NO762661L - - Google Patents

Info

Publication number: NO762661L
Authority: NO; Norway
Prior art keywords: het; formula; lower alkyl; sulfur; ring
Prior art date: 1975-07-31

Application number

NO762661A

Other languages

English (en)

Norwegian (no)

Inventor

G J Durant

G S Sach

C R Ganellin

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

1977-02-01

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

1977-02-01 Publication of NO762661L publication Critical patent/NO762661L/no

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

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)

NO762661A 1975-07-31 1976-07-30 NO762661L (mo)

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 (mo)	1977-02-01

Family

ID=10331105

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO762661A NO762661L (mo)	1975-07-31	1976-07-30

Country Status (31)

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

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4928863A (mo) *	1972-07-13	1974-03-14
JPS5078968U (mo) *	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 (mo)	1977-02-01
CA1068711A (en)	1979-12-25
JPS617423B2 (mo)	1986-03-06
US4215126A (en)	1980-07-29
ATA552576A (de)	1979-09-15
DD125204A5 (mo)	1977-04-06
CH624938A5 (mo)	1981-08-31
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 (mo)	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 (mo)	1977-03-03
JPS5219671A (en)	1977-02-15
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

Publication	Publication Date	Title
US4013678A (en)	1977-03-22	Process for preparing heterocyclicalkylthioalkyl-n-cyanoguanidines
DK1797037T3 (en)	2015-03-30	PROCESS FOR THE PREPARATION OF 4- {4 - [({[4-chloro-3- (trifluoromethyl) phenyl] AMINO} CARBONYL) AMINO] PHENYOXY} N-methylpyridine-2-carboxamide
NO120426B (mo)	1970-10-19
US4083983A (en)	1978-04-11	Alkoxy pyridine compounds
FI63573C (fi)	1985-05-15	Foerfarande foer framstaellning av oxibensotiazin-dioxiders kaboxamider
NO145236B (no)	1981-11-02	Analogifremgangsmaate ved fremstilling av terapeutisk aktive omega-aminocarboxylsyrederivater
CN117120436A (zh)	2023-11-24	一种一步法合成乙内酰硫脲衍生物的方法
IL33292A (en)	1973-04-30	Amino and imino derivatives of thiazolines,thiazolidines and thiazines,their preparation and pharmaceutical compositions containing them
Zinnes et al.	1973	1, 2-Benzothiazines. 6. 3-Carbamoyl-4-hydroxy-2H-1, 2-benzothiazine 1, 1-dioxides as antiinflammatory agents
NO762659L (mo)	1977-02-01
NO764039L (mo)	1977-06-06
NO151348B (no)	1984-12-17	Trikot stroempebukse og fremgangsmaate for fremstilling av samme
WO2023160634A1 (zh)	2023-08-31	苯并噻唑类化合物、其制备方法及应用
EP1042292A1 (en)	2000-10-11	Method for producing isoureas
NO770161L (no)	1977-07-21	Tiazolidinderivater og fremgangsm}te til deres fremstilling.
JP3413632B2 (ja)	2003-06-03	グアニジン誘導体の製造方法
US4093621A (en)	1978-06-06	Process for preparing heterocyclicalkylthioalkyl-N-cyanoguanidines and thioureas
JPH0449539B2 (mo)	1992-08-11
US2569415A (en)	1951-09-25	Imidazolines
NO803160L (no)	1978-08-07	Pyrimidin-derivater.
NO784350L (no)	1979-07-03	Fremgangsmaate til alkylering av 4(5)-merkaptometyl-imidazoler med aziridinderivater
US4226799A (en)	1980-10-07	α-Aminomethylene-β-formylaminopropionitrile and its manufacture
SU1227111A3 (ru)	1986-04-23	Способ получени производных гуанидина или их таутомерных соединений или их солей
NO165248B (no)	1990-10-08	Kammervegg for anvendelse i en konverter for behandling av stoepejernsmelter.
SU449485A3 (ru)	1974-11-05	Способ получени -замещенных сложных эфиров 1,2,3,6-тетрагидро-4пиридилметилкарбоновой кислоты