JPH0560833B2 - - Google Patents

Info

Publication number: JPH0560833B2
Authority: JP; Japan
Prior art keywords: group; compound; acetyl; methoxyphenyl; lower alkyl
Prior art date: 1986-10-23
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.): Expired - Lifetime

Application number

JP61253158A

Other languages

English (en)

Japanese (ja)

Other versions

JPS63104969A (ja

Inventor

Junichi Iwao

Tadashi Iso

Yoichi Kawashima

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Santen Pharmaceutical Co Ltd

Original Assignee

Santen Pharmaceutical Co Ltd

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.)

1986-10-23

Filing date

1986-10-23

Publication date

1993-09-03

1986-10-23 Application filed by Santen Pharmaceutical Co Ltd filed Critical Santen Pharmaceutical Co Ltd

1986-10-23 Priority to JP61253158A priority Critical patent/JPS63104969A/ja

1988-05-10 Publication of JPS63104969A publication Critical patent/JPS63104969A/ja

1993-09-03 Publication of JPH0560833B2 publication Critical patent/JPH0560833B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 69
125000000217 alkyl group Chemical group 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000002071 phenylalkoxy group Chemical group 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 3
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 80
-1 phenyloxy group Chemical group 0.000 description 30
238000002844 melting Methods 0.000 description 25
230000008018 melting Effects 0.000 description 25
239000000243 solution Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
238000000034 method Methods 0.000 description 8
238000010898 silica gel chromatography Methods 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
FBOSKQVOIHEWAX-UHFFFAOYSA-N benzothiazine Chemical compound C1=CC=C2N=CCSC2=C1 FBOSKQVOIHEWAX-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
ROSJMNJJOXFJGH-UHFFFAOYSA-N 1-[2-(2-hydroxy-5-methoxyphenyl)-2h-1,3-benzothiazol-3-yl]ethanone Chemical compound COC1=CC=C(O)C(C2N(C3=CC=CC=C3S2)C(C)=O)=C1 ROSJMNJJOXFJGH-UHFFFAOYSA-N 0.000 description 6
WOHLSTOWRAOMSG-UHFFFAOYSA-N 2,3-dihydro-1,3-benzothiazole Chemical compound C1=CC=C2SCNC2=C1 WOHLSTOWRAOMSG-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000013078 crystal Substances 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
125000005530 alkylenedioxy group Chemical group 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
OSIHAUUUEFEAKY-UHFFFAOYSA-N 2-(2-hydroxy-5-methoxyphenyl)-4-methyl-1,4-benzothiazin-3-one Chemical compound COC1=CC=C(O)C(C2C(N(C)C3=CC=CC=C3S2)=O)=C1 OSIHAUUUEFEAKY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
OTXANOLOOUNVSR-UHFFFAOYSA-N N-Methylmescaline Chemical compound CNCCC1=CC(OC)=C(OC)C(OC)=C1 OTXANOLOOUNVSR-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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 class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
PCVMCOHQOWNKRL-SQBRYUAOSA-N [2-(3-acetyl-2h-1,3-benzothiazol-2-yl)-4-methoxyphenyl] (2r,4r)-3-acetyl-2-phenyl-1,3-thiazolidine-4-carboxylate Chemical compound C1([C@H]2SC[C@H](N2C(C)=O)C(=O)OC2=CC=C(C=C2C2N(C3=CC=CC=C3S2)C(C)=O)OC)=CC=CC=C1 PCVMCOHQOWNKRL-SQBRYUAOSA-N 0.000 description 2
XLUXHEZIGIDTCC-UHFFFAOYSA-N acetonitrile;ethyl acetate Chemical compound CC#N.CCOC(C)=O XLUXHEZIGIDTCC-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
SYWUAPJQKHSVPQ-UHFFFAOYSA-N benzene;ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O.C1=CC=CC=C1 SYWUAPJQKHSVPQ-UHFFFAOYSA-N 0.000 description 2
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
230000002213 calciumantagonistic effect Effects 0.000 description 2
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
JXGVXCZADZNAMJ-NSHDSACASA-N (2s)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)OCC1=CC=CC=C1 JXGVXCZADZNAMJ-NSHDSACASA-N 0.000 description 1
SRUYMBLDQDAWJX-UHFFFAOYSA-N 1,4-benzothiazin-2-one Chemical compound C1=CC=C2SC(=O)C=NC2=C1 SRUYMBLDQDAWJX-UHFFFAOYSA-N 0.000 description 1
BXXWFOGWXLJPPA-UHFFFAOYSA-N 2,3-dibromobutane Chemical compound CC(Br)C(C)Br BXXWFOGWXLJPPA-UHFFFAOYSA-N 0.000 description 1
PQDZYOUYROPJGN-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)-n-methylethanamine Chemical compound CNCCOC1=CC=C2OCOC2=C1 PQDZYOUYROPJGN-UHFFFAOYSA-N 0.000 description 1
AWIQPVLXRJFXQU-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-4-methoxyphenol Chemical compound COC1=CC=C(O)C(C=2SC3=CC=CC=C3N=2)=C1 AWIQPVLXRJFXQU-UHFFFAOYSA-N 0.000 description 1
DIEJEELGDWGUCV-WLHGVMLRSA-N 2-[2-[3-[2-(1,3-benzodioxol-5-yloxy)ethyl-methylamino]propoxy]-5-methoxyphenyl]-4-methyl-1,4-benzothiazin-3-one;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.S1C2=CC=CC=C2N(C)C(=O)C1C1=CC(OC)=CC=C1OCCCN(C)CCOC1=CC=C(OCO2)C2=C1 DIEJEELGDWGUCV-WLHGVMLRSA-N 0.000 description 1
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
ZULJYVVAYGFYKU-UHFFFAOYSA-N acetonitrile;chloroform Chemical compound CC#N.ClC(Cl)Cl ZULJYVVAYGFYKU-UHFFFAOYSA-N 0.000 description 1
AUALQMFGWLZREY-UHFFFAOYSA-N acetonitrile;methanol Chemical compound OC.CC#N AUALQMFGWLZREY-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
AMZONRRFUQKTSZ-UHFFFAOYSA-N benzene;2-propan-2-yloxypropane Chemical compound C1=CC=CC=C1.CC(C)OC(C)C AMZONRRFUQKTSZ-UHFFFAOYSA-N 0.000 description 1
229960004217 benzyl alcohol Drugs 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
208000015606 cardiovascular system disease Diseases 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000010575 fractional recrystallization Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
PFPYHYZFFJJQFD-UHFFFAOYSA-N oxalic anhydride Chemical compound O=C1OC1=O PFPYHYZFFJJQFD-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
ULSZVNJBVJWEJE-UHFFFAOYSA-N thiazolidine-2-carboxylic acid Chemical compound OC(=O)C1NCCS1 ULSZVNJBVJWEJE-UHFFFAOYSA-N 0.000 description 1
DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 1
229950001139 timonacic Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Thiazole And Isothizaole Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Plural Heterocyclic Compounds (AREA)

JP61253158A 1986-10-23 1986-10-23 含硫黄複素環化合物 Granted JPS63104969A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP61253158A JPS63104969A (ja)	1986-10-23	1986-10-23	含硫黄複素環化合物

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP61253158A JPS63104969A (ja)	1986-10-23	1986-10-23	含硫黄複素環化合物

Publications (2)

Publication Number	Publication Date
JPS63104969A JPS63104969A (ja)	1988-05-10
JPH0560833B2 true JPH0560833B2 (fi)	1993-09-03

Family

ID=17247337

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61253158A Granted JPS63104969A (ja)	1986-10-23	1986-10-23	含硫黄複素環化合物

Country Status (1)

Country	Link
JP (1)	JPS63104969A (fi)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69028603T2 (de) *	1989-06-16	1997-02-13	Santen Pharmaceutical Co Ltd	Arzneimittel für bessere gehirnwirkung
US6673815B2 (en) *	2001-11-06	2004-01-06	Bristol-Myers Squibb Company	Substituted acid derivatives useful as antidiabetic and antiobesity agents and method

1986
- 1986-10-23 JP JP61253158A patent/JPS63104969A/ja active Granted

Also Published As

Publication number	Publication date
JPS63104969A (ja)	1988-05-10

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