CA2533492A1 - Utilisation de composes de 3,7-diazabicyclo[3,3,1]nonane pour traiter et/ou prevenir des evenements arythmiques chez des patients humains males - Google Patents
Utilisation de composes de 3,7-diazabicyclo[3,3,1]nonane pour traiter et/ou prevenir des evenements arythmiques chez des patients humains males Download PDFInfo
- Publication number
- CA2533492A1 CA2533492A1 CA002533492A CA2533492A CA2533492A1 CA 2533492 A1 CA2533492 A1 CA 2533492A1 CA 002533492 A CA002533492 A CA 002533492A CA 2533492 A CA2533492 A CA 2533492A CA 2533492 A1 CA2533492 A1 CA 2533492A1
- Authority
- CA
- Canada
- Prior art keywords
- diazabicyclo
- carbon atoms
- nonane
- group containing
- tedisamil
- 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
- 241000282414 Homo sapiens Species 0.000 title claims abstract description 69
- 238000011282 treatment Methods 0.000 title claims abstract description 27
- PTPQJKANBKHDPM-UHFFFAOYSA-N 3,7-diazabicyclo[3.3.1]nonane Chemical class C1NCC2CNCC1C2 PTPQJKANBKHDPM-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 230000003288 anthiarrhythmic effect Effects 0.000 title claims abstract description 20
- 239000003416 antiarrhythmic agent Substances 0.000 title claims abstract description 18
- 238000011321 prophylaxis Methods 0.000 title claims abstract description 10
- 206010003658 Atrial Fibrillation Diseases 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- 230000033764 rhythmic process Effects 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 25
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical class CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000012453 solvate Substances 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 12
- -1 3,7-diazabicyclo[3,3,1]nonane compound Chemical class 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000001530 fumaric acid Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006410 propenylene group Chemical group 0.000 claims description 2
- KTSZYXNHBVWNNV-UHFFFAOYSA-N 1,2-diazabicyclo[3.3.1]nonane Chemical compound C1CNN2CCCC1C2 KTSZYXNHBVWNNV-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 229960002926 tedisamil Drugs 0.000 abstract description 70
- CTIRHWCPXYGDGF-HDICACEKSA-N tedisamil Chemical compound [H][C@]12CN(CC3CC3)C[C@]([H])(CN(CC3CC3)C1)C21CCCC1 CTIRHWCPXYGDGF-HDICACEKSA-N 0.000 abstract description 54
- 238000001802 infusion Methods 0.000 description 30
- 239000000902 placebo Substances 0.000 description 25
- 229940068196 placebo Drugs 0.000 description 25
- 230000000694 effects Effects 0.000 description 15
- 241000282412 Homo Species 0.000 description 14
- AZPYPAVFNGFTGB-ORRJWUSCSA-N (1S,5R)-3,7-bis(cyclopropylmethyl)spiro[3-aza-7-azoniabicyclo[3.3.1]nonane-9,1'-cyclopentane] (E)-but-2-enedioate (E)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(=O)O.OC(=O)\C=C\C(=O)O.OC(=O)\C=C\C(=O)O.C(C1CC1)N2C[C@@H]3CN(CC4CC4)C[C@H](C2)C35CCCC5.C(C6CC6)N7C[C@@H]8CN(CC9CC9)C[C@H](C7)C8%10CCCC%10 AZPYPAVFNGFTGB-ORRJWUSCSA-N 0.000 description 13
- 238000001990 intravenous administration Methods 0.000 description 13
- 206010003662 Atrial flutter Diseases 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000013543 active substance Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 230000000977 initiatory effect Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 230000001746 atrial effect Effects 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- NXXZICGFHYJPGE-UHFFFAOYSA-N 3,7-bis(cyclopropylmethyl)spiro[3,7-diazabicyclo[3.3.1]nonane-9,1'-cyclopentane];dihydrochloride Chemical compound Cl.Cl.C1C(C23CCCC3)CN(CC3CC3)CC2CN1CC1CC1 NXXZICGFHYJPGE-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 238000013194 cardioversion Methods 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 210000002837 heart atrium Anatomy 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 208000018452 Torsade de pointes Diseases 0.000 description 3
- 208000002363 Torsades de Pointes Diseases 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000002526 effect on cardiovascular system Effects 0.000 description 3
- 239000013610 patient sample Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000013589 supplement Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 239000008215 water for injection Substances 0.000 description 3
- AOIVZQPSIHOHMP-HDICACEKSA-N (1r,5s)-7-(2-methylpropyl)-3-propan-2-ylspiro[3,7-diazabicyclo[3.3.1]nonane-9,1'-cyclohexane] Chemical compound C12([C@H]3CN(C[C@@H]2CN(C3)CC(C)C)C(C)C)CCCCC1 AOIVZQPSIHOHMP-HDICACEKSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 229920003080 Povidone K 25 Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000001174 ascending effect Effects 0.000 description 2
- 229950002035 bertosamil Drugs 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 206010061592 cardiac fibrillation Diseases 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 238000011833 dog model Methods 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 230000002600 fibrillogenic effect Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 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 2
- 230000000306 recurrent effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000007619 statistical method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 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 1
- 208000004880 Polyuria Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000002253 anti-ischaemic effect Effects 0.000 description 1
- 230000002763 arrhythmic effect Effects 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 230000003205 diastolic effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000001325 log-rank test Methods 0.000 description 1
- 238000007477 logistic regression Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 230000036279 refractory period Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4995—Pyrazines or piperazines forming part of bridged ring systems
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
La présente invention concerne l'utilisation de composés de 3,7-diazabicyclo[3,3,1]nonane, de préférence des composés de 9,9-alkylène-3,7-diazabicyclo[3,3,1]nonane, et, encore mieux, l'utilisation de tedisamil, ainsi que les sels d'addition acide et/ou les solvates de ceux-ci, acceptables d'un point de vue physiologique, pour traiter et/ou prévenir des événements anti-arythmiques chez des patients humains mâles, de préférence pour faire passer un événement de fibrillation auriculaire (Afib) ou de flutter qui vient d'apparaître à un rythme sinusal normal (NSR) chez des patients humains mâles.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03102243.7 | 2003-07-21 | ||
| EP03102243 | 2003-07-21 | ||
| PCT/EP2004/051532 WO2005011690A1 (fr) | 2003-07-21 | 2004-07-19 | Utilisation de composes de 3,7-diazabicyclo[3,3,1]nonane pour traiter et/ou prevenir des evenements arythmiques chez des patients humains males |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2533492A1 true CA2533492A1 (fr) | 2005-02-10 |
Family
ID=34112472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002533492A Abandoned CA2533492A1 (fr) | 2003-07-21 | 2004-07-19 | Utilisation de composes de 3,7-diazabicyclo[3,3,1]nonane pour traiter et/ou prevenir des evenements arythmiques chez des patients humains males |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1648456A1 (fr) |
| JP (1) | JP2006528155A (fr) |
| CN (1) | CN1822833A (fr) |
| AU (1) | AU2004260624A1 (fr) |
| BR (1) | BRPI0412247A (fr) |
| CA (1) | CA2533492A1 (fr) |
| MX (1) | MXPA06000796A (fr) |
| WO (1) | WO2005011690A1 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI577670B (zh) | 2011-05-10 | 2017-04-11 | 基利科學股份有限公司 | 充當離子通道調節劑之稠合雜環化合物 |
| NO3175985T3 (fr) | 2011-07-01 | 2018-04-28 | ||
| TWI622583B (zh) | 2011-07-01 | 2018-05-01 | 基利科學股份有限公司 | 作為離子通道調節劑之稠合雜環化合物 |
| WO2014134419A1 (fr) * | 2013-03-01 | 2014-09-04 | Gilead Sciences, Inc. | Utilisation de bloqueurs ikach pour le traitement de maladies cardiaques |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3234697A1 (de) * | 1982-09-18 | 1984-03-22 | Kali-Chemie Pharma Gmbh, 3000 Hannover | Neue diazabicyclo-(3,3,1)-nonane |
| PT88381B (pt) * | 1987-09-09 | 1995-07-06 | Kali Chemie Pharma Gmbh | Processo para a preparacao de novos compostos 3,7-diazabiciclo{3,3,1} nonano, e de composicoes farmaceuticas que contem estes compostos |
| DE4139763A1 (de) * | 1991-12-03 | 1993-06-09 | Kali-Chemie Pharma Gmbh, 3000 Hannover, De | Kristalline fumarsaure salze von 9,9-alkylen-3,7-diazabicyclononan-verbindungen und diese verbindungen enthaltende arzneimittel |
| TW200418468A (en) * | 2002-11-18 | 2004-10-01 | Solvay Pharm Gmbh | Liquid pharmaceutical formulations containing 3,7-diazabicyclo[3,3,1]nonane compounds and method of treatments relating to anti-arrhytmic events |
-
2004
- 2004-07-19 CN CNA200480019884XA patent/CN1822833A/zh active Pending
- 2004-07-19 CA CA002533492A patent/CA2533492A1/fr not_active Abandoned
- 2004-07-19 BR BRPI0412247-0A patent/BRPI0412247A/pt not_active Application Discontinuation
- 2004-07-19 JP JP2006520832A patent/JP2006528155A/ja not_active Withdrawn
- 2004-07-19 MX MXPA06000796A patent/MXPA06000796A/es not_active Application Discontinuation
- 2004-07-19 AU AU2004260624A patent/AU2004260624A1/en not_active Abandoned
- 2004-07-19 EP EP04742001A patent/EP1648456A1/fr not_active Withdrawn
- 2004-07-19 WO PCT/EP2004/051532 patent/WO2005011690A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005011690A1 (fr) | 2005-02-10 |
| EP1648456A1 (fr) | 2006-04-26 |
| AU2004260624A1 (en) | 2005-02-10 |
| CN1822833A (zh) | 2006-08-23 |
| BRPI0412247A (pt) | 2006-09-19 |
| JP2006528155A (ja) | 2006-12-14 |
| MXPA06000796A (es) | 2006-04-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20080721 |