CA2560336A1 - Benzofuranyl derivatives useful for the treatment of cardiac arrhythmia - Google Patents
Benzofuranyl derivatives useful for the treatment of cardiac arrhythmia Download PDFInfo
- Publication number
- CA2560336A1 CA2560336A1 CA002560336A CA2560336A CA2560336A1 CA 2560336 A1 CA2560336 A1 CA 2560336A1 CA 002560336 A CA002560336 A CA 002560336A CA 2560336 A CA2560336 A CA 2560336A CA 2560336 A1 CA2560336 A1 CA 2560336A1
- Authority
- CA
- Canada
- Prior art keywords
- compounds
- diiodo
- benzofuran
- ethoxy
- benzoyl
- 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
- 206010003119 arrhythmia Diseases 0.000 title claims abstract description 26
- 238000011282 treatment Methods 0.000 title abstract description 14
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- SOVKDXSMTOVVFW-UHFFFAOYSA-N 2-[3-[4-(2-aminoethoxy)-3,5-diiodobenzoyl]-1-benzofuran-2-yl]acetic acid Chemical compound C1=C(I)C(OCCN)=C(I)C=C1C(=O)C1=C(CC(O)=O)OC2=CC=CC=C12 SOVKDXSMTOVVFW-UHFFFAOYSA-N 0.000 claims description 2
- CTJZIVGEPIKKTD-CQSZACIVSA-N [(2r)-3-methylbutan-2-yl] 2-[3-[4-(2-aminoethoxy)-3,5-diiodobenzoyl]-1-benzofuran-2-yl]acetate Chemical compound CC(C)[C@@H](C)OC(=O)CC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCCN)C(I)=C1 CTJZIVGEPIKKTD-CQSZACIVSA-N 0.000 claims description 2
- XAEKWMSRRZNFQR-MRXNPFEDSA-N [(2r)-3-methylbutan-2-yl] 2-[3-[4-[2-(ethylamino)ethoxy]-3,5-diiodobenzoyl]-1-benzofuran-2-yl]acetate Chemical compound C1=C(I)C(OCCNCC)=C(I)C=C1C(=O)C1=C(CC(=O)O[C@H](C)C(C)C)OC2=CC=CC=C12 XAEKWMSRRZNFQR-MRXNPFEDSA-N 0.000 claims description 2
- AXKHDUDENWKNNO-CYBMUJFWSA-N [(2r)-butan-2-yl] 2-[3-[4-(2-aminoethoxy)-3,5-diiodobenzoyl]-1-benzofuran-2-yl]acetate Chemical compound CC[C@@H](C)OC(=O)CC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCCN)C(I)=C1 AXKHDUDENWKNNO-CYBMUJFWSA-N 0.000 claims description 2
- CTJZIVGEPIKKTD-AWEZNQCLSA-N [(2s)-3-methylbutan-2-yl] 2-[3-[4-(2-aminoethoxy)-3,5-diiodobenzoyl]-1-benzofuran-2-yl]acetate Chemical compound CC(C)[C@H](C)OC(=O)CC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCCN)C(I)=C1 CTJZIVGEPIKKTD-AWEZNQCLSA-N 0.000 claims description 2
- XAEKWMSRRZNFQR-INIZCTEOSA-N [(2s)-3-methylbutan-2-yl] 2-[3-[4-[2-(ethylamino)ethoxy]-3,5-diiodobenzoyl]-1-benzofuran-2-yl]acetate Chemical compound C1=C(I)C(OCCNCC)=C(I)C=C1C(=O)C1=C(CC(=O)O[C@@H](C)C(C)C)OC2=CC=CC=C12 XAEKWMSRRZNFQR-INIZCTEOSA-N 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- PFCZBLNPHPEGKS-UHFFFAOYSA-N 2-[3-[4-[2-(ethylamino)ethoxy]-3,5-diiodobenzoyl]-1-benzofuran-2-yl]acetic acid Chemical compound C1=C(I)C(OCCNCC)=C(I)C=C1C(=O)C1=C(CC(O)=O)OC2=CC=CC=C12 PFCZBLNPHPEGKS-UHFFFAOYSA-N 0.000 claims 1
- IWIWNBHRTHUJNF-OAHLLOKOSA-N [(2r)-butan-2-yl] 2-[3-[4-[2-(ethylamino)ethoxy]-3,5-diiodobenzoyl]-1-benzofuran-2-yl]acetate Chemical compound C1=C(I)C(OCCNCC)=C(I)C=C1C(=O)C1=C(CC(=O)O[C@H](C)CC)OC2=CC=CC=C12 IWIWNBHRTHUJNF-OAHLLOKOSA-N 0.000 claims 1
- AXKHDUDENWKNNO-ZDUSSCGKSA-N [(2s)-butan-2-yl] 2-[3-[4-(2-aminoethoxy)-3,5-diiodobenzoyl]-1-benzofuran-2-yl]acetate Chemical compound CC[C@H](C)OC(=O)CC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCCN)C(I)=C1 AXKHDUDENWKNNO-ZDUSSCGKSA-N 0.000 claims 1
- IWIWNBHRTHUJNF-HNNXBMFYSA-N [(2s)-butan-2-yl] 2-[3-[4-[2-(ethylamino)ethoxy]-3,5-diiodobenzoyl]-1-benzofuran-2-yl]acetate Chemical compound C1=C(I)C(OCCNCC)=C(I)C=C1C(=O)C1=C(CC(=O)O[C@@H](C)CC)OC2=CC=CC=C12 IWIWNBHRTHUJNF-HNNXBMFYSA-N 0.000 claims 1
- -1 1 to 4 Chemical class 0.000 description 35
- 125000003118 aryl group Chemical group 0.000 description 28
- 206010019280 Heart failures Diseases 0.000 description 22
- 230000000694 effects Effects 0.000 description 22
- 206010007559 Cardiac failure congestive Diseases 0.000 description 21
- 125000000623 heterocyclic group Chemical group 0.000 description 20
- ITPDYQOUSLNIHG-UHFFFAOYSA-N Amiodarone hydrochloride Chemical compound [Cl-].CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCC[NH+](CC)CC)C(I)=C1 ITPDYQOUSLNIHG-UHFFFAOYSA-N 0.000 description 19
- 229960005260 amiodarone Drugs 0.000 description 19
- 125000001072 heteroaryl group Chemical group 0.000 description 16
- 229940079593 drug Drugs 0.000 description 15
- 239000003814 drug Substances 0.000 description 15
- 239000003416 antiarrhythmic agent Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 206010047302 ventricular tachycardia Diseases 0.000 description 11
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 10
- 230000008901 benefit Effects 0.000 description 10
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- 125000001424 substituent group Chemical group 0.000 description 10
- 230000006793 arrhythmia Effects 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 230000002861 ventricular Effects 0.000 description 7
- 208000001871 Tachycardia Diseases 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
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- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
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- 125000004043 oxo group Chemical group O=* 0.000 description 6
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- 239000012659 cardioprotective agent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 206010042600 Supraventricular arrhythmias Diseases 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 230000003288 anthiarrhythmic effect Effects 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
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- 230000037361 pathway Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 4
- 230000013577 regulation of ventricular cardiomyocyte membrane repolarization Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 206010003658 Atrial Fibrillation Diseases 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- 241000282412 Homo Species 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
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- 206010042434 Sudden death Diseases 0.000 description 3
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- 239000004480 active ingredient Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 230000000747 cardiac effect Effects 0.000 description 3
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- 238000007257 deesterification reaction Methods 0.000 description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000000160 oxazolidinyl group Chemical group 0.000 description 3
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- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- QNNHQVPFZIFNFK-UHFFFAOYSA-N oxazolo[4,5-b]pyridine Chemical compound C1=CC=C2OC=NC2=N1 QNNHQVPFZIFNFK-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000005954 phenoxathiinyl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004928 piperidonyl group Chemical group 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 description 1
- 229960000244 procainamide Drugs 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229960005202 streptokinase Drugs 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000440 toxicity profile Toxicity 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 150000003672 ureas Chemical group 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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
- C07D307/80—Radicals substituted by oxygen atoms
-
- 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
-
- 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
- A61K31/343—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 condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
-
- 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
- A61P9/06—Antiarrhythmics
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56091704P | 2004-04-09 | 2004-04-09 | |
| US60/560,917 | 2004-04-09 | ||
| PCT/US2005/012138 WO2005099684A1 (en) | 2004-04-09 | 2005-04-08 | Benzofuranyl derivatives useful for the treatment of cardiac arrhythmia |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2560336A1 true CA2560336A1 (en) | 2005-10-27 |
Family
ID=34965215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002560336A Abandoned CA2560336A1 (en) | 2004-04-09 | 2005-04-08 | Benzofuranyl derivatives useful for the treatment of cardiac arrhythmia |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US7105568B2 (enExample) |
| EP (1) | EP1732537A1 (enExample) |
| JP (1) | JP2007532576A (enExample) |
| KR (1) | KR20070001259A (enExample) |
| CN (1) | CN1950080A (enExample) |
| AU (1) | AU2005232701A1 (enExample) |
| BR (1) | BRPI0509740A (enExample) |
| CA (1) | CA2560336A1 (enExample) |
| IL (1) | IL178127A0 (enExample) |
| MX (1) | MXPA06011647A (enExample) |
| NO (1) | NO20065156L (enExample) |
| RU (1) | RU2373199C2 (enExample) |
| WO (1) | WO2005099684A1 (enExample) |
| ZA (1) | ZA200607666B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2373199C2 (ru) * | 2004-04-09 | 2009-11-20 | Арикс Терапьютикс | Производные бензофурана, композиции на их основе и способы лечения аритмии сердца |
| RU2446143C2 (ru) * | 2010-05-19 | 2012-03-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Ярославский государственный технический университет" (ЯГТУ) | Способ получения эфиров замещенных 5,6-дицианобензофуран-2-карбоновых кислот |
| CN108396016B (zh) * | 2018-02-05 | 2021-05-25 | 中国科学院南海海洋研究所 | 一种酯酶phe21及其编码基因和在手性乙酸仲丁酯制备中的应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2550091B1 (fr) * | 1983-08-02 | 1986-05-23 | Sanofi Sa | Composition pharmaceutique ou veterinaire destinee a combattre des troubles ischemiques cardiaques contenant un derive du benzofuranne |
| US5175187A (en) * | 1989-03-06 | 1992-12-29 | Soorianarain Baligadoo | Synergistic compositions for the treatment of coronary insufficiency and methods of use thereof |
| US5364880A (en) * | 1993-06-16 | 1994-11-15 | Advanced Therapies, Inc. | Compound for treatment of cardiac arrhythmia, synthesis, and methods of use |
| US6309823B1 (en) * | 1993-10-26 | 2001-10-30 | Affymetrix, Inc. | Arrays of nucleic acid probes for analyzing biotransformation genes and methods of using the same |
| US6121278A (en) * | 1997-09-03 | 2000-09-19 | Guilford Pharmaceuticals, Inc. | Di-n-heterocyclic compounds, methods, and compositions for inhibiting parp activity |
| RU2138492C1 (ru) * | 1997-12-23 | 1999-09-27 | Пятигорская государственная фармацевтическая академия | Способ синтеза производных 3-(5-метилфур-2-ил)-бензофурана, обладающих гипотензивной, антиангинальной и антиаритмической активностями |
| ATE369351T1 (de) * | 1999-10-15 | 2007-08-15 | Aryx Therapeutics | Enantiomere verbindungen zur behandlung von herzrythmusstörungen und verfahren zu ihrer anwendung |
| EP1451169A1 (en) * | 2001-12-10 | 2004-09-01 | ARYx Therapeutics | Novel compounds for the treatment of cardiac arrhythmia, synthesis, and methods of use |
| US7015568B2 (en) * | 2003-08-21 | 2006-03-21 | Texas Instruments Incorporated | System for ultraviolet atmospheric seed layer remediation |
| RU2373199C2 (ru) * | 2004-04-09 | 2009-11-20 | Арикс Терапьютикс | Производные бензофурана, композиции на их основе и способы лечения аритмии сердца |
-
2005
- 2005-04-08 RU RU2006139649/04A patent/RU2373199C2/ru not_active IP Right Cessation
- 2005-04-08 MX MXPA06011647A patent/MXPA06011647A/es active IP Right Grant
- 2005-04-08 KR KR1020067022953A patent/KR20070001259A/ko not_active Ceased
- 2005-04-08 JP JP2007507557A patent/JP2007532576A/ja not_active Abandoned
- 2005-04-08 EP EP05735166A patent/EP1732537A1/en not_active Ceased
- 2005-04-08 AU AU2005232701A patent/AU2005232701A1/en not_active Abandoned
- 2005-04-08 BR BRPI0509740-1A patent/BRPI0509740A/pt not_active IP Right Cessation
- 2005-04-08 CA CA002560336A patent/CA2560336A1/en not_active Abandoned
- 2005-04-08 US US11/101,995 patent/US7105568B2/en not_active Expired - Lifetime
- 2005-04-08 CN CNA200580012140XA patent/CN1950080A/zh active Pending
- 2005-04-08 WO PCT/US2005/012138 patent/WO2005099684A1/en not_active Ceased
-
2006
- 2006-06-12 US US11/423,559 patent/US7351842B2/en not_active Expired - Fee Related
- 2006-09-13 ZA ZA200607666A patent/ZA200607666B/en unknown
- 2006-09-14 IL IL178127A patent/IL178127A0/en unknown
- 2006-11-09 NO NO20065156A patent/NO20065156L/no not_active Application Discontinuation
-
2007
- 2007-11-07 US US11/936,620 patent/US20080114059A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20060276535A1 (en) | 2006-12-07 |
| US20080114059A1 (en) | 2008-05-15 |
| CN1950080A (zh) | 2007-04-18 |
| JP2007532576A (ja) | 2007-11-15 |
| AU2005232701A1 (en) | 2005-10-27 |
| KR20070001259A (ko) | 2007-01-03 |
| US20050228045A1 (en) | 2005-10-13 |
| EP1732537A1 (en) | 2006-12-20 |
| IL178127A0 (en) | 2006-12-31 |
| NO20065156L (no) | 2006-11-09 |
| US7105568B2 (en) | 2006-09-12 |
| WO2005099684A1 (en) | 2005-10-27 |
| MXPA06011647A (es) | 2007-04-13 |
| RU2373199C2 (ru) | 2009-11-20 |
| BRPI0509740A (pt) | 2007-09-25 |
| ZA200607666B (en) | 2008-03-26 |
| US7351842B2 (en) | 2008-04-01 |
| RU2006139649A (ru) | 2008-05-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |