CH624938A5 - - Google Patents

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Publication number: CH624938A5
Authority: CH; Switzerland
Prior art keywords: group; general formula; methylthio; pyridyl; radical
Prior art date: 1975-07-31

Application number

CH978576A

Other languages

German (de)

English (en)

Inventor

Graham John Durant

Charon Robin Ganellin

George Sidney Sach

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.)

1975-07-31

Filing date

1976-07-30

Publication date

1981-08-31

1976-07-30 Application filed by Smith Kline French Lab filed Critical Smith Kline French Lab

1981-08-31 Publication of CH624938A5 publication Critical patent/CH624938A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 61
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 23
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
150000001412 amines Chemical class 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 13
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
125000004434 sulfur atom Chemical group 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
125000004432 carbon atom Chemical group C* 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
229910017171 MNH2 Inorganic materials 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000001786 isothiazolyl group Chemical group 0.000 claims description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
150000003672 ureas Chemical class 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 94
239000000243 solution Substances 0.000 description 58
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
-1 alkyl radical Chemical class 0.000 description 40
239000000203 mixture Substances 0.000 description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 24
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 24
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
229960001340 histamine Drugs 0.000 description 12
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 11
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
239000002244 precipitate Substances 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
229910000041 hydrogen chloride Inorganic materials 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
VGMZAKKUIGITCD-UHFFFAOYSA-N 2-[(3-methoxypyridin-2-yl)methylsulfanyl]ethanamine Chemical compound COC1=CC=CN=C1CSCCN VGMZAKKUIGITCD-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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
241000700159 Rattus Species 0.000 description 6
239000002026 chloroform extract Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
XMLZZXNLTIVKDH-UHFFFAOYSA-N 4-(3-methoxypyridin-2-yl)butan-1-amine Chemical compound COC1=CC=CN=C1CCCCN XMLZZXNLTIVKDH-UHFFFAOYSA-N 0.000 description 5
IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 5
VMLPSMNOEMCPJX-UHFFFAOYSA-N (4-amino-3-methoxypyridin-2-yl)methanol Chemical compound COC1=C(N)C=CN=C1CO VMLPSMNOEMCPJX-UHFFFAOYSA-N 0.000 description 4
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 4
OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
102000003710 Histamine H2 Receptors Human genes 0.000 description 4
108090000050 Histamine H2 Receptors Proteins 0.000 description 4
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
150000001204 N-oxides Chemical class 0.000 description 4
239000000969 carrier Substances 0.000 description 4
229940097265 cysteamine hydrochloride Drugs 0.000 description 4
230000027119 gastric acid secretion Effects 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000007787 solid Substances 0.000 description 4
125000000446 sulfanediyl group Chemical group *S* 0.000 description 4
ZJRBRKUGRKKZOO-UHFFFAOYSA-N 2-(hydroxymethyl)pyridin-3-ol Chemical compound OCC1=NC=CC=C1O ZJRBRKUGRKKZOO-UHFFFAOYSA-N 0.000 description 3
QGUQDIQQWVJQTG-UHFFFAOYSA-N 2-[(3-ethoxypyridin-2-yl)methylsulfanyl]ethanamine Chemical compound CCOC1=CC=CN=C1CSCCN QGUQDIQQWVJQTG-UHFFFAOYSA-N 0.000 description 3
UTOYOMYYDAWZBO-UHFFFAOYSA-N 3-methoxy-2-methyl-4-nitro-1-oxidopyridin-1-ium Chemical compound COC1=C(C)[N+]([O-])=CC=C1[N+]([O-])=O UTOYOMYYDAWZBO-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-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
239000000739 antihistaminic agent Substances 0.000 description 3
229940125715 antihistaminic agent Drugs 0.000 description 3
230000004071 biological effect Effects 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
239000003814 drug Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 3
229960000582 mepyramine Drugs 0.000 description 3
238000010992 reflux Methods 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
HUCPKOBYKCQNJA-UHFFFAOYSA-N 1-[2-[(3-chloro-4-methoxypyridin-2-yl)methylsulfanyl]ethyl]-3-cyano-2-methylguanidine Chemical compound COC1=CC=NC(CSCCNC(NC#N)=NC)=C1Cl HUCPKOBYKCQNJA-UHFFFAOYSA-N 0.000 description 2
JFQAGNPRVSKXEX-UHFFFAOYSA-N 1-cyano-3-[4-(3-methoxypyridin-2-yl)butyl]-2-methylguanidine Chemical compound COC1=CC=CN=C1CCCCNC(NC#N)=NC JFQAGNPRVSKXEX-UHFFFAOYSA-N 0.000 description 2
ZYLHKRZUWUOJRX-UHFFFAOYSA-N 1-n'-[2-[(3-methoxypyridin-2-yl)methylsulfanyl]ethyl]-1-n-methyl-2-nitroethene-1,1-diamine Chemical group [O-][N+](=O)C=C(NC)NCCSCC1=NC=CC=C1OC ZYLHKRZUWUOJRX-UHFFFAOYSA-N 0.000 description 2
XHWDFGQAXHSIMH-UHFFFAOYSA-N 2-(bromomethyl)-6-methoxypyridine Chemical compound COC1=CC=CC(CBr)=N1 XHWDFGQAXHSIMH-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
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
AQSRRZGQRFFFGS-UHFFFAOYSA-N 2-methylpyridin-3-ol Chemical compound CC1=NC=CC=C1O AQSRRZGQRFFFGS-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
NESFDGDRYVANBC-UHFFFAOYSA-N 6-(hydroxymethyl)pyridin-3-ol Chemical compound OCC1=CC=C(O)C=N1 NESFDGDRYVANBC-UHFFFAOYSA-N 0.000 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 description 2
241000700199 Cavia porcellus Species 0.000 description 2
102000000543 Histamine Receptors Human genes 0.000 description 2
108010002059 Histamine Receptors Proteins 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000007903 gelatin capsule Substances 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
MHKKUZDJUGIOBC-UHFFFAOYSA-N methyl 3-hydroxypyridine-2-carboxylate Chemical compound COC(=O)C1=NC=CC=C1O MHKKUZDJUGIOBC-UHFFFAOYSA-N 0.000 description 2
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 2
229910017604 nitric acid Inorganic materials 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
150000003222 pyridines Chemical class 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
FLKNGCUAIIWFEX-UHFFFAOYSA-N (3-chloro-4-methoxypyridin-2-yl)methanol Chemical compound COC1=CC=NC(CO)=C1Cl FLKNGCUAIIWFEX-UHFFFAOYSA-N 0.000 description 1
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
ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
RMHLXIYZDUHAKE-UHFFFAOYSA-N 1-[2-[(3-methoxypyridin-2-yl)methylsulfanyl]ethyl]-2-methylguanidine Chemical compound CNC(=N)NCCSCC1=NC=CC=C1OC RMHLXIYZDUHAKE-UHFFFAOYSA-N 0.000 description 1
JYAIKOITNZHLGU-UHFFFAOYSA-N 1-[2-[(4-amino-3-methoxypyridin-2-yl)methylsulfanyl]ethyl]-3-cyano-2-methylguanidine Chemical compound COC1=C(N)C=CN=C1CSCCNC(NC#N)=NC JYAIKOITNZHLGU-UHFFFAOYSA-N 0.000 description 1
CFTRKVRHCBQSBH-UHFFFAOYSA-N 1-[4-(3-methoxypyridin-2-yl)butyl]-3-methylthiourea Chemical compound CNC(=S)NCCCCC1=NC=CC=C1OC CFTRKVRHCBQSBH-UHFFFAOYSA-N 0.000 description 1
MMYKTRPLXXWLBC-UHFFFAOYSA-N 1-bromo-2-ethoxyethane Chemical compound CCOCCBr MMYKTRPLXXWLBC-UHFFFAOYSA-N 0.000 description 1
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
PAJLIUWNAOJZIP-UHFFFAOYSA-N 1-cyano-1,2-bis[2-[(3-methoxypyridin-2-yl)methylsulfanyl]ethyl]guanidine Chemical compound COC1=CC=CN=C1CSCCNC(=N)N(C#N)CCSCC1=NC=CC=C1OC PAJLIUWNAOJZIP-UHFFFAOYSA-N 0.000 description 1
CIMYCGBRRSAKJJ-UHFFFAOYSA-N 1-cyano-3-[2-[(3,4-dimethoxypyridin-2-yl)methylsulfanyl]ethyl]-2-methylguanidine Chemical compound COC1=CC=NC(CSCCNC(NC#N)=NC)=C1OC CIMYCGBRRSAKJJ-UHFFFAOYSA-N 0.000 description 1
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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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH978576A 1975-07-31 1976-07-30 CH624938A5 (th)

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
CH624938A5 true CH624938A5 (th)	1981-08-31

Family

ID=10331105

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH978576A CH624938A5 (th)	1975-07-31	1976-07-30

Country Status (31)

Country	Link
US (4)	US4083983A (th)
JP (2)	JPS5219671A (th)
AR (1)	AR213736A1 (th)
AT (1)	AT356132B (th)
AU (1)	AU502752B2 (th)
BE (1)	BE844504A (th)
BG (1)	BG27368A3 (th)
CA (1)	CA1068711A (th)
CH (1)	CH624938A5 (th)
CS (1)	CS189018B2 (th)
DD (1)	DD125204A5 (th)
DE (1)	DE2634433A1 (th)
DK (1)	DK316176A (th)
ES (1)	ES450310A1 (th)
FI (1)	FI762193A7 (th)
FR (1)	FR2319343A1 (th)
GB (1)	GB1564502A (th)
GR (1)	GR60810B (th)
HU (1)	HU173778B (th)
IE (1)	IE43508B1 (th)
IL (1)	IL50005A (th)
LU (1)	LU75507A1 (th)
NL (1)	NL7608496A (th)
NO (1)	NO762661L (th)
PH (1)	PH14555A (th)
PL (1)	PL103684B1 (th)
PT (1)	PT65348B (th)
SE (1)	SE7608477L (th)
SU (1)	SU692558A3 (th)
ZA (1)	ZA764082B (th)
ZM (1)	ZM9876A1 (th)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4928863A (th) *	1972-07-13	1974-03-14
JPS5078968U (th) *	1973-11-20	1975-07-08
ZA774220B (en) *	1976-07-28	1978-06-28	Smith Kline French Lab	Pharmacologically active compounds
US4165378A (en)	1977-04-20	1979-08-21	Ici Americas Inc.	Guanidine derivatives of imidazoles and thiazoles
NZ186965A (en)	1977-04-20	1980-02-21	Ici Ltd	Guanidino derivatives and pharmaceutical compositions
US4233302A (en) *	1977-12-23	1980-11-11	Glaxo Group Limited	Amine derivatives and pharmaceutical compositions containing them
US4250316A (en) *	1978-11-24	1981-02-10	Bristol-Myers Company	Pyridyl guanidine anti-ulcer agents
US4282363A (en) *	1978-11-24	1981-08-04	Bristol-Myers Company	1-Nitro-2-(2-alkynylamino)-2-[(2-pyridylmethylthio)-ethylamino]ethylene derivatives
EP0014057B1 (en)	1979-01-18	1985-01-02	Imperial Chemical Industries Plc	Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them
NL8000869A (nl) *	1979-02-16	1980-08-19	Eisai Co Ltd	Cyanoguanidine-derivaten en werkwijze voor de bereiding daarvan.
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
AU2019295853B2 (en)	2018-06-29	2025-05-08	410 Medical, Inc.	Systems, apparatus, and methods for filtering air from a fluid line
EP4196793A1 (en)	2020-08-11	2023-06-21	Université de Strasbourg	H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer

Family Cites Families (10)

* Cited by examiner, † Cited by third party
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
US3908014A (en) *	1970-06-25	1975-09-23	Smith Kline French Lab	Pharmaceutical compositions and methods of inhibiting histamine activity with thiourea derivatives
US3808336A (en)	1970-06-25	1974-04-30	Smithkline Corp	Pharmaceutical compositions and methods of inhibiting histamine activity with thiourea derivatives
US3905984A (en) *	1971-03-09	1975-09-16	Smith Kline French Lab	Pyridyl substituted thioalkyl-and oxyalkyl-thioureas and ureas
GB1338169A (en) *	1971-03-09	1973-11-21	Smith Kline French Lab	Ureas thioureas and guanidines
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 PT PT65348A patent/PT65348B/pt unknown
- 1976-07-09 IL IL50005A patent/IL50005A/xx unknown
- 1976-07-09 PH PH18668A patent/PH14555A/en unknown
- 1976-07-09 ZA ZA764082A patent/ZA764082B/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 BE BE169228A patent/BE844504A/xx not_active IP Right Cessation
- 1976-07-23 ZM ZM98/76A patent/ZM9876A1/xx unknown
- 1976-07-27 GR GR51358A patent/GR60810B/el unknown
- 1976-07-27 AT AT552576A patent/AT356132B/de not_active IP Right Cessation
- 1976-07-27 SE SE7608477A patent/SE7608477L/xx not_active Application Discontinuation
- 1976-07-30 NL NL7608496A patent/NL7608496A/xx not_active Application Discontinuation
- 1976-07-30 JP JP51092245A patent/JPS5219671A/ja active Pending
- 1976-07-30 AR AR264159A patent/AR213736A1/es active
- 1976-07-30 CH CH978576A patent/CH624938A5/de not_active IP Right Cessation
- 1976-07-30 DE DE19762634433 patent/DE2634433A1/de not_active Withdrawn
- 1976-07-30 IE IE1708/76A patent/IE43508B1/en unknown
- 1976-07-30 PL PL1976191537A patent/PL103684B1/pl unknown
- 1976-07-30 FR FR7623453A patent/FR2319343A1/fr active Granted
- 1976-07-30 HU HU76SI1531A patent/HU173778B/hu unknown
- 1976-07-30 DD DD194159A patent/DD125204A5/xx unknown
- 1976-07-30 ES ES450310A patent/ES450310A1/es not_active Expired
- 1976-07-30 FI FI762193A patent/FI762193A7/fi not_active Application Discontinuation
- 1976-07-30 BG BG033887A patent/BG27368A3/xx unknown
- 1976-07-30 SU SU762386151A patent/SU692558A3/ru active
- 1976-07-30 AU AU16453/76A patent/AU502752B2/en not_active Expired
- 1976-07-30 LU LU75507A patent/LU75507A1/xx unknown
- 1976-07-30 NO NO762661A patent/NO762661L/no 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

Also Published As

Publication number	Publication date
SU692558A3 (ru)	1979-10-15
BE844504A (fr)	1977-01-24
NL7608496A (nl)	1977-02-02
BG27368A3 (bg)	1979-10-12
ES450310A1 (es)	1977-12-01
PH14555A (en)	1981-09-24
DE2634433A1 (de)	1977-02-03
PT65348B (en)	1978-01-06
AT356132B (de)	1980-04-10
PL103684B1 (pl)	1979-07-31
PT65348A (en)	1976-08-01
FI762193A7 (th)	1977-02-01
CA1068711A (en)	1979-12-25
JPS617423B2 (th)	1986-03-06
US4215126A (en)	1980-07-29
ATA552576A (de)	1979-09-15
DD125204A5 (th)	1977-04-06
CS189018B2 (en)	1979-03-30
AR213736A1 (es)	1979-03-15
AU1645376A (en)	1978-02-02
ZA764082B (en)	1977-06-29
GB1564502A (en)	1980-04-10
FR2319343A1 (fr)	1977-02-25
FR2319343B1 (th)	1978-11-17
IL50005A (en)	1981-06-29
IE43508L (en)	1977-01-31
ZM9876A1 (en)	1977-09-21
SE7608477L (sv)	1977-02-01
DK316176A (da)	1977-02-01
JPS60243069A (ja)	1985-12-03
LU75507A1 (th)	1977-03-03
JPS5219671A (en)	1977-02-15
NO762661L (th)	1977-02-01
IL50005A0 (en)	1976-09-30
US4426526A (en)	1984-01-17
IE43508B1 (en)	1981-03-11
US4264608A (en)	1981-04-28
HU173778B (hu)	1979-08-28
AU502752B2 (en)	1979-08-09
GR60810B (en)	1978-08-30
US4083983A (en)	1978-04-11

Legal Events

Date	Code	Title	Description
1985-03-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0001279B1 (de)	1981-09-30	Imidazolderivate deren Herstellung und diese enthaltende Präparate
DE2344779A1 (de)	1974-03-14	Cyanguanidine, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CH624941A5 (th)	1981-08-31
DE2643670C2 (de)	1982-07-01	5-Benzyl-4-pyrimidon-Derivate, ihre Salze mit Säuren, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2406166A1 (de)	1974-08-15	Sulfoxide, ihre salze mit saeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2634433A1 (de)	1977-02-03	Harnstoffderivate, ihre salze mit saeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2634429A1 (de)	1977-02-10	Cyclobutendion- und -dithionderivate, ihre salze mit saeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2433625A1 (de)	1975-01-30	Harnstoff-derivate, verfahren zu ihrer herstellung und arzneimittel
DE2658267A1 (de)	1977-07-07	Pyrimid-4-on- und -thion-derivate, ihre salze mit saeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2847792C2 (th)	1988-02-04
DE2344833A1 (de)	1974-03-14	Guanidine, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DD149217A5 (de)	1981-07-01	Verfahren zur herstellung von pyrimidonderivaten
DE2411295A1 (de)	1974-09-19	Substituierte benzimidazol-2-carbamatderivate, verfahren zu deren herstellung und diese enthaltende zusammensetzung
DE2604056A1 (de)	1976-08-05	Thiocarbaminsaeure-derivate
DE1643279A1 (de)	1971-06-09	Aromatische Sulfamoylverbindungen
DE2710326A1 (de)	1977-09-15	Amidinoameisen- und -sulfinsaeurederivate, ihre hydrate und salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
US4156727A (en)	1979-05-29	Alkoxy pyridine compounds
DE2634430A1 (de)	1977-02-10	Harnstoffderivate, ihre salze mit saeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0177054B1 (de)	1989-02-08	Neue Pyridinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE2634432A1 (de)	1977-02-10	Sulfoxide, ihre salze mit saeuren, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0160173B1 (de)	1989-06-14	Benzothiazolderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltendes Arzneimittel
CH640540A5 (de)	1984-01-13	Thieno-thiazinderivate.
DE2811477A1 (de)	1978-09-21	1,2,4-triazin-5-on-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2733952A1 (de)	1978-02-02	Alpha, omega-diaminoalkylenverbindungen
DE2733953A1 (de)	1978-02-02	Alpha,omega-diaminoalkylenverbindungen