract 1
150000003141 primary amines Chemical class 0.000 abstract 1
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 52
239000002253 acid Substances 0.000 description 44
239000003153 chemical reaction reagent Substances 0.000 description 30
229960001340 histamine Drugs 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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 15
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 14
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
239000000460 chlorine Substances 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 7
239000005557 antagonist Substances 0.000 description 7
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
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
230000031018 biological processes and functions Effects 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
150000005690 diesters Chemical class 0.000 description 6
239000000203 mixture Substances 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
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
229910000042 hydrogen bromide Inorganic materials 0.000 description 5
239000007788 liquid Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical class 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
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
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
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
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
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
239000000739 antihistaminic agent Substances 0.000 description 3
229940125715 antihistaminic agent Drugs 0.000 description 3
235000010290 biphenyl Nutrition 0.000 description 3
239000004305 biphenyl Substances 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000004615 ingredient 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
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-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
IXFKWSLOVDXTFU-UHFFFAOYSA-N 2-(1,3-oxazol-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=NC=CO1 IXFKWSLOVDXTFU-UHFFFAOYSA-N 0.000 description 2
CNMUGSJVSYLQOX-UHFFFAOYSA-N 2-(1h-imidazol-5-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=CNC=N1 CNMUGSJVSYLQOX-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
VJSUMPPMFYQOMP-UHFFFAOYSA-N 4-(1h-imidazol-5-yl)butan-1-amine Chemical compound NCCCCC1=CNC=N1 VJSUMPPMFYQOMP-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
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
235000021355 Stearic acid Nutrition 0.000 description 2
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 2
229930006000 Sucrose Natural products 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
150000001412 amines Chemical class 0.000 description 2
229940107816 ammonium iodide Drugs 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
WJOZHMLTXAXJGX-UHFFFAOYSA-N chloro(3-phenylpropoxy)phosphinic acid Chemical compound OP(Cl)(=O)OCCCC1=CC=CC=C1 WJOZHMLTXAXJGX-UHFFFAOYSA-N 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
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
239000007903 gelatin capsule Substances 0.000 description 2
210000002837 heart atrium Anatomy 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
239000003112 inhibitor Substances 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
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
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 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
239000008117 stearic acid Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 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
LPKCJFLRJWWIDI-UHFFFAOYSA-N (diaminomethylideneamino)phosphonic acid Chemical class NC(N)=NP(O)(O)=O LPKCJFLRJWWIDI-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
QEBVWWWCJJNGRP-UHFFFAOYSA-N 2-(1,3,4-thiadiazol-2-ylmethylsulfanyl)ethanamine Chemical compound NCCSCC1=NN=CS1 QEBVWWWCJJNGRP-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
HTABEAIBEITBJS-UHFFFAOYSA-N 2-[(3-chloropyridin-2-yl)methylsulfanyl]ethanamine Chemical compound NCCSCC1=NC=CC=C1Cl HTABEAIBEITBJS-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
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
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
BFMROWFYXXUHGE-UHFFFAOYSA-N CNC(=N)P(O)(O)=O Chemical class CNC(=N)P(O)(O)=O BFMROWFYXXUHGE-UHFFFAOYSA-N 0.000 description 1
101150106671 COMT gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
102000000543 Histamine Receptors Human genes 0.000 description 1
108010002059 Histamine Receptors Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010061218 Inflammation Diseases 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
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
208000001871 Tachycardia Diseases 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
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
125000004104 aryloxy group Chemical group 0.000 description 1
MRKFHQKLPMGVJD-UHFFFAOYSA-N benzyl phenyl hydrogen phosphite Chemical compound C=1C=CC=CC=1OP(O)OCC1=CC=CC=C1 MRKFHQKLPMGVJD-UHFFFAOYSA-N 0.000 description 1
125000001743 benzylic group Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
125000004432 carbon atom Chemical group C* 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
239000003795 chemical substances by application 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
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
LXHWDUISRBUGRA-UHFFFAOYSA-N dichloro(phenoxy)phosphane Chemical compound ClP(Cl)OC1=CC=CC=C1 LXHWDUISRBUGRA-UHFFFAOYSA-N 0.000 description 1
TXFOLHZMICYNRM-UHFFFAOYSA-N dichlorophosphoryloxybenzene Chemical compound ClP(Cl)(=O)OC1=CC=CC=C1 TXFOLHZMICYNRM-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000118 dimethyl group Chemical group [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
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
FICLVKKYNDVHDG-UHFFFAOYSA-N ethanamine;dihydrobromide Chemical compound Br.Br.CCN FICLVKKYNDVHDG-UHFFFAOYSA-N 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
LFXAECSQJSRSTP-UHFFFAOYSA-N hydron;methyl carbamimidothioate;iodide Chemical compound I.CSC(N)=N LFXAECSQJSRSTP-UHFFFAOYSA-N 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
229930189585 ingamine Natural products 0.000 description 1
230000010354 integration Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
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
150000002689 maleic acids Chemical class 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
LGVXHBNICWGKGM-UHFFFAOYSA-N n-(n-methyl-c-methylsulfanylcarbonimidoyl)-(3-phenylpropoxy)phosphonamidic acid Chemical compound CNC(SC)=NP(O)(=O)OCCCC1=CC=CC=C1 LGVXHBNICWGKGM-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-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
229960000444 pentagastrin Drugs 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical class [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
150000003018 phosphorus compounds Chemical class 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
125000004076 pyridyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 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
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IE110078A 1977-06-02 1978-05-31 Amidines IE47275B1 (en)

Applications Claiming Priority (2)

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

Publications (2)

Publication Number	Publication Date
IE781100L IE781100L (en)	1978-12-02
IE47275B1 true IE47275B1 (en)	1984-02-08

Family

ID=26256502

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE110078A IE47275B1 (en)	1977-06-02	1978-05-31	Amidines

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
AU2019423646B2 (en)	2019-01-23	2025-01-09	Kabushiki Kaisha Toshiba	Power supply system and method for controlling power supply system

1978
- 1978-05-30 ZA ZA00783118A patent/ZA783118B/xx unknown
- 1978-05-30 FI FI781714A patent/FI781714A7/fi not_active Application Discontinuation
- 1978-05-31 IE IE110078A patent/IE47275B1/en unknown
- 1978-05-31 AU AU36746/78A patent/AU514526B2/en not_active Expired
- 1978-06-01 IT IT7824126A patent/IT7824126A0/it unknown
- 1978-06-01 HU HUSI001630 patent/HU177898B/hu unknown
- 1978-06-01 CA CA304,575A patent/CA1096384A/en not_active Expired
- 1978-06-01 DK DK245078A patent/DK245078A/da unknown
- 1978-06-01 IL IL54832A patent/IL54832A/xx unknown
- 1978-06-01 NO NO781914A patent/NO781914L/no 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
IL54832A0 (en)	1978-08-31
CA1096384A (en)	1981-02-24
IE781100L (en)	1978-12-02
JPS543068A (en)	1979-01-11
DK245078A (da)	1978-12-03
ATA403078A (de)	1982-04-15
AT369013B (de)	1982-11-25
IL54832A (en)	1983-07-31
IT7824126A0 (it)	1978-06-01
AU3674678A (en)	1979-12-06
ZA783118B (en)	1979-06-27
AU514526B2 (en)	1981-02-12
FI781714A7 (fi)	1978-12-03
NO781914L (no)	1978-12-05
HU177898B (en)	1982-01-28

Publication	Publication Date	Title
KR0156239B1 (ko)	1998-12-01	헤테로 사이클릭 비스포스폰산 유도체 및 이의 제조방법
US4876248A (en)	1989-10-24	Anti-inflammatory products derived from methylene-diphosphonic acid, and process for their preparation
KR100366727B1 (ko)	2003-03-15	포스포네이트뉴클레오티드화합물
US4939130A (en)	1990-07-03	Substituted alkanediphosphonic acids and pharmaceutical use
CA1296739C (en)	1992-03-03	Diphosphonic acid derivatives, processes for the preparation thereofand pharmaceutical compositions containing them
KR970005179B1 (ko)	1997-04-14	(사이클로알킬아미노)메틸렌비스(포스폰산) 및 활성 성분으로서 이를 함유하는 약제
Stawinski et al.	1990	Nucleoside H-phosphonates. 12. Synthesis of nucleoside 3'-(hydrogen phosphonothioate) monoesters via phosphinate intermediates
KR20020093824A (ko)	2002-12-16	포스포네이트 뉴클레오티드 화합물
EP0070433A1 (de)	1983-01-26	Phospholipide Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
US4732998A (en)	1988-03-22	Bisphosphonic acids and esters
Woster et al.	1989	Synthesis and biological evaluation of S-adenosyl-1, 12-diamino-3-thio-9-azadodecane, a multisubstrate adduct inhibitor of spermine synthase
EP0337706A1 (de)	1989-10-18	Substituierte Aminomethylenbisphosphonsäure Derivate
PL144353B1 (en)	1988-05-31	Method of obtaining novel derivatives of methylenediophosphonic acid
IE47275B1 (en)	1984-02-08	Amidines
EP0007326B1 (de)	1982-01-27	Amidine, deren Herstellung und diese Amidine enthaltende pharmazeutische Zusammensetzungen.
US4190664A (en)	1980-02-26	Amidino and guanidino phosphonates
US4282213A (en)	1981-08-04	Amidino and guanidino phosphonates
US5155099A (en)	1992-10-13	Alkylphosphonoserines and pharmaceutical compositions useful as cytostatic agents
US5245069A (en)	1993-09-14	Process for the preparation of bis(aryl)-phosphorohalidates
US4845261A (en)	1989-07-04	Process for bis(substituted phenyl) phosphorohalidates
GB1565647A (en)	1980-04-23	Pharmacologically active compounds 4-substituted-imidazole-5-methanols
EP0518861A1 (de)	1992-12-23	Verfahren zur gewinnung von phosphorigsäure-bis-(2,4-di-tert.-butyl-phenyl)-ester-halogeniden.
JPH0699457B2 (ja)	1994-12-07	ヘテロ環ビスフォスフォン酸誘導体およびその医薬
US6407029B1 (en)	2002-06-18	Mixtures comprising tetrakis(pyrrolidino/piperdino)phosphonium salts
US6444847B2 (en)	2002-09-03	Process for preparing phosphine oxides and process for purifying the same