BE539594A - - Google Patents
Info
- Publication number
- BE539594A BE539594A BE539594DA BE539594A BE 539594 A BE539594 A BE 539594A BE 539594D A BE539594D A BE 539594DA BE 539594 A BE539594 A BE 539594A
- Authority
- BE
- Belgium
- Prior art keywords
- bromide
- mol
- mixture
- methyl
- ethanol
- Prior art date
Links
- 239000011780 sodium chloride Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- -1 acyloxyphenyl Chemical group 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 15
- GZUXJHMPEANEGY-UHFFFAOYSA-N Bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 14
- 239000000725 suspension Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- PLHRLQRACPEUSE-UHFFFAOYSA-N pyridine-3-sulfinic acid Chemical compound OS(=O)C1=CC=CN=C1 PLHRLQRACPEUSE-UHFFFAOYSA-N 0.000 description 10
- 239000003039 volatile agent Substances 0.000 description 10
- VKYHIODZAAYFQP-UHFFFAOYSA-N 1-phenyl-2-pyridin-3-ylsulfonylethanone Chemical compound C=1C=CC=CC=1C(=O)CS(=O)(=O)C1=CC=CN=C1 VKYHIODZAAYFQP-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- LYGJENNIWJXYER-UHFFFAOYSA-N Nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229940102396 methyl bromide Drugs 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- VVPKDBSEKFTDKW-UHFFFAOYSA-N 3-pyridin-3-ylsulfonylpyridine Chemical compound C=1C=CN=CC=1S(=O)(=O)C1=CC=CN=C1 VVPKDBSEKFTDKW-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O Pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- QRXWMOHMRWLFEY-UHFFFAOYSA-N Isoniazid Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
- KWCBBNWVHVJHNJ-UHFFFAOYSA-N N1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=C(C=C1)[N+](=O)[O-] Chemical compound N1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=C(C=C1)[N+](=O)[O-] KWCBBNWVHVJHNJ-UHFFFAOYSA-N 0.000 description 2
- IMACFCSSMIZSPP-UHFFFAOYSA-N Phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-Bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- FKJSFKCZZIXQIP-UHFFFAOYSA-N 2-bromo-1-(4-bromophenyl)ethanone Chemical compound BrCC(=O)C1=CC=C(Br)C=C1 FKJSFKCZZIXQIP-UHFFFAOYSA-N 0.000 description 1
- MBUPVGIGAMCMBT-UHFFFAOYSA-N 2-bromo-1-(4-nitrophenyl)ethanone Chemical compound [O-][N+](=O)C1=CC=C(C(=O)CBr)C=C1 MBUPVGIGAMCMBT-UHFFFAOYSA-N 0.000 description 1
- VXZKWVJFIXGRKM-UHFFFAOYSA-N 2-phenacylsulfonyl-1-phenylethanone Chemical class C=1C=CC=CC=1C(=O)CS(=O)(=O)CC(=O)C1=CC=CC=C1 VXZKWVJFIXGRKM-UHFFFAOYSA-N 0.000 description 1
- LJANCPRIUMHGJE-UHFFFAOYSA-N 4-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=C(C#N)C=C1 LJANCPRIUMHGJE-UHFFFAOYSA-N 0.000 description 1
- SMIOEQSLJNNKQF-UHFFFAOYSA-N 4-acetoxy acetophenone Chemical compound CC(=O)OC1=CC=C(C(C)=O)C=C1 SMIOEQSLJNNKQF-UHFFFAOYSA-N 0.000 description 1
- VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 1
- 229940036592 ANTHELMINTICS Drugs 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N Bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- PAIFQYFFDOMKQI-UHFFFAOYSA-N C(C)(=O)OC(C(=O)C1=CC=CC=C1)S(=O)(=O)C(C(=O)C1=CC=CC=C1)OC(C)=O Chemical class C(C)(=O)OC(C(=O)C1=CC=CC=C1)S(=O)(=O)C(C(=O)C1=CC=CC=C1)OC(C)=O PAIFQYFFDOMKQI-UHFFFAOYSA-N 0.000 description 1
- 206010014881 Enterobiasis Diseases 0.000 description 1
- 241000498255 Enterobius vermicularis Species 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N N-Propyl bromide Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- RKZRQFRSFLTDRP-UHFFFAOYSA-N N1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=C(C=C1)OC Chemical compound N1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=C(C=C1)OC RKZRQFRSFLTDRP-UHFFFAOYSA-N 0.000 description 1
- JXLGFVSMRZTYFX-UHFFFAOYSA-N N1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=C(C=C1)OC(C)=O Chemical compound N1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=C(C=C1)OC(C)=O JXLGFVSMRZTYFX-UHFFFAOYSA-N 0.000 description 1
- TVWIIYNEQSLZPQ-UHFFFAOYSA-N NC(C(=O)C1=CC=CC=C1)S(=O)(=O)C(C(=O)C1=CC=CC=C1)N Chemical class NC(C(=O)C1=CC=CC=C1)S(=O)(=O)C(C(=O)C1=CC=CC=C1)N TVWIIYNEQSLZPQ-UHFFFAOYSA-N 0.000 description 1
- NEQOAXVWUKMUTB-UHFFFAOYSA-N OC(C(=O)C1=CC=CC=C1)S(=O)(=O)C(C(=O)C1=CC=CC=C1)O Chemical class OC(C(=O)C1=CC=CC=C1)S(=O)(=O)C(C(=O)C1=CC=CC=C1)O NEQOAXVWUKMUTB-UHFFFAOYSA-N 0.000 description 1
- SPCDJZGDCHUTIM-UHFFFAOYSA-N [4-(2-bromoacetyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=C(C(=O)CBr)C=C1 SPCDJZGDCHUTIM-UHFFFAOYSA-N 0.000 description 1
- WMGUXEAVVMKAFP-UHFFFAOYSA-M [Br-].C(CCC)[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=CC=C1 Chemical compound [Br-].C(CCC)[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=CC=C1 WMGUXEAVVMKAFP-UHFFFAOYSA-M 0.000 description 1
- ZYFWILUTMNJKSU-UHFFFAOYSA-M [Br-].C(CCCC)[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=CC=C1 Chemical compound [Br-].C(CCCC)[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=CC=C1 ZYFWILUTMNJKSU-UHFFFAOYSA-M 0.000 description 1
- GTHCUGHNTLMMFM-UHFFFAOYSA-M [Br-].CCC[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=CC=C1 Chemical compound [Br-].CCC[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=CC=C1 GTHCUGHNTLMMFM-UHFFFAOYSA-M 0.000 description 1
- RBFYWPFZHRWEQC-UHFFFAOYSA-M [Br-].C[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=C(C=C1)OC Chemical compound [Br-].C[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=C(C=C1)OC RBFYWPFZHRWEQC-UHFFFAOYSA-M 0.000 description 1
- FPAKTNFJWIIKFP-UHFFFAOYSA-M [Cl-].C(C(=O)C1=CC=CC=C1)[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=CC=C1 Chemical compound [Cl-].C(C(=O)C1=CC=CC=C1)[N+]1=CC(=CC=C1)S(=O)(=O)CC(=O)C1=CC=CC=C1 FPAKTNFJWIIKFP-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000507 anthelmentic Effects 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000005591 charge neutralization Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 230000000850 deacetylating Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910001509 metal bromide Inorganic materials 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N methoxyethyl Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- DVECLMOWYVDJRM-UHFFFAOYSA-N pyridine-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN=C1 DVECLMOWYVDJRM-UHFFFAOYSA-N 0.000 description 1
- CDRNYKLYADJTMN-UHFFFAOYSA-N pyridine-3-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CN=C1 CDRNYKLYADJTMN-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE539594A true BE539594A (ja) |
Family
ID=169252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE539594D BE539594A (ja) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE539594A (ja) |
-
0
- BE BE539594D patent/BE539594A/fr unknown
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