IE41625B1 - Guanidine derivatives - Google Patents
Guanidine derivativesInfo
- Publication number
- IE41625B1 IE41625B1 IE1299/75A IE129975A IE41625B1 IE 41625 B1 IE41625 B1 IE 41625B1 IE 1299/75 A IE1299/75 A IE 1299/75A IE 129975 A IE129975 A IE 129975A IE 41625 B1 IE41625 B1 IE 41625B1
- Authority
- IE
- Ireland
- Prior art keywords
- methyl
- formula
- methylthio
- ethyl
- guanidine
- Prior art date
Links
- 150000002357 guanidines Chemical class 0.000 title abstract 2
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 239000000460 chlorine Substances 0.000 claims abstract description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005864 Sulphur Substances 0.000 claims abstract description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 4
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 150000003852 triazoles Chemical class 0.000 claims abstract description 3
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000003085 diluting agent Substances 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 24
- -1 4-methyl-5-imidazolyl Chemical group 0.000 claims description 16
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 12
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 6
- IGSAPGNIBICQPA-UHFFFAOYSA-N 2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CC=1NC=NC=1CSCCNC(N)=N IGSAPGNIBICQPA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 150000002541 isothioureas Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 abstract description 50
- 229960001340 histamine Drugs 0.000 abstract description 25
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- 230000000699 topical effect Effects 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 230000003042 antagnostic effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- CALVPZNSFFEPJG-UHFFFAOYSA-N guanidine;dihydrochloride Chemical compound Cl.Cl.NC(N)=N CALVPZNSFFEPJG-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- VJAMCQFRFWRULO-UHFFFAOYSA-N thiourea;dihydrochloride Chemical compound Cl.Cl.NC(S)=N VJAMCQFRFWRULO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 235000015497 potassium bicarbonate Nutrition 0.000 description 8
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 8
- 239000011736 potassium bicarbonate Substances 0.000 description 8
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- 230000031018 biological processes and functions Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- HXRBAVXGYZUSED-UHFFFAOYSA-N Burimamide Chemical compound CNC(=S)NCCCCC1=CN=CN1 HXRBAVXGYZUSED-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 229940125715 antihistaminic agent Drugs 0.000 description 4
- 239000000739 antihistaminic agent Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 239000011147 inorganic material Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003585 thioureas Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 229960000582 mepyramine Drugs 0.000 description 3
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- JLXDXEJQYISRAW-UHFFFAOYSA-N thiourea;trihydrochloride Chemical compound Cl.Cl.Cl.NC(S)=N JLXDXEJQYISRAW-UHFFFAOYSA-N 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 239000000969 carrier Substances 0.000 description 2
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 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
- ZGCHATBSUIJLRL-UHFFFAOYSA-N hydrazine sulfate Chemical compound NN.OS(O)(=O)=O ZGCHATBSUIJLRL-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
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- 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
- 125000004035 thiopropyl group Chemical group [H]SC([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-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
- JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 description 1
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-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
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- 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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- 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
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- IDJMDIVMAOGVJW-UHFFFAOYSA-N guanidine;trihydrochloride Chemical compound Cl.Cl.Cl.NC(N)=N IDJMDIVMAOGVJW-UHFFFAOYSA-N 0.000 description 1
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- ANNHTTPKZXOYQX-UHFFFAOYSA-N methyl n'-butyl-n-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate;dihydrochloride Chemical compound Cl.Cl.CCCCNC(SC)=NCCSCC=1NC=NC=1C ANNHTTPKZXOYQX-UHFFFAOYSA-N 0.000 description 1
- VEPHZPNAWUIXAU-UHFFFAOYSA-N methyl n'-methyl-n-[2-(1,3-thiazol-2-ylmethylsulfanyl)ethyl]carbamimidothioate;dihydrochloride Chemical compound Cl.Cl.CNC(SC)=NCCSCC1=NC=CS1 VEPHZPNAWUIXAU-UHFFFAOYSA-N 0.000 description 1
- RSJSMWFJRFLMNF-UHFFFAOYSA-N methyl n'-methyl-n-[3-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]propyl]carbamimidothioate;dihydrochloride Chemical compound Cl.Cl.CNC(SC)=NCCCSCC=1NC=NC=1C RSJSMWFJRFLMNF-UHFFFAOYSA-N 0.000 description 1
- BXXGTPDBOUVLLF-UHFFFAOYSA-N methyl n,n'-bis[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate;trihydrochloride Chemical compound Cl.Cl.Cl.N1=CNC(C)=C1CSCCN=C(SC)NCCSCC=1N=CNC=1C BXXGTPDBOUVLLF-UHFFFAOYSA-N 0.000 description 1
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- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
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- UOKZUTXLHRTLFH-UHFFFAOYSA-N o-phenylhydroxylamine Chemical compound NOC1=CC=CC=C1 UOKZUTXLHRTLFH-UHFFFAOYSA-N 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
- 239000002674 ointment Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000008188 pellet Substances 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
- 229960003975 potassium Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 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
- 239000008117 stearic acid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 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
- BNKMLRRKLVSLJN-UHFFFAOYSA-N tert-butyl n-amino-n-methylcarbamate;sulfuric acid Chemical compound OS(O)(=O)=O.CN(N)C(=O)OC(C)(C)C BNKMLRRKLVSLJN-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/26—Radicals substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB28722/74A GB1497260A (en) | 1974-06-28 | 1974-06-28 | Guanidine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41625L IE41625L (en) | 1975-12-28 |
| IE41625B1 true IE41625B1 (en) | 1980-02-13 |
Family
ID=10280055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1299/75A IE41625B1 (en) | 1974-06-28 | 1975-06-09 | Guanidine derivatives |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4034101A (en:Method) |
| JP (1) | JPS5946221B2 (en:Method) |
| AU (1) | AU503858B2 (en:Method) |
| BE (1) | BE830272A (en:Method) |
| CA (1) | CA1076579A (en:Method) |
| CH (1) | CH615669A5 (en:Method) |
| DE (1) | DE2528639A1 (en:Method) |
| DK (1) | DK268975A (en:Method) |
| ES (1) | ES438944A1 (en:Method) |
| FR (1) | FR2276042A1 (en:Method) |
| GB (1) | GB1497260A (en:Method) |
| IE (1) | IE41625B1 (en:Method) |
| IL (1) | IL47394A (en:Method) |
| LU (1) | LU72835A1 (en:Method) |
| NL (1) | NL7506951A (en:Method) |
| NO (1) | NO143942C (en:Method) |
| PH (1) | PH14275A (en:Method) |
| PL (1) | PL98616B1 (en:Method) |
| SE (1) | SE417961B (en:Method) |
| ZA (1) | ZA753455B (en:Method) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5014808U (en:Method) * | 1973-06-06 | 1975-02-17 | ||
| JPS55822B2 (en:Method) * | 1973-07-09 | 1980-01-10 | ||
| GB1493931A (en) * | 1974-02-07 | 1977-11-30 | Smith Kline French Lab | Guanidines isothioureas and thioureas |
| US4137319A (en) * | 1974-02-07 | 1979-01-30 | Smith Kline & French Laboratories Limited | Guanidino, thioureido, isothioureido and nitrovinylamino derivatives of pyridine |
| US4197305A (en) * | 1974-02-07 | 1980-04-08 | Smith Kline & French Laboratories Limited | Thiazole, isothiazole, oxazole and isoxazole compounds |
| GB1496787A (en) * | 1974-03-12 | 1978-01-05 | Smith Kline French Lab | Heteroalkylthioalkyl amidine derivatives |
| US4170652A (en) * | 1974-03-12 | 1979-10-09 | Smith Kline & French Laboratories Limited | Heterocyclic-methylthioalkyl-guanidines |
| JPS5912767Y2 (ja) * | 1974-03-28 | 1984-04-17 | アイワ カブシキガイシヤ | 回転機器の作動切換装置 |
| US4093729A (en) * | 1974-06-28 | 1978-06-06 | Smith Kline & French Laboratories Limited | N-Oxy and N-amino guanidines |
| IL49528A (en) * | 1975-05-21 | 1980-11-30 | Smith Kline French Lab | Imidazolyl(or thiazolyl)methylthio(or butyl)guanidine or thiourea derivatives,their preparation and pharmaceutical compositions comprising them |
| US4192879A (en) * | 1975-05-21 | 1980-03-11 | Smith Kline & French Laboratories Limited | Imidazolyl alkylamino nitroethylene compounds |
| GB1564502A (en) * | 1975-07-31 | 1980-04-10 | Smith Kline French Lab | Guanidines thioureas and 1,1-diamino-2-nitroethylene derivatives |
| NO781300L (no) | 1977-04-20 | 1978-10-23 | Ici Ltd | Fremgangsmaate for fremstilling av fysiologisk aktive guanidinderivater |
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| GB1602458A (en) * | 1977-05-05 | 1981-11-11 | Smith Kline French Lab | Bisamidines as histamine h2-antagonists |
| US4108859A (en) * | 1977-06-06 | 1978-08-22 | The Dow Chemical Company | Microbicidal (pyridinylamino) alkyl guanidines |
| US4233302A (en) | 1977-12-23 | 1980-11-11 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
| EP0006679B1 (en) | 1978-05-24 | 1982-07-21 | Imperial Chemical Industries Plc | Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| DE2966646D1 (en) * | 1978-10-16 | 1984-03-15 | Ici Plc | Antisecretory branched-chain heterocyclic guanidine derivatives, processes for their manufacture, intermediates, and pharmaceutical compositions containing said derivatives |
| DE3069889D1 (en) | 1979-01-18 | 1985-02-14 | Ici Plc | Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them |
| JPS56124143A (en) * | 1980-02-29 | 1981-09-29 | Sanyo Electric Co Ltd | Control mechanism of tape recorder |
| AU2222083A (en) * | 1982-12-14 | 1984-06-21 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
| JPS6156012U (en:Method) * | 1984-09-19 | 1986-04-15 | ||
| JPS61228914A (ja) * | 1985-04-04 | 1986-10-13 | Sumitomo Heavy Ind Ltd | 成形用金型 |
| US20230349922A1 (en) | 2020-08-11 | 2023-11-02 | Université De Strasbourg | H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758146A (fr) * | 1969-10-29 | 1971-04-28 | Smith Kline French Lab | Derives de l'amidine |
| GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
-
1974
- 1974-06-28 GB GB28722/74A patent/GB1497260A/en not_active Expired
-
1975
- 1975-05-28 ZA ZA00753455A patent/ZA753455B/xx unknown
- 1975-05-30 IL IL47394A patent/IL47394A/xx unknown
- 1975-06-09 IE IE1299/75A patent/IE41625B1/en unknown
- 1975-06-11 NL NL7506951A patent/NL7506951A/xx not_active Application Discontinuation
- 1975-06-11 US US05/585,898 patent/US4034101A/en not_active Expired - Lifetime
- 1975-06-12 CA CA229,222A patent/CA1076579A/en not_active Expired
- 1975-06-13 DK DK268975A patent/DK268975A/da not_active Application Discontinuation
- 1975-06-16 BE BE157354A patent/BE830272A/xx not_active IP Right Cessation
- 1975-06-20 PH PH17301A patent/PH14275A/en unknown
- 1975-06-20 AU AU82304/75A patent/AU503858B2/en not_active Ceased
- 1975-06-24 JP JP50079233A patent/JPS5946221B2/ja not_active Expired
- 1975-06-24 FR FR7519669A patent/FR2276042A1/fr active Granted
- 1975-06-26 DE DE19752528639 patent/DE2528639A1/de not_active Withdrawn
- 1975-06-26 SE SE7507364A patent/SE417961B/xx unknown
- 1975-06-26 LU LU72835A patent/LU72835A1/xx unknown
- 1975-06-27 CH CH838175A patent/CH615669A5/de not_active IP Right Cessation
- 1975-06-27 ES ES438944A patent/ES438944A1/es not_active Expired
- 1975-06-27 PL PL1975181592A patent/PL98616B1/pl unknown
- 1975-06-27 NO NO752330A patent/NO143942C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES438944A1 (es) | 1977-02-16 |
| PH14275A (en) | 1981-04-29 |
| AU503858B2 (en) | 1979-09-27 |
| JPS5119766A (en:Method) | 1976-02-17 |
| NO752330L (en:Method) | 1975-12-30 |
| LU72835A1 (en:Method) | 1975-10-08 |
| FR2276042B1 (en:Method) | 1980-04-25 |
| ZA753455B (en) | 1976-04-28 |
| SE417961B (sv) | 1981-04-27 |
| CA1076579A (en) | 1980-04-29 |
| GB1497260A (en) | 1978-01-05 |
| JPS5946221B2 (ja) | 1984-11-10 |
| DK268975A (da) | 1975-12-29 |
| BE830272A (fr) | 1975-12-16 |
| AU8230475A (en) | 1976-12-23 |
| US4034101A (en) | 1977-07-05 |
| CH615669A5 (en:Method) | 1980-02-15 |
| NO143942B (no) | 1981-02-02 |
| SE7507364L (sv) | 1975-12-29 |
| FR2276042A1 (fr) | 1976-01-23 |
| IE41625L (en) | 1975-12-28 |
| DE2528639A1 (de) | 1976-01-15 |
| PL98616B1 (pl) | 1978-05-31 |
| NL7506951A (nl) | 1975-12-30 |
| IL47394A0 (en) | 1975-07-28 |
| NO143942C (no) | 1981-05-13 |
| IL47394A (en) | 1980-01-31 |
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