NO762661L - - Google Patents
Info
- Publication number
- NO762661L NO762661L NO762661A NO762661A NO762661L NO 762661 L NO762661 L NO 762661L NO 762661 A NO762661 A NO 762661A NO 762661 A NO762661 A NO 762661A NO 762661 L NO762661 L NO 762661L
- Authority
- NO
- Norway
- Prior art keywords
- het
- formula
- lower alkyl
- sulfur
- ring
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 239000011593 sulfur Substances 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- JUJABTAZEDTRRH-UHFFFAOYSA-N CS(C)C(S)=NC#N Chemical compound CS(C)C(S)=NC#N JUJABTAZEDTRRH-UHFFFAOYSA-N 0.000 claims description 2
- VHTXENFHLDNTOH-UHFFFAOYSA-N C[SH](C)C(S)=NC(C1=CC=CC=C1)=O Chemical compound C[SH](C)C(S)=NC(C1=CC=CC=C1)=O VHTXENFHLDNTOH-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 229910017171 MNH2 Inorganic materials 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- GJEAMHAFPYZYDE-UHFFFAOYSA-N [C].[S] Chemical compound [C].[S] GJEAMHAFPYZYDE-UHFFFAOYSA-N 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- 239000000203 mixture Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 229960001340 histamine Drugs 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 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 6
- -1 dihydroxypyridine compound Chemical class 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- XTBZYMOXUSCADZ-UHFFFAOYSA-N 1-methylsulfanyl-1-methylsulfinyl-2-nitroethene Chemical group CSC(S(C)=O)=C[N+]([O-])=O XTBZYMOXUSCADZ-UHFFFAOYSA-N 0.000 description 5
- 239000002026 chloroform extract Substances 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- QGUQDIQQWVJQTG-UHFFFAOYSA-N 2-[(3-ethoxypyridin-2-yl)methylsulfanyl]ethanamine Chemical compound CCOC1=CC=CN=C1CSCCN QGUQDIQQWVJQTG-UHFFFAOYSA-N 0.000 description 3
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229940097265 cysteamine hydrochloride Drugs 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- QLAGECZOQRFYJG-UHFFFAOYSA-N (3-ethoxypyridin-2-yl)methanol Chemical compound CCOC1=CC=CN=C1CO QLAGECZOQRFYJG-UHFFFAOYSA-N 0.000 description 2
- RDXXAIGOEPIQPK-UHFFFAOYSA-N (3-methoxypyridin-2-yl)methanol Chemical compound COC1=CC=CN=C1CO RDXXAIGOEPIQPK-UHFFFAOYSA-N 0.000 description 2
- WDEGRDWGRKYVGC-UHFFFAOYSA-N 2-(chloromethyl)-3-ethoxypyridine;hydrochloride Chemical compound Cl.CCOC1=CC=CN=C1CCl WDEGRDWGRKYVGC-UHFFFAOYSA-N 0.000 description 2
- BVKOVRNDBVJWGM-UHFFFAOYSA-N 2-(chloromethyl)-3-methoxypyridine;hydrochloride Chemical compound Cl.COC1=CC=CN=C1CCl BVKOVRNDBVJWGM-UHFFFAOYSA-N 0.000 description 2
- PBDFBZPTRXMFBL-UHFFFAOYSA-N 2-(chloromethyl)-4-methoxypyridine;hydrochloride Chemical compound Cl.COC1=CC=NC(CCl)=C1 PBDFBZPTRXMFBL-UHFFFAOYSA-N 0.000 description 2
- ZJRBRKUGRKKZOO-UHFFFAOYSA-N 2-(hydroxymethyl)pyridin-3-ol Chemical compound OCC1=NC=CC=C1O ZJRBRKUGRKKZOO-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- BRARRAHGNDUELT-UHFFFAOYSA-N 3-hydroxypicolinic acid Chemical compound OC(=O)C1=NC=CC=C1O BRARRAHGNDUELT-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- MHKKUZDJUGIOBC-UHFFFAOYSA-N methyl 3-hydroxypyridine-2-carboxylate Chemical compound COC(=O)C1=NC=CC=C1O MHKKUZDJUGIOBC-UHFFFAOYSA-N 0.000 description 2
- LWBUORJYVJHZHR-UHFFFAOYSA-N methyl n-cyano-n'-[2-[(3-ethoxypyridin-2-yl)methylsulfanyl]ethyl]carbamimidothioate Chemical compound CCOC1=CC=CN=C1CSCCN=C(NC#N)SC LWBUORJYVJHZHR-UHFFFAOYSA-N 0.000 description 2
- KFGDUBBOFUPZMO-UHFFFAOYSA-N methyl n-cyano-n'-[2-[(4-methoxypyridin-2-yl)methylsulfanyl]ethyl]carbamimidothioate Chemical compound COC1=CC=NC(CSCCN=C(NC#N)SC)=C1 KFGDUBBOFUPZMO-UHFFFAOYSA-N 0.000 description 2
- MSZPCNXIUQPHSY-UHFFFAOYSA-N n-[2-[(3-methoxypyridin-2-yl)methylsulfanyl]ethyl]-1-methylsulfanyl-2-nitroethenamine Chemical group COC1=CC=CN=C1CSCCNC(SC)=C[N+]([O-])=O MSZPCNXIUQPHSY-UHFFFAOYSA-N 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- PKWDWPDWJICWDC-UHFFFAOYSA-N (3-methoxypyridin-2-yl)methanol;hydrochloride Chemical compound Cl.COC1=CC=CN=C1CO PKWDWPDWJICWDC-UHFFFAOYSA-N 0.000 description 1
- GBMRUSRMPOUVEK-UHFFFAOYSA-N (4-methoxypyridin-2-yl)methanol Chemical compound COC1=CC=NC(CO)=C1 GBMRUSRMPOUVEK-UHFFFAOYSA-N 0.000 description 1
- NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 1
- ZWZCQZCIZDUWOS-UHFFFAOYSA-N 1-methylsulfanyl-2-nitroethene Chemical group CSC=C[N+]([O-])=O ZWZCQZCIZDUWOS-UHFFFAOYSA-N 0.000 description 1
- OFPWMRMIFDHXFE-UHFFFAOYSA-N 2-(bromomethyl)pyridine Chemical class BrCC1=CC=CC=N1 OFPWMRMIFDHXFE-UHFFFAOYSA-N 0.000 description 1
- QPIYOAMUERYOML-UHFFFAOYSA-N 2-[(4-methoxypyridin-2-yl)methylsulfanyl]ethanamine;dihydrochloride Chemical compound Cl.Cl.COC1=CC=NC(CSCCN)=C1 QPIYOAMUERYOML-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 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
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 238000010934 O-alkylation reaction Methods 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- FKTUXVQEOXYNMO-UHFFFAOYSA-N cyanocarbamodithioic acid Chemical compound SC(=S)NC#N FKTUXVQEOXYNMO-UHFFFAOYSA-N 0.000 description 1
- SSGODMHQNTWPOX-UHFFFAOYSA-N cyanothiourea Chemical compound NC(=S)NC#N SSGODMHQNTWPOX-UHFFFAOYSA-N 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 210000004211 gastric acid Anatomy 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
- 229960000582 mepyramine Drugs 0.000 description 1
- KSXQRYUHBMAREL-UHFFFAOYSA-N methyl 3-methoxypyridine-2-carboxylate Chemical compound COC(=O)C1=NC=CC=C1OC KSXQRYUHBMAREL-UHFFFAOYSA-N 0.000 description 1
- GYOJFOIVPYHLNU-UHFFFAOYSA-N methyl 3-methoxypyridine-2-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1=NC=CC=C1OC GYOJFOIVPYHLNU-UHFFFAOYSA-N 0.000 description 1
- XYPUGPKLKOUKBB-UHFFFAOYSA-N methyl n-cyano-n'-[2-[(3-methoxypyridin-2-yl)methylsulfanyl]ethyl]carbamimidothioate Chemical compound COC1=CC=CN=C1CSCCN=C(NC#N)SC XYPUGPKLKOUKBB-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CCGDGIVOYLQECJ-UHFFFAOYSA-N n-[2-[(3-ethoxypyridin-2-yl)methylsulfanyl]ethyl]-1-methylsulfanyl-2-nitroethenamine Chemical group CCOC1=CC=CN=C1CSCCNC(SC)=C[N+]([O-])=O CCGDGIVOYLQECJ-UHFFFAOYSA-N 0.000 description 1
- YLCPELUEPPNOIT-UHFFFAOYSA-N n-[2-[(4-methoxypyridin-2-yl)methylsulfanyl]ethyl]-1-methylsulfanyl-2-nitroethenamine Chemical group COC1=CC=NC(CSCCNC(SC)=C[N+]([O-])=O)=C1 YLCPELUEPPNOIT-UHFFFAOYSA-N 0.000 description 1
- YMYKTMQVPCWDJJ-UHFFFAOYSA-N n-[2-[(4-methoxypyridin-2-yl)methylsulfanyl]ethyl]-1-methylsulfanyl-2-nitroethenamine;hydrate Chemical compound O.COC1=CC=NC(CSCCNC(SC)=C[N+]([O-])=O)=C1 YMYKTMQVPCWDJJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical class OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
- KEYZUMLVDCHSTP-UHFFFAOYSA-N pyridin-2-ylmethyl acetate Chemical class CC(=O)OCC1=CC=CC=N1 KEYZUMLVDCHSTP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
Classifications
-
- 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB31970/75A GB1564502A (en) | 1975-07-31 | 1975-07-31 | Guanidines thioureas and 1,1-diamino-2-nitroethylene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO762661L true NO762661L (fi) | 1977-02-01 |
Family
ID=10331105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO762661A NO762661L (fi) | 1975-07-31 | 1976-07-30 |
Country Status (31)
| Country | Link |
|---|---|
| US (4) | US4083983A (fi) |
| JP (2) | JPS5219671A (fi) |
| AR (1) | AR213736A1 (fi) |
| AT (1) | AT356132B (fi) |
| AU (1) | AU502752B2 (fi) |
| BE (1) | BE844504A (fi) |
| BG (1) | BG27368A3 (fi) |
| CA (1) | CA1068711A (fi) |
| CH (1) | CH624938A5 (fi) |
| CS (1) | CS189018B2 (fi) |
| DD (1) | DD125204A5 (fi) |
| DE (1) | DE2634433A1 (fi) |
| DK (1) | DK316176A (fi) |
| ES (1) | ES450310A1 (fi) |
| FI (1) | FI762193A (fi) |
| FR (1) | FR2319343A1 (fi) |
| GB (1) | GB1564502A (fi) |
| GR (1) | GR60810B (fi) |
| HU (1) | HU173778B (fi) |
| IE (1) | IE43508B1 (fi) |
| IL (1) | IL50005A (fi) |
| LU (1) | LU75507A1 (fi) |
| NL (1) | NL7608496A (fi) |
| NO (1) | NO762661L (fi) |
| PH (1) | PH14555A (fi) |
| PL (1) | PL103684B1 (fi) |
| PT (1) | PT65348B (fi) |
| SE (1) | SE7608477L (fi) |
| SU (1) | SU692558A3 (fi) |
| ZA (1) | ZA764082B (fi) |
| ZM (1) | ZM9876A1 (fi) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4928863A (fi) * | 1972-07-13 | 1974-03-14 | ||
| JPS5078968U (fi) * | 1973-11-20 | 1975-07-08 | ||
| ZA774220B (en) * | 1976-07-28 | 1978-06-28 | Smith Kline French Lab | Pharmacologically active compounds |
| ZA782129B (en) | 1977-04-20 | 1979-03-28 | Ici Ltd | Hertocyclic derivatives |
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| US4233302A (en) * | 1977-12-23 | 1980-11-11 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
| US4282363A (en) * | 1978-11-24 | 1981-08-04 | Bristol-Myers Company | 1-Nitro-2-(2-alkynylamino)-2-[(2-pyridylmethylthio)-ethylamino]ethylene derivatives |
| US4250316A (en) * | 1978-11-24 | 1981-02-10 | Bristol-Myers Company | Pyridyl guanidine anti-ulcer agents |
| US4287346A (en) * | 1979-02-16 | 1981-09-01 | Eisai Co., Ltd. | Cyanoguanidine derivatives |
| PT74865B (en) * | 1981-05-27 | 1983-12-07 | Smithkline Beckman Corp | Process of preparing a 2-(pyridylbutylamino)-pyrimidone and of its pharmaceutically acceptable salts |
| SE8204879D0 (sv) * | 1982-08-26 | 1982-08-26 | Haessle Ab | Novel chemical intermediates |
| DE3232462A1 (de) * | 1982-09-01 | 1984-03-01 | Bayer Ag, 5090 Leverkusen | 2-nitro-1,1-ethendiamine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| JPH0828166B2 (ja) * | 1985-01-16 | 1996-03-21 | 松下電器産業株式会社 | サ−モスタツト |
| AU660132B2 (en) * | 1992-12-21 | 1995-06-08 | Bayer Aktiengesellschaft | Substituted 4-phenyl-pyridones and 4-phenyl-2-alkoxypyridine |
| US5380734A (en) * | 1993-04-15 | 1995-01-10 | American Home Products Corporation | N-cyanoamidine derivatives as anti-influenza agents |
| AU2019295853A1 (en) | 2018-06-29 | 2021-01-14 | 410 Medical, Inc. | Systems, apparatus, and methods for filtering air from a fluid line |
| WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3968216A (en) * | 1969-10-29 | 1976-07-06 | Smith Kline & French Laboratories Limited | Method of inhibiting histamine activity with guanidine compounds |
| US3808336A (en) | 1970-06-25 | 1974-04-30 | Smithkline Corp | Pharmaceutical compositions and methods of inhibiting histamine activity with thiourea derivatives |
| US3908014A (en) * | 1970-06-25 | 1975-09-23 | Smith Kline French Lab | Pharmaceutical compositions and methods of inhibiting histamine activity with thiourea derivatives |
| GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
| US3905984A (en) * | 1971-03-09 | 1975-09-16 | Smith Kline French Lab | Pyridyl substituted thioalkyl-and oxyalkyl-thioureas and ureas |
| GB1397436A (en) * | 1972-09-05 | 1975-06-11 | Smith Kline French Lab | Heterocyclic n-cyanoguinidines |
| GB1421792A (en) * | 1973-05-17 | 1976-01-21 | Smith Kline French Lab | Heterocyclic substituted-1, 1-diamino-ethylene derivatives methods for their preparation and compositions containing them |
| US4002759A (en) * | 1973-05-17 | 1977-01-11 | Smith Kline & French Laboratories Limited | Pyridylbutylamino ethylene compounds |
| US4025527A (en) * | 1973-07-13 | 1977-05-24 | Smith Kline & French Laboratories Limited | Certain thiazoles and oxazoles |
| GB1497260A (en) * | 1974-06-28 | 1978-01-05 | Smith Kline French Lab | Guanidine derivatives |
-
1975
- 1975-07-31 GB GB31970/75A patent/GB1564502A/en not_active Expired
-
1976
- 1976-07-09 ZA ZA764082A patent/ZA764082B/xx unknown
- 1976-07-09 PT PT65348A patent/PT65348B/pt unknown
- 1976-07-09 PH PH18668A patent/PH14555A/en unknown
- 1976-07-09 IL IL50005A patent/IL50005A/xx unknown
- 1976-07-13 US US05/704,877 patent/US4083983A/en not_active Expired - Lifetime
- 1976-07-13 DK DK316176A patent/DK316176A/da unknown
- 1976-07-21 CS CS764841A patent/CS189018B2/cs unknown
- 1976-07-22 CA CA257,590A patent/CA1068711A/en not_active Expired
- 1976-07-23 ZM ZM98/76A patent/ZM9876A1/xx unknown
- 1976-07-23 BE BE169228A patent/BE844504A/xx not_active IP Right Cessation
- 1976-07-27 GR GR51358A patent/GR60810B/el unknown
- 1976-07-27 SE SE7608477A patent/SE7608477L/xx not_active Application Discontinuation
- 1976-07-27 AT AT552576A patent/AT356132B/de not_active IP Right Cessation
- 1976-07-30 AR AR264159A patent/AR213736A1/es active
- 1976-07-30 SU SU762386151A patent/SU692558A3/ru active
- 1976-07-30 LU LU75507A patent/LU75507A1/xx unknown
- 1976-07-30 JP JP51092245A patent/JPS5219671A/ja active Pending
- 1976-07-30 NL NL7608496A patent/NL7608496A/xx not_active Application Discontinuation
- 1976-07-30 ES ES450310A patent/ES450310A1/es not_active Expired
- 1976-07-30 AU AU16453/76A patent/AU502752B2/en not_active Expired
- 1976-07-30 HU HU76SI1531A patent/HU173778B/hu unknown
- 1976-07-30 NO NO762661A patent/NO762661L/no unknown
- 1976-07-30 FI FI762193A patent/FI762193A/fi not_active Application Discontinuation
- 1976-07-30 DD DD194159A patent/DD125204A5/xx unknown
- 1976-07-30 CH CH978576A patent/CH624938A5/de not_active IP Right Cessation
- 1976-07-30 BG BG7633887A patent/BG27368A3/xx unknown
- 1976-07-30 IE IE1708/76A patent/IE43508B1/en unknown
- 1976-07-30 FR FR7623453A patent/FR2319343A1/fr active Granted
- 1976-07-30 DE DE19762634433 patent/DE2634433A1/de not_active Withdrawn
- 1976-07-30 PL PL1976191537A patent/PL103684B1/pl unknown
-
1979
- 1979-02-21 US US06/013,579 patent/US4215126A/en not_active Expired - Lifetime
- 1979-11-15 US US06/094,412 patent/US4264608A/en not_active Expired - Lifetime
-
1980
- 1980-11-19 US US06/208,370 patent/US4426526A/en not_active Expired - Lifetime
-
1985
- 1985-02-25 JP JP60037341A patent/JPS60243069A/ja active Granted
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