CA2095174A1 - Phenyl sulfonamide endothelin antagonists - Google Patents
Phenyl sulfonamide endothelin antagonistsInfo
- Publication number
- CA2095174A1 CA2095174A1 CA002095174A CA2095174A CA2095174A1 CA 2095174 A1 CA2095174 A1 CA 2095174A1 CA 002095174 A CA002095174 A CA 002095174A CA 2095174 A CA2095174 A CA 2095174A CA 2095174 A1 CA2095174 A1 CA 2095174A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- dimethyl
- isoxazolyl
- alkyl
- sulfonamide
- Prior art date
- 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.)
- Abandoned
Links
- 102000002045 Endothelin Human genes 0.000 title claims abstract description 9
- 108050009340 Endothelin Proteins 0.000 title claims abstract description 9
- 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 title claims abstract description 9
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 239000005557 antagonist Substances 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 119
- -1 cycloalkenylalkyl Chemical group 0.000 claims abstract description 81
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 56
- 125000003118 aryl group Chemical group 0.000 claims abstract description 49
- 239000001257 hydrogen Substances 0.000 claims abstract description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 37
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 32
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 31
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 28
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 25
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 55
- 229940124530 sulfonamide Drugs 0.000 claims description 35
- 235000010290 biphenyl Nutrition 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000004450 alkenylene group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 206010020772 Hypertension Diseases 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 208000037487 Endotoxemia Diseases 0.000 claims description 5
- 125000004419 alkynylene group Chemical group 0.000 claims description 5
- 230000001434 glomerular Effects 0.000 claims description 5
- 210000003584 mesangial cell Anatomy 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- FICDMFJBLNFMAR-UHFFFAOYSA-N 2-bromo-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)Br)=C1C FICDMFJBLNFMAR-UHFFFAOYSA-N 0.000 claims description 2
- SBXDENYROQKXBE-UHFFFAOYSA-N 2-phenylbenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 SBXDENYROQKXBE-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 210000003904 glomerular cell Anatomy 0.000 claims 4
- 208000028867 ischemia Diseases 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 2
- GDARDKVQKGHHRI-UHFFFAOYSA-N 2-(2-aminophenyl)-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C(=CC=CC=2)N)=C1C GDARDKVQKGHHRI-UHFFFAOYSA-N 0.000 claims 1
- JNMBQUUVMUDBGI-UHFFFAOYSA-N 2-(3-aminophenyl)-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C=C(N)C=CC=2)=C1C JNMBQUUVMUDBGI-UHFFFAOYSA-N 0.000 claims 1
- XIOWPJCHSRNYQG-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C=CC(=CC=2)C(C)(C)C)=C1C XIOWPJCHSRNYQG-UHFFFAOYSA-N 0.000 claims 1
- FAJJTSBWHDOEGD-UHFFFAOYSA-N 2-(dimethylamino)-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound CN(C)C1=CC=CC=C1S(=O)(=O)NC1=C(C)C(C)=NO1 FAJJTSBWHDOEGD-UHFFFAOYSA-N 0.000 claims 1
- DHAHVLSQWCHUOO-UHFFFAOYSA-N 2-[2-(dimethylamino)phenyl]-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound CN(C)C1=CC=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=C(C)C(C)=NO1 DHAHVLSQWCHUOO-UHFFFAOYSA-N 0.000 claims 1
- IRGOLZQDQJNOFK-UHFFFAOYSA-N 2-[3-(dimethylamino)phenyl]-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound CN(C)C1=CC=CC(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)=C1 IRGOLZQDQJNOFK-UHFFFAOYSA-N 0.000 claims 1
- WXBXZJWIPDOUMI-UHFFFAOYSA-N 2-amino-n-(3,4-dimethyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)N)=C1C WXBXZJWIPDOUMI-UHFFFAOYSA-N 0.000 claims 1
- SQRCNKWHGRNUAM-UHFFFAOYSA-N 2-chloro-n-(3,4-dimethyl-1,2-oxazol-5-yl)-6-methylbenzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2C)Cl)=C1C SQRCNKWHGRNUAM-UHFFFAOYSA-N 0.000 claims 1
- UXGOVZWJTNZGPA-UHFFFAOYSA-N 5-amino-n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-methylbenzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=C(N)C=2)C)=C1C UXGOVZWJTNZGPA-UHFFFAOYSA-N 0.000 claims 1
- DQSKHKMRDFKADZ-UHFFFAOYSA-N 5-butyl-n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-phenylbenzenesulfonamide Chemical compound O1N=C(C)C(C)=C1NS(=O)(=O)C1=CC(CCCC)=CC=C1C1=CC=CC=C1 DQSKHKMRDFKADZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- JKGIOCXEAJIYNE-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-(2-nitrophenyl)benzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C(=CC=CC=2)[N+]([O-])=O)=C1C JKGIOCXEAJIYNE-UHFFFAOYSA-N 0.000 claims 1
- IRWKUXXPQOGSND-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=C(C)C(C)=NO1 IRWKUXXPQOGSND-UHFFFAOYSA-N 0.000 claims 1
- KOIOXZPPAMBEIL-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-(4-methylphenyl)benzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C=CC(C)=CC=2)=C1C KOIOXZPPAMBEIL-UHFFFAOYSA-N 0.000 claims 1
- ZYLOLYHYEVOCLC-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-(4-phenylmethoxyphenyl)benzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=C1C ZYLOLYHYEVOCLC-UHFFFAOYSA-N 0.000 claims 1
- DYLKKVMDOFKPBE-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-(4-propan-2-yloxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC(C)C)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=C(C)C(C)=NO1 DYLKKVMDOFKPBE-UHFFFAOYSA-N 0.000 claims 1
- PTGBBGYJNDIZFK-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-(4-propylphenyl)benzenesulfonamide Chemical compound C1=CC(CCC)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=C(C)C(C)=NO1 PTGBBGYJNDIZFK-UHFFFAOYSA-N 0.000 claims 1
- LMIVZHGYWWZPOD-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-[4-(2-methylpropoxy)phenyl]benzenesulfonamide Chemical compound C1=CC(OCC(C)C)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=C(C)C(C)=NO1 LMIVZHGYWWZPOD-UHFFFAOYSA-N 0.000 claims 1
- BWTQPWDURQZRKQ-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-[4-(2-methylpropyl)phenyl]benzenesulfonamide Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC=CC=C1S(=O)(=O)NC1=C(C)C(C)=NO1 BWTQPWDURQZRKQ-UHFFFAOYSA-N 0.000 claims 1
- ZQUFTQSIAVTDPF-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-naphthalen-1-ylbenzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)=C1C ZQUFTQSIAVTDPF-UHFFFAOYSA-N 0.000 claims 1
- XANLXADXCDHWKP-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-phenoxybenzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)OC=2C=CC=CC=2)=C1C XANLXADXCDHWKP-UHFFFAOYSA-N 0.000 claims 1
- SLBYWDJLJLBXGV-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-phenylbenzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)=C1C SLBYWDJLJLBXGV-UHFFFAOYSA-N 0.000 claims 1
- CWRJTQCWQJJTPF-UHFFFAOYSA-N n-(3,4-dimethyl-1,2-oxazol-5-yl)-2-propan-2-ylbenzenesulfonamide Chemical compound CC(C)C1=CC=CC=C1S(=O)(=O)NC1=C(C)C(C)=NO1 CWRJTQCWQJJTPF-UHFFFAOYSA-N 0.000 claims 1
- ANCMRDKQGAORLD-UHFFFAOYSA-N n-[3-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]-4-methylphenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C)C(S(=O)(=O)NC2=C(C(C)=NO2)C)=C1 ANCMRDKQGAORLD-UHFFFAOYSA-N 0.000 claims 1
- APFKWATYQZKXFJ-UHFFFAOYSA-N n-[3-[2-[(3,4-dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C(=CC=CC=2)S(=O)(=O)NC2=C(C(C)=NO2)C)=C1 APFKWATYQZKXFJ-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 213
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 166
- 229940126062 Compound A Drugs 0.000 description 111
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 111
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 102
- 239000000243 solution Substances 0.000 description 93
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- 239000007787 solid Substances 0.000 description 67
- 229910001868 water Inorganic materials 0.000 description 65
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 44
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- 238000011282 treatment Methods 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 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
- 229960001288 triamterene Drugs 0.000 description 1
- LMJSLTNSBFUCMU-UHFFFAOYSA-N trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 description 1
- 229960004813 trichlormethiazide Drugs 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 description 1
- 229960002769 zofenopril Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/14—Nitrogen atoms
- C07D261/16—Benzene-sulfonamido isoxazoles
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87900092A | 1992-05-06 | 1992-05-06 | |
| US879,000 | 1992-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2095174A1 true CA2095174A1 (en) | 1993-11-07 |
Family
ID=25373236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002095174A Abandoned CA2095174A1 (en) | 1992-05-06 | 1993-04-29 | Phenyl sulfonamide endothelin antagonists |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0569193B1 (enExample) |
| JP (1) | JP3286391B2 (enExample) |
| KR (1) | KR100277454B1 (enExample) |
| CN (1) | CN1066441C (enExample) |
| AT (1) | ATE149155T1 (enExample) |
| AU (1) | AU659545B2 (enExample) |
| CA (1) | CA2095174A1 (enExample) |
| CY (1) | CY2016A (enExample) |
| DE (1) | DE69308229T2 (enExample) |
| DK (1) | DK0569193T3 (enExample) |
| ES (1) | ES2100459T3 (enExample) |
| FI (1) | FI112655B (enExample) |
| GR (1) | GR3023421T3 (enExample) |
| HK (1) | HK98197A (enExample) |
| HU (1) | HU218938B (enExample) |
| IL (1) | IL105481A (enExample) |
| MX (1) | MX9302618A (enExample) |
| NO (1) | NO303065B1 (enExample) |
| NZ (1) | NZ247440A (enExample) |
| PL (1) | PL178165B1 (enExample) |
| RU (1) | RU2133742C1 (enExample) |
| ZA (1) | ZA932914B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5726194A (en) * | 1995-03-18 | 1998-03-10 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Endothelin receptor antagonists |
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| US6124343A (en) * | 1919-01-27 | 2000-09-26 | Rhone-Poulenc Rorer Limited | Substituted phenyl compounds with a substituent having a thienyl ring |
| WO1988005799A1 (fr) * | 1987-02-09 | 1988-08-11 | Mitsui Petrochemical Industries, Ltd. | Materiau de moulage en feuilles et stratifie pour moulages contenant une couche composee dudit materiau |
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| US5962490A (en) | 1987-09-25 | 1999-10-05 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US5591761A (en) * | 1993-05-20 | 1997-01-07 | Texas Biotechnology Corporation | Thiophenyl-, furyl-and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US5571821A (en) * | 1993-05-20 | 1996-11-05 | Texas Biotechnology Corporation | Sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US5594021A (en) * | 1993-05-20 | 1997-01-14 | Texas Biotechnology Corporation | Thienyl-, furyl- and pyrrolyl sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US5736509A (en) * | 1990-12-14 | 1998-04-07 | Texas Biotechnology Corporation | Cyclic peptide surface feature mimics of endothelin |
| US5767310A (en) * | 1993-03-19 | 1998-06-16 | Merck & Co., Inc. | Phenoxyphenylacetic acid derivatives |
| CA2121724A1 (en) | 1993-04-21 | 1994-10-22 | Toshifumi Watanabe | Methods and compositions for the prophylactic and/or therapeutic treatment of organ hypofunction |
| US6342610B2 (en) | 1993-05-20 | 2002-01-29 | Texas Biotechnology Corp. | N-aryl thienyl-, furyl-, and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
| US6030991A (en) * | 1993-05-20 | 2000-02-29 | Texas Biotechnology Corp. | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| US6376523B1 (en) | 1994-05-20 | 2002-04-23 | Texas Biotechnology Corporation | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| US6613804B2 (en) | 1993-05-20 | 2003-09-02 | Encysive Pharmaceuticals, Inc. | Biphenylsulfonamides and derivatives thereof that modulate the activity of endothelin |
| US6541498B2 (en) | 1993-05-20 | 2003-04-01 | Texas Biotechnology | Benzenesulfonamides and the use thereof to modulate the activity of endothelin |
| US5686478A (en) * | 1993-07-20 | 1997-11-11 | Merck & Co. Inc. | Endothelin antagonists |
| ES2081250B1 (es) * | 1993-07-28 | 1996-10-16 | Squibb & Sons Inc | Antagonistas de endotelina a base de fenilsulfonamida. |
| US5965732A (en) * | 1993-08-30 | 1999-10-12 | Bristol-Myers Squibb Co. | Sulfonamide endothelin antagonists |
| JPH09504302A (ja) * | 1993-11-01 | 1997-04-28 | 日本チバガイギー株式会社 | エンドセリン・レセプター・アンタゴニスト |
| US5431842A (en) * | 1993-11-05 | 1995-07-11 | The Procter & Gamble Company | Liquid detergents with ortho-substituted phenylboronic acids for inhibition of proteolytic enzyme |
| IL111959A (en) * | 1993-12-17 | 2000-07-16 | Tanabe Seiyaku Co | N-(polysubstituted pyrimidin-4-yl) benzenesulfonamide derivatives their preparation and pharmaceutical compositions containing them |
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| GB9409618D0 (en) * | 1994-05-13 | 1994-07-06 | Zeneca Ltd | Pyridine derivatives |
| US5612359A (en) * | 1994-08-26 | 1997-03-18 | Bristol-Myers Squibb Company | Substituted biphenyl isoxazole sulfonamides |
| US5538991A (en) * | 1994-09-14 | 1996-07-23 | Merck & Co., Inc. | Endothelin antagonists bearing 5-membered heterocyclic amides |
| US5559135A (en) * | 1994-09-14 | 1996-09-24 | Merck & Co., Inc. | Endothelin antagonists bearing pyridyl amides |
| FR2724654B1 (fr) * | 1994-09-16 | 1997-12-12 | Roussel Uclaf | Nouveaux derives de l'acide gallique, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant |
| FR2725988B1 (fr) * | 1994-10-24 | 1997-01-24 | Roussel Uclaf | Nouveaux derives de pyrazolones et pyrazoles acides, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant |
| US5962682A (en) * | 1994-12-20 | 1999-10-05 | Hoffmann-La Roche Inc. | Aryl- and hetaryl-sulfonamide derivatives, their preparation and their use as endothelin antagonists |
| IL116916A (en) * | 1995-02-06 | 2000-09-28 | Bristol Myers Squibb Co | Substituted biphenyl sulfonamide derivatives and pharmaceutical compositions containing the same |
| US5760038A (en) * | 1995-02-06 | 1998-06-02 | Bristol-Myers Squibb Company | Substituted biphenyl sulfonamide endothelin antagonists |
| NZ306734A (enExample) * | 1995-04-04 | 2000-01-28 | Texas Biotechnology Corp | |
| US5739333A (en) * | 1995-05-16 | 1998-04-14 | Tanabe Seiyaku Co., Ltd. | Sulfonamide derivative and process for preparing the same |
| UA58494C2 (uk) | 1995-06-07 | 2003-08-15 | Зенека Лімітед | Похідні n-гетероарилпіридинсульфонаміду, фармацевтична композиція, спосіб одержання та спосіб протидії впливам ендотеліну |
| GB9512697D0 (en) * | 1995-06-22 | 1995-08-23 | Zeneca Ltd | Heterocyclic compounds |
| US5846990A (en) * | 1995-07-24 | 1998-12-08 | Bristol-Myers Squibb Co. | Substituted biphenyl isoxazole sulfonamides |
| WO1997011942A1 (en) * | 1995-09-26 | 1997-04-03 | Shionogi & Co., Ltd. | Novel sulfonamide compounds and medicinal composition |
| JPH09124620A (ja) * | 1995-10-11 | 1997-05-13 | Bristol Myers Squibb Co | 置換ビフェニルスルホンアミドエンドセリン拮抗剤 |
| DE19540737A1 (de) * | 1995-11-02 | 1997-05-07 | Bayer Ag | Substituierte Sulfonylamino(thio)carbonylverbindungen |
| US5977117A (en) * | 1996-01-05 | 1999-11-02 | Texas Biotechnology Corporation | Substituted phenyl compounds and derivatives thereof that modulate the activity of endothelin |
| US5856507A (en) * | 1997-01-21 | 1999-01-05 | Bristol-Myers Squibb Co. | Methods for the preparation of biphenyl isoxazole sulfonamides |
| NZ330464A (en) * | 1996-02-20 | 2000-04-28 | Bristol Myers Squibb Co | Methods for the preparation of biphenyl isoxazole sulfonamides |
| US5958905A (en) * | 1996-03-26 | 1999-09-28 | Texas Biotechnology Corporation | Phosphoramidates, phosphinic amides and related compounds and the use thereof to modulate the activity of endothelin |
| US5939446A (en) * | 1996-04-09 | 1999-08-17 | Bristol-Myers Squibb Co. | Heteroaryl substituted phenyl isoxazole sulfonamide endothelin antagonists |
| US5804585A (en) * | 1996-04-15 | 1998-09-08 | Texas Biotechnology Corporation | Thieno-pyridine sulfonamides derivatives thereof and related compounds that modulate the activity of endothelin |
| US5877193A (en) * | 1996-07-19 | 1999-03-02 | Hoffmann-La Roche Inc. | Use of N-(4-aryl-thiazol-2-yl)-sulfonamides |
| TW536540B (en) * | 1997-01-30 | 2003-06-11 | Bristol Myers Squibb Co | Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe |
| AU6187898A (en) * | 1997-01-30 | 1998-08-25 | Bristol-Myers Squibb Company | Method for preventing or treating low renin hypertension by administering an endothelin antagonist |
| US6432994B1 (en) * | 1997-04-28 | 2002-08-13 | Texas Biotechnology Corporation | Sulfonamides for treatment of endothelin-mediated disorders |
| US5783705A (en) | 1997-04-28 | 1998-07-21 | Texas Biotechnology Corporation | Process of preparing alkali metal salys of hydrophobic sulfonamides |
| EP1165472A4 (en) | 1999-03-19 | 2002-11-20 | Bristol Myers Squibb Co | METHOD FOR PRODUCING BIPHENYL ISOXAZOLE |
| US7566452B1 (en) | 1999-05-04 | 2009-07-28 | New York University | Cancer treatment with endothelin receptor antagonists |
| EP1741713A3 (en) * | 1999-12-15 | 2009-09-09 | Bristol-Myers Squibb Company | Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists |
| EE200200363A (et) * | 1999-12-31 | 2003-08-15 | Texas Biotechnology Corporation | Sulfoonamiidid ja nende derivaadid, mis moduleerivad endoteliini aktiivsust |
| EP1160248A1 (en) * | 2000-05-31 | 2001-12-05 | Pfizer Inc. | N-(Isoxazol-5-yl)-sulfonamide derivatives and their use as endothelin antagonists |
| US6639082B2 (en) | 2000-10-17 | 2003-10-28 | Bristol-Myers Squibb Company | Methods for the preparation of biphenyl isoxazole sulfonamides |
| DK1369419T3 (da) * | 2001-03-12 | 2007-09-24 | Ono Pharmaceutical Co | N-phenylarylsulfonamidforbindelse, lægemiddel indeholdende forbindelsen som en aktiv bestanddel, mellemprodukt for forbindelsen og fremgangmåder til fremstilling heraf |
| GB0219660D0 (en) | 2002-08-23 | 2002-10-02 | Astrazeneca Ab | Therapeutic use |
| GB0403744D0 (en) | 2004-02-20 | 2004-03-24 | Astrazeneca Ab | Chemical process |
| MX2007004862A (es) * | 2004-10-29 | 2007-05-09 | Astrazeneca Ab | Nuevos derivados de sulfonamida como moduladores del receptor de glucocorticoides para el tratamiento de enfermedades inflamatorias. |
| MX2008006530A (es) | 2005-11-22 | 2008-09-25 | Amgen Inc | Inhibidores de 11-beta-hidroxiesteroide deshidrogenasa tipo 1. |
| TW200800150A (en) * | 2005-12-21 | 2008-01-01 | Organon Nv | Compounds with medicinal effects due to interaction with the glucocorticoid receptor |
| CA2659155A1 (en) | 2006-07-20 | 2008-01-24 | Amgen Inc. | Substituted azole aromatic heterocycles as inhibitors of 11.beta.-hsd-1 |
| TW200829578A (en) | 2006-11-23 | 2008-07-16 | Astrazeneca Ab | Chemical compounds 537 |
| JO2754B1 (en) | 2006-12-21 | 2014-03-15 | استرازينكا ايه بي | Amylendazoleil derivatives for the treatment of glucocorticoid-mediated disorders |
| SA109300309B1 (ar) | 2008-05-20 | 2013-01-22 | باير شيرنج فارما ايه جي | مشتقات فينيل وبنزو داي أوكسينيل إندازول بها استبدال |
| GEP20135992B (en) | 2009-01-12 | 2013-12-25 | Icagen Inc | Sulfonamide derivatives |
| ES2532356T3 (es) | 2010-07-09 | 2015-03-26 | Pfizer Limited | N-sulfonilbenzamidas como inhibidores de los canales de sodio dependientes de voltaje |
| TW201512171A (zh) | 2013-04-19 | 2015-04-01 | Pfizer Ltd | 化學化合物 |
| GB201721185D0 (en) | 2017-12-18 | 2018-01-31 | Nodthera Ltd | Sulphonyl urea derivatives |
| GB201810092D0 (en) | 2018-06-20 | 2018-08-08 | Ctxt Pty Ltd | Compounds |
| GB201810581D0 (en) | 2018-06-28 | 2018-08-15 | Ctxt Pty Ltd | Compounds |
| HUE067378T2 (hu) | 2019-06-12 | 2024-10-28 | Nodthera Ltd | Szulfonilurea származékok és alkalmazásaik |
| EP3983388A1 (en) * | 2019-06-12 | 2022-04-20 | Nodthera Limited | Sulfonamide derivatives and uses thereof |
| PL4299135T3 (pl) | 2019-06-18 | 2025-11-12 | Pfizer Inc. | Pochodne benzizoksazolosulfonamidu |
| US20240287053A1 (en) * | 2021-06-22 | 2024-08-29 | Alchemedicine, Inc. | Compound, endothelin-a receptor antagonist, and pharmaceutical composition |
| JP2025183466A (ja) * | 2022-11-11 | 2025-12-17 | 株式会社アークメディスン | 化合物、エンドセリンａ受容体拮抗剤、アンジオテンシンｉｉタイプ１受容体拮抗剤及び医薬組成物 |
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|---|---|---|---|---|
| NO117180B (enExample) * | 1963-12-23 | 1969-07-14 | Shionogi & Co | |
| US3422095A (en) * | 1966-11-04 | 1969-01-14 | Hoffmann La Roche | N**1-and/or n**4-(lower alkoxyacetyl) sulfanilamides |
| US5284828A (en) * | 1990-05-14 | 1994-02-08 | Fujisawa Pharmaceutical Co. Ltd. | Peptide compound and its preparation |
| TW270116B (enExample) * | 1991-04-25 | 1996-02-11 | Hoffmann La Roche | |
| 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 |
| US5305312A (en) * | 1992-02-07 | 1994-04-19 | At&T Bell Laboratories | Apparatus for interfacing analog telephones and digital data terminals to an ISDN line |
| TW224462B (enExample) * | 1992-02-24 | 1994-06-01 | Squibb & Sons Inc |
-
1993
- 1993-04-20 NZ NZ247440A patent/NZ247440A/en unknown
- 1993-04-21 IL IL10548193A patent/IL105481A/en not_active IP Right Cessation
- 1993-04-26 ZA ZA932914A patent/ZA932914B/xx unknown
- 1993-04-28 JP JP10235493A patent/JP3286391B2/ja not_active Expired - Fee Related
- 1993-04-29 ES ES93303373T patent/ES2100459T3/es not_active Expired - Lifetime
- 1993-04-29 DE DE69308229T patent/DE69308229T2/de not_active Expired - Fee Related
- 1993-04-29 AT AT93303373T patent/ATE149155T1/de not_active IP Right Cessation
- 1993-04-29 DK DK93303373.0T patent/DK0569193T3/da active
- 1993-04-29 EP EP93303373A patent/EP0569193B1/en not_active Expired - Lifetime
- 1993-04-29 CA CA002095174A patent/CA2095174A1/en not_active Abandoned
- 1993-05-04 MX MX9302618A patent/MX9302618A/es not_active IP Right Cessation
- 1993-05-04 KR KR1019930007628A patent/KR100277454B1/ko not_active Expired - Fee Related
- 1993-05-05 NO NO931638A patent/NO303065B1/no not_active IP Right Cessation
- 1993-05-05 AU AU38382/93A patent/AU659545B2/en not_active Ceased
- 1993-05-05 PL PL93298828A patent/PL178165B1/pl unknown
- 1993-05-05 RU RU93004992A patent/RU2133742C1/ru not_active IP Right Cessation
- 1993-05-05 HU HU9301305A patent/HU218938B/hu not_active IP Right Cessation
- 1993-05-06 CN CN93107073A patent/CN1066441C/zh not_active Expired - Fee Related
- 1993-05-06 FI FI932052A patent/FI112655B/fi not_active IP Right Cessation
-
1997
- 1997-05-15 GR GR970401070T patent/GR3023421T3/el unknown
- 1997-06-26 HK HK98197A patent/HK98197A/en not_active IP Right Cessation
-
1998
- 1998-02-20 CY CY201698A patent/CY2016A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5726194A (en) * | 1995-03-18 | 1998-03-10 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Endothelin receptor antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| KR930023337A (ko) | 1993-12-18 |
| FI932052A0 (fi) | 1993-05-06 |
| JPH0649046A (ja) | 1994-02-22 |
| PL298828A1 (en) | 1993-12-27 |
| KR100277454B1 (ko) | 2001-01-15 |
| NO931638D0 (no) | 1993-05-05 |
| RU2133742C1 (ru) | 1999-07-27 |
| HU218938B (hu) | 2001-01-29 |
| MX9302618A (es) | 1994-05-31 |
| CY2016A (en) | 1998-02-20 |
| HUT65751A (en) | 1994-07-28 |
| JP3286391B2 (ja) | 2002-05-27 |
| CN1066441C (zh) | 2001-05-30 |
| FI932052L (fi) | 1993-11-07 |
| FI112655B (fi) | 2003-12-31 |
| ES2100459T3 (es) | 1997-06-16 |
| IL105481A0 (en) | 1993-08-18 |
| PL178165B1 (pl) | 2000-03-31 |
| AU659545B2 (en) | 1995-05-18 |
| EP0569193A1 (en) | 1993-11-10 |
| NO303065B1 (no) | 1998-05-25 |
| AU3838293A (en) | 1993-11-11 |
| NO931638L (no) | 1993-11-08 |
| GR3023421T3 (en) | 1997-08-29 |
| NZ247440A (en) | 1995-04-27 |
| ATE149155T1 (de) | 1997-03-15 |
| CN1084515A (zh) | 1994-03-30 |
| HU9301305D0 (en) | 1993-09-28 |
| DE69308229D1 (de) | 1997-04-03 |
| HK98197A (en) | 1997-08-08 |
| IL105481A (en) | 1996-12-05 |
| ZA932914B (en) | 1993-11-12 |
| EP0569193B1 (en) | 1997-02-26 |
| DE69308229T2 (de) | 1997-07-17 |
| DK0569193T3 (enExample) | 1997-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20041025 |