JPS584773A - ピリダジノン誘導体 - Google Patents

Info

Publication number

JPS584773A

JPS584773A JP7712481A JP7712481A JPS584773A JP S584773 A JPS584773 A JP S584773A JP 7712481 A JP7712481 A JP 7712481A JP 7712481 A JP7712481 A JP 7712481A JP S584773 A JPS584773 A JP S584773A

Authority

JP

Japan

Prior art keywords

formula

general formula

derivative

represented

compound

Prior art date

1981-05-20

Legal status (The legal status 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 status listed.)

Granted

Links

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• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 12
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
• 150000001412 amines Chemical class 0.000 claims abstract description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
• 150000002541 isothioureas Chemical class 0.000 claims abstract description 4
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
• -1 amine compound Chemical class 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• 239000011593 sulfur Substances 0.000 claims description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 43
• 239000002904 solvent Substances 0.000 abstract description 18
• 238000000034 method Methods 0.000 abstract description 14
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract description 6
• 238000001816 cooling Methods 0.000 abstract description 5
• 238000010992 reflux Methods 0.000 abstract description 5
• 208000008469 Peptic Ulcer Diseases 0.000 abstract description 4
• 208000011906 peptic ulcer disease Diseases 0.000 abstract description 3
• 239000000463 material Substances 0.000 abstract description 2
• 230000003449 preventive effect Effects 0.000 abstract 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
• 125000003118 aryl group Chemical group 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 17
• 239000013078 crystal Substances 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• 239000000203 mixture Substances 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• 238000002844 melting Methods 0.000 description 9
• 230000008018 melting Effects 0.000 description 9
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
• 238000000862 absorption spectrum Methods 0.000 description 8
• 238000000921 elemental analysis Methods 0.000 description 8
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• 238000001819 mass spectrum Methods 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 239000000843 powder Substances 0.000 description 4
• 101100460385 Caenorhabditis elegans nhx-2 gene Proteins 0.000 description 3
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
• 208000007107 Stomach Ulcer Diseases 0.000 description 3
• 208000025865 Ulcer Diseases 0.000 description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
• 230000000694 effects Effects 0.000 description 3
• 201000005917 gastric ulcer Diseases 0.000 description 3
• CEAJFNBWKBTRQE-UHFFFAOYSA-N methanamine;methanol Chemical compound NC.OC CEAJFNBWKBTRQE-UHFFFAOYSA-N 0.000 description 3
• 231100000397 ulcer Toxicity 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 2
• 208000000718 duodenal ulcer Diseases 0.000 description 2
• 239000012442 inert solvent Substances 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 238000001228 spectrum Methods 0.000 description 2
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
• APLNAFMUEHKRLM-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)N=CN2 APLNAFMUEHKRLM-UHFFFAOYSA-N 0.000 description 1
• 101100460384 Arabidopsis thaliana NHX2 gene Proteins 0.000 description 1
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
• 206010020601 Hyperchlorhydria Diseases 0.000 description 1
• 241000700159 Rattus Species 0.000 description 1
• 101000697856 Rattus norvegicus Bile acid-CoA:amino acid N-acyltransferase Proteins 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 229910052796 boron Inorganic materials 0.000 description 1
• GMEGXJPUFRVCPX-UHFFFAOYSA-N butylthiourea Chemical compound CCCCNC(N)=S GMEGXJPUFRVCPX-UHFFFAOYSA-N 0.000 description 1
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 230000001747 exhibiting effect Effects 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 210000004211 gastric acid Anatomy 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 238000005259 measurement Methods 0.000 description 1
• 239000011259 mixed solution Substances 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 230000028327 secretion Effects 0.000 description 1
• 230000003595 spectral effect Effects 0.000 description 1
• 230000002269 spontaneous effect Effects 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
• 230000002747 voluntary effect Effects 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1