SK100096A3 - 1,3-benzodioxole-5-ylacetic acid derivative, preparing process thereof and pharmaceutical composition containing them - Google Patents

1,3-benzodioxole-5-ylacetic acid derivative, preparing process thereof and pharmaceutical composition containing them Download PDF

Info

Publication number: SK100096A3
Authority: SK; Slovakia
Prior art keywords: benzodioxol; group; formula; dihydro; atoms
Prior art date: 1995-08-16

Application number

SK1000-96A

Other languages

English (en)

Slovak (sk)

Inventor

Dieter Dr Dorsch

Mathias Dr Oswald

Werner Dr Mederski

Claudia Dr Wilm

Claus Dr Schmitges

Maria Christadler

Original Assignee

Merck Patent Gmbh

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.)

1995-08-16

Filing date

1996-07-31

Publication date

1997-03-05

1996-07-31 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1997-03-05 Publication of SK100096A3 publication Critical patent/SK100096A3/sk

Links

ODVLMCWNGKLROU-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)acetic acid Chemical class OC(=O)CC1=CC=C2OCOC2=C1 ODVLMCWNGKLROU-UHFFFAOYSA-N 0.000 title claims description 12
239000008194 pharmaceutical composition Substances 0.000 title claims description 12
238000000034 method Methods 0.000 title claims description 10
-1 1H-tetrazol-5-yl Chemical group 0.000 claims abstract description 212
150000003839 salts Chemical class 0.000 claims abstract description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
125000002947 alkylene group Chemical group 0.000 claims abstract description 8
125000001624 naphthyl group Chemical group 0.000 claims abstract description 8
229910052740 iodine Inorganic materials 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
229910052794 bromium Inorganic materials 0.000 claims abstract description 6
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 39
238000011282 treatment Methods 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 10
125000003277 amino group Chemical group 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004185 ester group Chemical group 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
238000006268 reductive amination reaction Methods 0.000 claims description 3
JCOCJLFUXDDTAT-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-2-(1,3-dioxoisoindol-5-yl)oxyacetic acid Chemical compound C1=C2OCOC2=CC(C(OC=2C=C3C(=O)NC(=O)C3=CC=2)C(=O)O)=C1 JCOCJLFUXDDTAT-UHFFFAOYSA-N 0.000 claims description 2
XOMOCLJYOAAIRD-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-n-(4-tert-butylphenyl)sulfonyl-2-(1,3-dioxoisoindol-5-yl)oxyacetamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC(=O)C(C=1C=C2OCOC2=CC=1)OC1=CC=C(C(=O)NC2=O)C2=C1 XOMOCLJYOAAIRD-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
239000002552 dosage form Substances 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
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 claims description 2
JXAIAVVSWQCFFX-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-2-(1-methyl-2-propylbenzimidazol-4-yl)oxyacetic acid Chemical compound C1=C2OCOC2=CC(C(C(O)=O)OC2=C3N=C(N(C3=CC=C2)C)CCC)=C1 JXAIAVVSWQCFFX-UHFFFAOYSA-N 0.000 claims 1
PHESBRDFBLEIRT-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-2-(7-propylquinolin-8-yl)oxyacetic acid Chemical compound C1=C2OCOC2=CC(C(C(O)=O)OC2=C3N=CC=CC3=CC=C2CCC)=C1 PHESBRDFBLEIRT-UHFFFAOYSA-N 0.000 claims 1
CGMZJSADDCSVFZ-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-2-[(6-propyl-1h-indol-7-yl)oxy]acetic acid Chemical compound C1=C2OCOC2=CC(C(C(O)=O)OC2=C3NC=CC3=CC=C2CCC)=C1 CGMZJSADDCSVFZ-UHFFFAOYSA-N 0.000 claims 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
229940118365 Endothelin receptor antagonist Drugs 0.000 claims 1
150000001450 anions Chemical class 0.000 claims 1
239000002308 endothelin receptor antagonist Substances 0.000 claims 1
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 abstract 3
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 abstract 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 abstract 1
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 abstract 1
229910052717 sulfur Inorganic materials 0.000 abstract 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 13
238000010265 fast atom bombardment Methods 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
102000002045 Endothelin Human genes 0.000 description 6
108050009340 Endothelin Proteins 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
235000011054 acetic acid Nutrition 0.000 description 6
ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 description 6
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
206010019280 Heart failures Diseases 0.000 description 5
206010020772 Hypertension Diseases 0.000 description 5
239000002585 base Substances 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 4
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 4
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
KYDZEZNYRFJCSA-UHFFFAOYSA-N 4-tert-butylbenzenesulfonamide Chemical compound CC(C)(C)C1=CC=C(S(N)(=O)=O)C=C1 KYDZEZNYRFJCSA-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
102000010180 Endothelin receptor Human genes 0.000 description 3
108050001739 Endothelin receptor Proteins 0.000 description 3
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 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001243 acetic acids Chemical class 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
230000003042 antagnostic effect Effects 0.000 description 3
230000017531 blood circulation Effects 0.000 description 3
210000004204 blood vessel Anatomy 0.000 description 3
239000012154 double-distilled water Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000011321 prophylaxis Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229940033134 talc Drugs 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
IZFOPMSVNDORMZ-UHFFFAOYSA-N 1-benzofuran-5-ol Chemical compound OC1=CC=C2OC=CC2=C1 IZFOPMSVNDORMZ-UHFFFAOYSA-N 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
NHXFINXXELODNV-UHFFFAOYSA-N 5-hydroxyisoindole-1,3-dione Chemical compound OC1=CC=C2C(=O)NC(=O)C2=C1 NHXFINXXELODNV-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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239000007868 Raney catalyst Substances 0.000 description 2
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PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
239000007924 injection Substances 0.000 description 2
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239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
NPKATACLAVJRPB-UHFFFAOYSA-N methyl 2-(1,3-benzodioxol-5-yl)-2-bromoacetate Chemical compound COC(=O)C(Br)C1=CC=C2OCOC2=C1 NPKATACLAVJRPB-UHFFFAOYSA-N 0.000 description 2
KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical class COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
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235000011007 phosphoric acid Nutrition 0.000 description 2
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BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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239000007858 starting material Substances 0.000 description 2
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pulmonology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

SK1000-96A 1995-08-16 1996-07-31 1,3-benzodioxole-5-ylacetic acid derivative, preparing process thereof and pharmaceutical composition containing them SK100096A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19530032A DE19530032A1 (de)	1995-08-16	1995-08-16	Endothelin-Rezeptor-Antagonisten

Publications (1)

Publication Number	Publication Date
SK100096A3 true SK100096A3 (en)	1997-03-05

Family

ID=7769557

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1000-96A SK100096A3 (en)	1995-08-16	1996-07-31	1,3-benzodioxole-5-ylacetic acid derivative, preparing process thereof and pharmaceutical composition containing them

Country Status (17)

Country	Link
US (1)	US5821256A (ja)
EP (1)	EP0758650A1 (ja)
JP (1)	JPH0959273A (ja)
KR (1)	KR970010756A (ja)
CN (1)	CN1149583A (ja)
AR (1)	AR003286A1 (ja)
AU (1)	AU6200296A (ja)
BR (1)	BR9603432A (ja)
CA (1)	CA2183307A1 (ja)
CZ (1)	CZ240096A3 (ja)
DE (1)	DE19530032A1 (ja)
HU (1)	HUP9602253A3 (ja)
MX (1)	MX9603343A (ja)
NO (1)	NO963411L (ja)
PL (1)	PL315707A1 (ja)
SK (1)	SK100096A3 (ja)
ZA (1)	ZA966933B (ja)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9602029D0 (en) *	1996-02-01	1996-04-03	Fujisawa Pharmaceutical Co	New heterocyclic compounds
DE19710831A1 (de) *	1997-03-15	1998-09-17	Merck Patent Gmbh	Endothelin-Rezeptor-Antagonisten
EP1366012A4 (en) *	2001-02-09	2005-11-02	Merck & Co Inc	2-ARYLOXY-2-ARYLALKANIC ACIDS AGAINST DIABETES AND FAILURE CHANGES
DE10155076A1 (de) *	2001-11-09	2003-05-22	Merck Patent Gmbh	Verwendung von Endothelin-Rezeptor-Antagonisten zur Behandlung von Tumorerkrankungen
EP1926989A4 (en) *	2005-08-12	2008-12-24	Uop Llc	METHOD AND DEVICE FOR ACCELERATING SAMPLE ANALYSIS

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH07110833B2 (ja) *	1986-12-02	1995-11-29	株式会社トクヤマ	α−置換フエニル酢酸誘導体
RU2086544C1 (ru) *	1991-06-13	1997-08-10	Хоффманн-Ля Рош АГ	Бензолсульфонамидные производные пиримидина или их соли, фармацевтическая композиция для лечения заболеваний, связанных с активностью эндотелина
GB9115153D0 (en) *	1991-07-12	1991-08-28	Patel Bipin C M	Sol-gel composition for producing glassy coatings
FI942059L (fi) *	1991-11-05	1994-07-04	Smithkline Beecham Corp	Endoteliinireseptoreiden antagonisteja
ZA939516B (en) *	1992-12-22	1994-06-06	Smithkline Beecham Corp	Endothelin receptor antagonists
ES2141197T3 (es) *	1993-03-19	2000-03-16	Merck & Co Inc	Derivados del acido fenoxifenilacetico.
WO1996009818A1 (en) *	1994-09-27	1996-04-04	Merck & Co., Inc.	Endothelin receptor antagonists for the treatment of emesis

1995
- 1995-08-16 DE DE19530032A patent/DE19530032A1/de not_active Withdrawn
1996
- 1996-07-31 SK SK1000-96A patent/SK100096A3/sk unknown
- 1996-08-06 EP EP96112667A patent/EP0758650A1/de not_active Withdrawn
- 1996-08-09 AU AU62002/96A patent/AU6200296A/en not_active Abandoned
- 1996-08-13 MX MX9603343A patent/MX9603343A/es unknown
- 1996-08-14 PL PL96315707A patent/PL315707A1/xx unknown
- 1996-08-14 CN CN96111668A patent/CN1149583A/zh active Pending
- 1996-08-14 CZ CZ962400A patent/CZ240096A3/cs unknown
- 1996-08-14 CA CA002183307A patent/CA2183307A1/en not_active Abandoned
- 1996-08-14 KR KR1019960033775A patent/KR970010756A/ko not_active Withdrawn
- 1996-08-15 ZA ZA9606933A patent/ZA966933B/xx unknown
- 1996-08-15 US US08/698,331 patent/US5821256A/en not_active Expired - Fee Related
- 1996-08-15 HU HU9602253A patent/HUP9602253A3/hu unknown
- 1996-08-15 NO NO963411A patent/NO963411L/no unknown
- 1996-08-15 BR BR9603432A patent/BR9603432A/pt not_active Application Discontinuation
- 1996-08-16 AR ARP960104020A patent/AR003286A1/es unknown
- 1996-08-16 JP JP8233711A patent/JPH0959273A/ja active Pending

Also Published As

Publication number	Publication date
PL315707A1 (en)	1997-02-17
HUP9602253A2 (en)	1997-12-29
NO963411L (no)	1997-02-17
KR970010756A (ko)	1997-03-27
HUP9602253A3 (en)	1999-06-28
CA2183307A1 (en)	1997-02-17
EP0758650A1 (de)	1997-02-19
AR003286A1 (es)	1998-07-08
AU6200296A (en)	1997-02-20
BR9603432A (pt)	1998-05-12
JPH0959273A (ja)	1997-03-04
NO963411D0 (no)	1996-08-15
CZ240096A3 (en)	1997-03-12
CN1149583A (zh)	1997-05-14
MX9603343A (es)	1997-03-29
US5821256A (en)	1998-10-13
ZA966933B (en)	1997-02-19
HU9602253D0 (en)	1996-10-28
DE19530032A1 (de)	1997-02-20

Publication	Publication Date	Title
RU2168503C2 (ru)	2001-06-10	Производные сульфонамидов, способ их получения и фармацевтическая композиция
CZ291851B6 (cs)	2003-06-18	Derivát arylalkanoylpyridazinu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje
SK110096A3 (en)	1997-08-06	Arylalkyldiazinon derivative, preparation method thereof and pharmaceutical composition containing same
HU190408B (en)	1986-09-29	Process for producing pharmaceutical preparations comprising new benzimidazole-derivatives
DE19543639A1 (de)	1997-05-28	Endothelin-Rezeptor-Antagonisten
CZ298805B6 (cs)	2008-02-06	Derivát arylalkanoylpyridazinu, zpusob jeho prípravy a farmaceutický prostredek, který ho obsahuje
CZ20011551A3 (cs)	2001-08-15	Derivát benzoylpyridazinu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje
CZ286635B6 (cs)	2000-05-17	Derivát arylalkylthiadiazinonu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje
SK73597A3 (en)	1998-05-06	Pyridazinones as endothelin-receptor antagonists
SK100296A3 (en)	1997-03-05	Oxoquinoline carboxylic acid derivative, preparation method therof and pharmaceutical composition containing its
US5821256A (en)	1998-10-13	Endothelin receptor antagonists
US4482559A (en)	1984-11-13	4-Phenyl-4,5,6,7-tetrahydro-thieno [2,3-c]pyridines, compositions and use
ES2248230T3 (es)	2006-03-16	Piperazinilcarbonil-quinolinas e isoquinolinas.
DE19607096A1 (de)	1997-08-28	Endothelin-Rezeptor-Antagonisten
SK512000A3 (en)	2000-07-11	Benzothia(oxa)diazol derivatives and their use as endothelin-receptor antagonists
SK2652001A3 (en)	2001-09-11	2-oxo-i(2h)-quinoline derivatives
MXPA97004262A (es)	1998-07-03	Piridazinonas como antagonistas del receptor endotelial