PT1389183E - Derivados de sulfonamida - Google Patents
Derivados de sulfonamida Download PDFInfo
- Publication number
- PT1389183E PT1389183E PT02742997T PT02742997T PT1389183E PT 1389183 E PT1389183 E PT 1389183E PT 02742997 T PT02742997 T PT 02742997T PT 02742997 T PT02742997 T PT 02742997T PT 1389183 E PT1389183 E PT 1389183E
- Authority
- PT
- Portugal
- Prior art keywords
- compound
- formula
- alkyl
- halogen
- triazol
- Prior art date
Links
- 229940124530 sulfonamide Drugs 0.000 title description 3
- 150000003456 sulfonamides Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- -1 indan-5-yl Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 108020003175 receptors Proteins 0.000 claims description 7
- 102000005962 receptors Human genes 0.000 claims description 7
- 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 6
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 101800004538 Bradykinin Proteins 0.000 claims description 5
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 claims description 5
- 102100035792 Kininogen-1 Human genes 0.000 claims description 5
- 230000004913 activation Effects 0.000 claims description 5
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 230000000144 pharmacologic effect Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 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 3
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 102000000169 Bradykinin receptor B1 Human genes 0.000 claims 1
- 108050008513 Bradykinin receptor B1 Proteins 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 208000002193 Pain Diseases 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 102000010183 Bradykinin receptor Human genes 0.000 description 4
- 108050001736 Bradykinin receptor Proteins 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- AILVBOHFGXNHCC-TZPCGENMSA-N (2s)-2-[[(2s)-1-[(2s)-2-[[(2s)-2-[[2-[[(2s)-1-[(2s)-1-[(2s)-2-[[(2s)-2,6-diaminohexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]pyrrolidine- Chemical compound NCCCC[C@H](N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)CCC1 AILVBOHFGXNHCC-TZPCGENMSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CQYBNXGHMBNGCG-FXQIFTODSA-N (2s,3as,7as)-2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCC[C@@H]2[NH2+][C@H](C(=O)[O-])C[C@@H]21 CQYBNXGHMBNGCG-FXQIFTODSA-N 0.000 description 2
- QGFRTTXMLLGTLQ-DEOSSOPVSA-N (3s)-3-[[2-[(4-bromo-2-chlorophenyl)sulfonyl-[2-(2,3-dihydro-1h-inden-5-yloxy)ethyl]amino]acetyl]amino]-4-phenylbutanoic acid Chemical compound C([C@@H](CC(=O)O)NC(=O)CN(CCOC=1C=C2CCCC2=CC=1)S(=O)(=O)C=1C(=CC(Br)=CC=1)Cl)C1=CC=CC=C1 QGFRTTXMLLGTLQ-DEOSSOPVSA-N 0.000 description 2
- LXTOBZSNMMZZGP-UHFFFAOYSA-N 2,4-dichloro-n-[2-(2,3-dihydro-1h-inden-5-yloxy)ethyl]-n-(2h-tetrazol-5-ylmethyl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)N(CC=1NN=NN=1)CCOC1=CC=C(CCC2)C2=C1 LXTOBZSNMMZZGP-UHFFFAOYSA-N 0.000 description 2
- OZOHQAFFONUYDW-UHFFFAOYSA-N 2-[(4-bromo-2-chlorophenyl)sulfonyl-[2-(2,3-dihydro-1h-inden-5-yloxy)ethyl]amino]acetic acid Chemical compound C=1C=C2CCCC2=CC=1OCCN(CC(=O)O)S(=O)(=O)C1=CC=C(Br)C=C1Cl OZOHQAFFONUYDW-UHFFFAOYSA-N 0.000 description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 2
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229940104754 Bradykinin B1 receptor antagonist Drugs 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 2
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- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical group C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 2
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 2
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- 239000003144 bradykinin B1 receptor antagonist Substances 0.000 description 2
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- 239000012043 crude product Substances 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
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- 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
- XZZXIYZZBJDEEP-UHFFFAOYSA-N imipramine hydrochloride Chemical compound [Cl-].C1CC2=CC=CC=C2N(CCC[NH+](C)C)C2=CC=CC=C21 XZZXIYZZBJDEEP-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- OICCNYDDPHVSGB-UHFFFAOYSA-N methyl 2-[(4-bromo-2-chlorophenyl)sulfonyl-[2-(2,3-dihydro-1h-inden-5-yloxy)ethyl]amino]acetate Chemical compound C=1C=C2CCCC2=CC=1OCCN(CC(=O)OC)S(=O)(=O)C1=CC=C(Br)C=C1Cl OICCNYDDPHVSGB-UHFFFAOYSA-N 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
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- YVEIGGFZKKHPSI-UHFFFAOYSA-N 2,4-dichloro-n-[[1-(2-cyanoethyl)tetrazol-5-yl]methyl]-n-[2-(2,3-dihydro-1h-inden-5-yloxy)ethyl]benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC=C1S(=O)(=O)N(CC=1N(N=NN=1)CCC#N)CCOC1=CC=C(CCC2)C2=C1 YVEIGGFZKKHPSI-UHFFFAOYSA-N 0.000 description 1
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- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29082701P | 2001-05-14 | 2001-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT1389183E true PT1389183E (pt) | 2010-04-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| PT02742997T PT1389183E (pt) | 2001-05-14 | 2002-05-13 | Derivados de sulfonamida |
Country Status (13)
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|---|---|
| US (1) | US7109203B2 (OSRAM) |
| EP (1) | EP1389183B1 (OSRAM) |
| JP (1) | JP4150597B2 (OSRAM) |
| CN (1) | CN1268610C (OSRAM) |
| AR (1) | AR035891A1 (OSRAM) |
| AT (1) | ATE459598T1 (OSRAM) |
| BR (1) | BR0209386A (OSRAM) |
| CA (1) | CA2443721A1 (OSRAM) |
| DE (1) | DE60235536D1 (OSRAM) |
| ES (1) | ES2340664T3 (OSRAM) |
| PE (1) | PE20021158A1 (OSRAM) |
| PT (1) | PT1389183E (OSRAM) |
| WO (1) | WO2002092556A1 (OSRAM) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6214807B1 (en) * | 1999-06-22 | 2001-04-10 | Cv Therapeutics, Inc. | C-pyrazole 2A A receptor agonists |
| USRE47351E1 (en) | 1999-06-22 | 2019-04-16 | Gilead Sciences, Inc. | 2-(N-pyrazolo)adenosines with application as adenosine A2A receptor agonists |
| US6403567B1 (en) | 1999-06-22 | 2002-06-11 | Cv Therapeutics, Inc. | N-pyrazole A2A adenosine receptor agonists |
| CA2671940A1 (en) * | 2000-02-23 | 2001-08-30 | Cv Therapeutics, Inc. | Identification of partial agonists of the a2a adenosine receptor |
| US7683037B2 (en) * | 2002-07-29 | 2010-03-23 | Gilead Palo Alto, Inc. | Myocardial perfusion imaging method |
| US8470801B2 (en) | 2002-07-29 | 2013-06-25 | Gilead Sciences, Inc. | Myocardial perfusion imaging methods and compositions |
| US20050020915A1 (en) * | 2002-07-29 | 2005-01-27 | Cv Therapeutics, Inc. | Myocardial perfusion imaging methods and compositions |
| US20070093485A1 (en) * | 2002-12-19 | 2007-04-26 | Elan Pharmaceuticals, Inc. | Substituted n-phenyl sulfonamide bradykinin antagonists |
| CN101076343A (zh) * | 2004-10-20 | 2007-11-21 | Cv医药有限公司 | A2a腺苷受体激动剂的应用 |
| GB0525068D0 (en) | 2005-12-08 | 2006-01-18 | Novartis Ag | Organic compounds |
| EP1989214B8 (en) | 2006-02-03 | 2016-12-21 | Gilead Sciences, Inc. | Process for preparing an a2a-adenosine receptor agonist and its polymorphs |
| JP2009541354A (ja) * | 2006-06-22 | 2009-11-26 | シーブイ・セラピューティクス・インコーポレイテッド | 虚血の治療におけるａ２ａアデノシン受容体アゴニストの使用 |
| RU2459626C2 (ru) * | 2006-09-01 | 2012-08-27 | Гайлид Сайэнсиз, Инк. | Способы и композиции, повышающие переносимость пациентом методов визуализации миокарда |
| US20090081120A1 (en) * | 2006-09-01 | 2009-03-26 | Cv Therapeutics, Inc. | Methods and Compositions for Increasing Patient Tolerability During Myocardial Imaging Methods |
| WO2008042796A2 (en) * | 2006-09-29 | 2008-04-10 | Cv Therapeutics, Inc. | Methods for myocardial imaging in patients having a history of pulmonary disease |
| WO2008086096A2 (en) * | 2007-01-03 | 2008-07-17 | Cv Therapeutics, Inc. | Myocardial perfusion imaging |
| AU2009228765B2 (en) * | 2008-03-24 | 2012-05-31 | Novartis Ag | Arylsulfonamide-based matrix metalloprotease inhibitors |
| MX2011003168A (es) * | 2008-09-29 | 2011-05-19 | Gilead Sciences Inc | Combinaciones de un agente de control de cantidad y un antagonista del receptor a-2-alfa para utilizarse en metodos de tomografia computarizada de detectores multiples. |
| EP2316820A1 (en) | 2009-10-28 | 2011-05-04 | Dompe S.p.A. | 2-aryl-propionamide derivatives useful as bradykinin receptor antagonists and pharmaceutical compositions containing them |
| AR086554A1 (es) | 2011-05-27 | 2014-01-08 | Novartis Ag | Derivados de la piperidina 3-espirociclica como agonistas de receptores de la ghrelina |
| EA201491990A1 (ru) | 2012-05-03 | 2015-02-27 | Новартис Аг | L-малатная соль 2,7-диазаспиро[4.5]дец-7-иловых производных и их кристаллические формы в качестве агонистов грелиновых рецепторов |
| PT2813502T (pt) | 2013-06-14 | 2017-04-06 | Dompé Farm S P A | Antagonistas do recetor da bradicinina e composições farmacêuticas que os contêm |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE120047C (OSRAM) * | ||||
| FR2743562B1 (fr) * | 1996-01-11 | 1998-04-03 | Sanofi Sa | Derives de n-(arylsulfonyl) aminoacides, leur preparation, les compositions pharmaceutiques en contenant |
| CN1350452A (zh) * | 1999-05-13 | 2002-05-22 | 盐野义制药株式会社 | 糖尿病的预防或治疗药 |
| GB9913079D0 (en) | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
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2002
- 2002-05-13 PT PT02742997T patent/PT1389183E/pt unknown
- 2002-05-13 CA CA002443721A patent/CA2443721A1/en not_active Abandoned
- 2002-05-13 BR BR0209386-3A patent/BR0209386A/pt not_active IP Right Cessation
- 2002-05-13 WO PCT/EP2002/005240 patent/WO2002092556A1/en not_active Ceased
- 2002-05-13 ES ES02742997T patent/ES2340664T3/es not_active Expired - Lifetime
- 2002-05-13 AR ARP020101737A patent/AR035891A1/es unknown
- 2002-05-13 AT AT02742997T patent/ATE459598T1/de not_active IP Right Cessation
- 2002-05-13 JP JP2002589442A patent/JP4150597B2/ja not_active Expired - Fee Related
- 2002-05-13 CN CNB028098900A patent/CN1268610C/zh not_active Expired - Fee Related
- 2002-05-13 US US10/475,420 patent/US7109203B2/en not_active Expired - Fee Related
- 2002-05-13 EP EP02742997A patent/EP1389183B1/en not_active Expired - Lifetime
- 2002-05-13 DE DE60235536T patent/DE60235536D1/de not_active Expired - Fee Related
- 2002-05-14 PE PE2002000401A patent/PE20021158A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1389183B1 (en) | 2010-03-03 |
| US20040127533A1 (en) | 2004-07-01 |
| JP4150597B2 (ja) | 2008-09-17 |
| JP2004528385A (ja) | 2004-09-16 |
| ATE459598T1 (de) | 2010-03-15 |
| DE60235536D1 (de) | 2010-04-15 |
| CN1268610C (zh) | 2006-08-09 |
| AR035891A1 (es) | 2004-07-21 |
| ES2340664T3 (es) | 2010-06-08 |
| WO2002092556A1 (en) | 2002-11-21 |
| CN1509269A (zh) | 2004-06-30 |
| EP1389183A1 (en) | 2004-02-18 |
| PE20021158A1 (es) | 2003-03-03 |
| US7109203B2 (en) | 2006-09-19 |
| CA2443721A1 (en) | 2002-11-21 |
| BR0209386A (pt) | 2004-07-06 |
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