CS244411B2 - Způsob pHpravy 3.4-diamino-1,2,5-thiadiazolových derivátů - Google Patents

Způsob pHpravy 3.4-diamino-1,2,5-thiadiazolových derivátů Download PDF

Info

Publication number: CS244411B2
Authority: CS; Czechoslovakia
Prior art keywords: amino; thiadiazole; oxide; carbon atoms; ethyl
Prior art date: 1980-04-30

Application number

CS813166A

Other languages

Czech (cs)

English (en)

Other versions

CS316681A2 (en

Inventor

John J Baldvin

William A Bolhofer

William C Limma

Joseph S Amato

Sandor Karady

Leonard M Weinstock

Original Assignee

Merck & Co Inc

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.)

1980-04-30

Filing date

1981-04-28

Publication date

1986-07-17

1981-04-28 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1985-09-17 Publication of CS316681A2 publication Critical patent/CS316681A2/cs

1986-07-17 Publication of CS244411B2 publication Critical patent/CS244411B2/cs

Links

238000002360 preparation method Methods 0.000 title claims description 22
-1 carbon ethers Chemical class 0.000 claims description 111
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 81
150000001875 compounds Chemical class 0.000 claims description 67
125000004432 carbon atom Chemical group C* 0.000 claims description 40
QLKJZSNKNPNUNN-UHFFFAOYSA-N 1-oxo-1,2,5-thiadiazole-3,4-diamine Chemical compound NC1=NS(=O)N=C1N QLKJZSNKNPNUNN-UHFFFAOYSA-N 0.000 claims description 29
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 29
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
238000000034 method Methods 0.000 claims description 27
150000001412 amines Chemical class 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
150000002431 hydrogen Chemical group 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
239000011593 sulfur Substances 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000004076 pyridyl group Chemical group 0.000 claims description 9
IPLXKLUYTPGIPL-UHFFFAOYSA-N 1,2,5-thiadiazole-3,4-diamine Chemical class NC1=NSN=C1N IPLXKLUYTPGIPL-UHFFFAOYSA-N 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000000623 heterocyclic group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000002883 imidazolyl group Chemical group 0.000 claims description 5
125000000547 substituted alkyl group Chemical group 0.000 claims description 5
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
239000000010 aprotic solvent Substances 0.000 claims description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
125000006715 (C1-C5) alkylthio group Chemical group 0.000 claims 1
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 86
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 69
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 67
239000000243 solution Substances 0.000 description 63
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
239000000047 product Substances 0.000 description 49
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
239000000203 mixture Substances 0.000 description 33
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
239000007787 solid Substances 0.000 description 29
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 22
YGTYZVFDTDFSDN-UHFFFAOYSA-N 4-ethoxy-1-oxo-1,2,5-thiadiazol-3-amine Chemical compound CCOC1=NS(=O)N=C1N YGTYZVFDTDFSDN-UHFFFAOYSA-N 0.000 description 18
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 16
239000002904 solvent Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000000725 suspension Substances 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 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
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
239000000126 substance Substances 0.000 description 9
WWEIMDRGLPALKY-UHFFFAOYSA-N 3,4-diethoxy-1,2,5-thiadiazole 1-oxide Chemical compound CCOC1=NS(=O)N=C1OCC WWEIMDRGLPALKY-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
239000013078 crystal Substances 0.000 description 8
239000000284 extract Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
SQPAODNXQWZASE-UHFFFAOYSA-N 4-ethoxy-n-methyl-1-oxo-1,2,5-thiadiazol-3-amine Chemical compound CCOC1=NS(=O)N=C1NC SQPAODNXQWZASE-UHFFFAOYSA-N 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 7
239000012043 crude product Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
LGLWJSHIGIZSIK-UHFFFAOYSA-N 3-n-methyl-1-oxo-1,2,5-thiadiazole-3,4-diamine Chemical compound CNC1=NS(=O)N=C1N LGLWJSHIGIZSIK-UHFFFAOYSA-N 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
239000002585 base Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 5
230000002496 gastric effect Effects 0.000 description 5
229960001340 histamine Drugs 0.000 description 5
239000000463 material Substances 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 5
239000000376 reactant Substances 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
241000282472 Canis lupus familiaris Species 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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238000001914 filtration Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
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229910000029 sodium carbonate Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
AGTBVIJJZHVPEY-UHFFFAOYSA-N 1,1-dioxo-1,2,5-thiadiazole-3,4-diamine Chemical group NC1=NS(=O)(=O)N=C1N AGTBVIJJZHVPEY-UHFFFAOYSA-N 0.000 description 3
YEGXJMUBOQLVDV-UHFFFAOYSA-N 1-(6-chloropyridin-2-yl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=CC(Cl)=N1 YEGXJMUBOQLVDV-UHFFFAOYSA-N 0.000 description 3
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
AHVHMOCPOOCNNS-UHFFFAOYSA-N 4-methylimino-1,1-dioxo-1,2,5-thiadiazol-3-amine Chemical compound NC1=NS(N=C1NC)(=O)=O AHVHMOCPOOCNNS-UHFFFAOYSA-N 0.000 description 3
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 3
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229940125715 antihistaminic agent Drugs 0.000 description 3
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238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000012453 solvate Substances 0.000 description 3
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
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OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 2
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239000000969 carrier Substances 0.000 description 2
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229920001277 pectin Polymers 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
229940127293 prostanoid Drugs 0.000 description 1
150000003814 prostanoids Chemical class 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
210000005245 right atrium Anatomy 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000002731 stomach secretion inhibitor Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
LKHDXIBHVSGUHN-UHFFFAOYSA-N thiadiazole 1,1-dioxide Chemical compound O=S1(=O)C=CN=N1 LKHDXIBHVSGUHN-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
229960003223 tripelennamine Drugs 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Plural Heterocyclic Compounds (AREA)

CS813166A 1980-04-30 1981-04-28 Způsob pHpravy 3.4-diamino-1,2,5-thiadiazolových derivátů CS244411B2 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US14516180A	1980-04-30	1980-04-30

Publications (2)

Publication Number	Publication Date
CS316681A2 CS316681A2 (en)	1985-09-17
CS244411B2 true CS244411B2 (cs)	1986-07-17

Family

ID=22511871

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS813166A CS244411B2 (cs)	1980-04-30	1981-04-28	Způsob pHpravy 3.4-diamino-1,2,5-thiadiazolových derivátů

Country Status (3)

Country	Link
JP (1)	JPS579775A (ja)
CS (1)	CS244411B2 (ja)
ZA (1)	ZA812834B (ja)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0065823A1 (en) *	1981-05-13	1982-12-01	Imperial Chemical Industries Plc	Heterocyclic guanidines as histamine H-2 antagonists

1981
- 1981-04-28 CS CS813166A patent/CS244411B2/cs unknown
- 1981-04-29 ZA ZA00812834A patent/ZA812834B/xx unknown
- 1981-04-30 JP JP6431181A patent/JPS579775A/ja active Pending

Also Published As

Publication number	Publication date
ZA812834B (en)	1982-12-29
CS316681A2 (en)	1985-09-17
JPS579775A (en)	1982-01-19

Publication	Publication Date	Title
EP0040696B1 (en)	1986-08-27	Aminothiadiazoles as gastric secretion inhibitors
EP0049618B1 (en)	1985-08-14	Improvements in or relating to 2,4-disubstituted thiazole derivatives
SE416049B (sv)	1980-11-24	Forfarande for framstellning av 1,1-diaminoctylenderivat, som kan anvendas for hemning av vissa histaminverkningar
NL8004967A (nl)	1981-03-06	3,4-digesubstitueerde-1,2,5-thiadiazool-1-oxydan en 1,1-diozyden, alsmede farmaceutische preparaten die deze verbindingen als actieve component bevatten.
HU198042B (en)	1989-07-28	Process for production of derivatives of tiasolidindion and medical preparatives containing these substances
US4524071A (en)	1985-06-18	Pyrimidone derivatives
IE53068B1 (en)	1988-05-25	Diamino isothiazole-1-oxides and -1,1-dioxides as gastic secretion inhibitors
EP0007679A1 (en)	1980-02-06	Oxime ethers, processes for their manufacture and pharmaceutical compositions thereof
KR100199356B1 (ko)	1999-06-15	피리딘유도체, 이의 제조방법 및 용도
US3849423A (en)	1974-11-19	3-benzylpyridines
US3740409A (en)	1973-06-19	2-amino(and 2-aminomethyl)-2-heterocyclic-thioacetamides
US4497810A (en)	1985-02-05	Thiatriazine dioxides as gastric anti-secretory agents
US5294629A (en)	1994-03-15	Benzothiazole and benzimidazole derivatives and antiulcer agent containing the same
EP0073971B1 (en)	1986-05-21	Thiadiazole oxides as gastric antisecretory agents
US3898335A (en)	1975-08-05	Pharmaceutical compositions and methods of inhibiting gastric acid secretion
CS244411B2 (cs)	1986-07-17	Způsob pHpravy 3.4-diamino-1,2,5-thiadiazolových derivátů
US4904792A (en)	1990-02-27	N-thiazolymethylthioalkyl-N'-alkylamidines and related compounds
PL141540B1 (en)	1987-08-31	Process for preparing n-substituted 1-oxide of nicotinic acid amide
US4312869A (en)	1982-01-26	Monosubstituted piperazines
CS197238B2 (en)	1980-04-30	Method of producing novel acylated derivatives of 2-amino thiazole
US4760075A (en)	1988-07-26	N-thiazolylmethylthioalkyl-N-alkyl-amidines and related compounds
US4118567A (en)	1978-10-03	3-Morpholino-2-heterocyclic-thiopropanamides
US4843085A (en)	1989-06-27	Pyridine derivatives, process for production thereof and pharmaceutical compositions useful as anti-arhytmics
KR850000910B1 (ko)	1985-06-27	아미노티아디아졸의 제법
DK163732B (da)	1992-03-30	N-oe2-oeoe5-(aminomethyl)-2-fyranylaamethylthioaa-ethylaa-2-nitro-1,1-ethen-diaminderivater, fremgangsmaade til deres fremstilling og anvendelse af derivaterne til fremstilling af laegemidler