RU2091379C1 - Дифенилметилпиперазиновые производные или их фармацевтически приемлемая соль - Google Patents
Дифенилметилпиперазиновые производные или их фармацевтически приемлемая соль Download PDFInfo
- Publication number
- RU2091379C1 RU2091379C1 RU9192016555A RU92016555A RU2091379C1 RU 2091379 C1 RU2091379 C1 RU 2091379C1 RU 9192016555 A RU9192016555 A RU 9192016555A RU 92016555 A RU92016555 A RU 92016555A RU 2091379 C1 RU2091379 C1 RU 2091379C1
- Authority
- RU
- Russia
- Prior art keywords
- formula
- pharmaceutically acceptable
- derivatives
- diphenylmethylpiperazine
- diphenylmethyl
- Prior art date
Links
- 150000008640 diphenylmethylpiperazines Chemical class 0.000 title claims abstract description 18
- 150000003839 salts Chemical class 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 abstract description 33
- 239000003814 drug Substances 0.000 abstract description 21
- 238000000034 method Methods 0.000 abstract description 20
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 11
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract description 10
- 239000004593 Epoxy Substances 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 210000004165 myocardium Anatomy 0.000 description 25
- 229940079593 drug Drugs 0.000 description 18
- 206010028320 muscle necrosis Diseases 0.000 description 18
- 206010000891 acute myocardial infarction Diseases 0.000 description 16
- 230000002401 inhibitory effect Effects 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 9
- 230000001848 cardiodepressant effect Effects 0.000 description 8
- -1 inorganic acid salts Chemical class 0.000 description 8
- 230000002265 prevention Effects 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 125000004193 piperazinyl group Chemical group 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 206010028851 Necrosis Diseases 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 208000010125 myocardial infarction Diseases 0.000 description 5
- 230000017074 necrotic cell death Effects 0.000 description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- PNBNIKKSFYNIFB-UHFFFAOYSA-N 1-benzhydryl-4-(oxiran-2-ylmethyl)piperazine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1CC1CO1 PNBNIKKSFYNIFB-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical compound C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 230000004217 heart function Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 210000005240 left ventricle Anatomy 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000010561 standard procedure Methods 0.000 description 4
- OBDIDGKANKNXDV-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)-3,4-dihydro-1h-isoquinoline Chemical compound C1CC2=CC=CC=C2CN1CC1CO1 OBDIDGKANKNXDV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- 230000010412 perfusion Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- LZAYOZUFUAMFLD-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-hydroxypiperidine Chemical compound C=1C=C(Cl)C=CC=1C1(O)CCNCC1 LZAYOZUFUAMFLD-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 230000030833 cell death Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000434 field desorption mass spectrometry Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- FEDJGPQLLNQAIY-UHFFFAOYSA-N 2-[(6-oxo-1h-pyridazin-3-yl)oxy]acetic acid Chemical compound OC(=O)COC=1C=CC(=O)NN=1 FEDJGPQLLNQAIY-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 206010003225 Arteriospasm coronary Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CAVRFJRTYOKPCS-UHFFFAOYSA-N CCc1ccc(C2(CCCCC2)O)cc1 Chemical compound CCc1ccc(C2(CCCCC2)O)cc1 CAVRFJRTYOKPCS-UHFFFAOYSA-N 0.000 description 1
- 208000004434 Calcinosis Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 101100302210 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) RNR1 gene Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 208000037849 arterial hypertension Diseases 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- HDRXZJPWHTXQRI-BHDTVMLSSA-N diltiazem hydrochloride Chemical compound [Cl-].C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CC[NH+](C)C)C2=CC=CC=C2S1 HDRXZJPWHTXQRI-BHDTVMLSSA-N 0.000 description 1
- 229960005316 diltiazem hydrochloride Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (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)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Luminescent Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP182092/90 | 1990-07-10 | ||
| JP2182095A JP2651043B2 (ja) | 1990-07-10 | 1990-07-10 | ジフェニルメチルピペラジン誘導体 |
| JP182095/1990 | 1990-07-10 | ||
| PCT/JP1991/000924 WO1992000962A1 (en) | 1990-07-10 | 1991-07-10 | Diphenylmethylpiperazine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU92016555A RU92016555A (ru) | 1996-08-10 |
| RU2091379C1 true RU2091379C1 (ru) | 1997-09-27 |
Family
ID=16112265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU9192016555A RU2091379C1 (ru) | 1990-07-10 | 1991-07-10 | Дифенилметилпиперазиновые производные или их фармацевтически приемлемая соль |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5304558A (enExample) |
| EP (1) | EP0541802B1 (enExample) |
| JP (1) | JP2651043B2 (enExample) |
| CN (1) | CN1037840C (enExample) |
| AT (1) | ATE112764T1 (enExample) |
| AU (1) | AU8212591A (enExample) |
| CA (1) | CA2087032C (enExample) |
| DE (1) | DE69104615T2 (enExample) |
| RU (1) | RU2091379C1 (enExample) |
| TW (1) | TW198717B (enExample) |
| WO (1) | WO1992000962A1 (enExample) |
| ZA (1) | ZA915366B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2315763C2 (ru) * | 2001-09-06 | 2008-01-27 | Шеринг Корпорейшн | Соединение и фармацевтическая композиция |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2144669A1 (en) * | 1994-03-29 | 1995-09-30 | Kozo Akasaka | Biphenyl derivatives |
| US5658963A (en) * | 1995-02-02 | 1997-08-19 | Bisco, Inc. | One-component primer/bonding-resin systems |
| CA2385996C (en) | 1999-09-30 | 2008-02-12 | Noboru Kaneko | Anticancer agents |
| AU2001239469A1 (en) * | 2000-03-31 | 2001-10-08 | Pfizer Products Inc. | Novel piperazine derivatives |
| US8022058B2 (en) | 2000-05-10 | 2011-09-20 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the RyR receptors |
| US7718644B2 (en) * | 2004-01-22 | 2010-05-18 | The Trustees Of Columbia University In The City Of New York | Anti-arrhythmic and heart failure drugs that target the leak in the ryanodine receptor (RyR2) and uses thereof |
| US20040229781A1 (en) * | 2000-05-10 | 2004-11-18 | Marks Andrew Robert | Compounds and methods for treating and preventing exercise-induced cardiac arrhythmias |
| US20040048780A1 (en) * | 2000-05-10 | 2004-03-11 | The Trustees Of Columbia University In The City Of New York | Method for treating and preventing cardiac arrhythmia |
| US7879840B2 (en) * | 2005-08-25 | 2011-02-01 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the RyR receptors |
| US7393652B2 (en) * | 2000-05-10 | 2008-07-01 | The Trustees Of Columbia University In The City Of New York | Methods for identifying a chemical compound that directly enhances binding of FKBP12.6 to PKA-phosphorylated type 2 ryanodine receptor (RyR2) |
| US20060293266A1 (en) * | 2000-05-10 | 2006-12-28 | The Trustees Of Columbia | Phosphodiesterase 4D in the ryanodine receptor complex protects against heart failure |
| US6489125B1 (en) * | 2000-05-10 | 2002-12-03 | The Trustees Of Columbia University In The City Of New York | Methods for identifying chemical compounds that inhibit dissociation of FKBP12.6 binding protein from type 2 ryanodine receptor |
| US7544678B2 (en) * | 2002-11-05 | 2009-06-09 | The Trustees Of Columbia University In The City Of New York | Anti-arrythmic and heart failure drugs that target the leak in the ryanodine receptor (RyR2) |
| AU2004220548A1 (en) | 2003-03-07 | 2004-09-23 | The Trustees Of Columbia University, In The City Of New York | Type 1 ryanodine receptor-based methods |
| US8710045B2 (en) * | 2004-01-22 | 2014-04-29 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the ryanodine receptors |
| US7704990B2 (en) * | 2005-08-25 | 2010-04-27 | The Trustees Of Columbia University In The City Of New York | Agents for preventing and treating disorders involving modulation of the RyR receptors |
| JP5318938B2 (ja) | 2011-06-09 | 2013-10-16 | 株式会社アエタスファルマ | ジフェニルメチルピペラジン誘導体、及びそれを用いた医薬組成物 |
| JP6021616B2 (ja) * | 2012-12-04 | 2016-11-09 | 株式会社アエタスファルマ | ３−ピペラジニル−１−ピペリジニル−プロパン誘導体及びそれを含有してなる医薬組成物 |
| KR102257892B1 (ko) | 2014-11-26 | 2021-05-28 | 삼성전자주식회사 | 개선된 ｎｆｃ 안테나 및 그 안테나를 갖는 전자 장치 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR65270B (en) * | 1978-10-10 | 1980-07-31 | Fujisawa Pharmaceutical Co | Isatin derivatives and processes for the preparation thereof |
| DE3536797A1 (de) * | 1985-10-16 | 1987-04-16 | Studiengesellschaft Kohle Mbh | Verfahren zur herstellung von halogen-magnesium-alanat und dessen verwendung |
| JPS62192381A (ja) * | 1986-02-14 | 1987-08-22 | サンド・アクチエンゲゼルシヤフト | プリン誘導体類、その製造方法およびそれらを含有する医薬品 |
| NL8700245A (nl) * | 1986-02-14 | 1987-09-01 | Sandoz Ag | Purinederivaten, werkwijzen voor hun bereiding en geneesmiddelen die deze derivaten bevatten. |
| US4885300A (en) * | 1988-03-03 | 1989-12-05 | Ortho Pharmaceutical Corporation | 4-Substituted pyrazolo[3,4-D]pyrimidine derivatives |
| US5215987A (en) * | 1990-04-23 | 1993-06-01 | Ortho Pharmaceutical Corporation | Substituted benzhydryl 2-hydroxypropyl piperazine derivatives |
-
1990
- 1990-07-10 JP JP2182095A patent/JP2651043B2/ja not_active Expired - Lifetime
-
1991
- 1991-07-10 AT AT91912316T patent/ATE112764T1/de not_active IP Right Cessation
- 1991-07-10 EP EP91912316A patent/EP0541802B1/en not_active Expired - Lifetime
- 1991-07-10 WO PCT/JP1991/000924 patent/WO1992000962A1/ja not_active Ceased
- 1991-07-10 RU RU9192016555A patent/RU2091379C1/ru active
- 1991-07-10 DE DE69104615T patent/DE69104615T2/de not_active Expired - Lifetime
- 1991-07-10 CA CA002087032A patent/CA2087032C/en not_active Expired - Lifetime
- 1991-07-10 US US07/958,366 patent/US5304558A/en not_active Expired - Lifetime
- 1991-07-10 ZA ZA915366A patent/ZA915366B/xx unknown
- 1991-07-10 AU AU82125/91A patent/AU8212591A/en not_active Abandoned
- 1991-07-10 CN CN91105588A patent/CN1037840C/zh not_active Expired - Lifetime
- 1991-09-03 TW TW080106989A patent/TW198717B/zh not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| Патент ЕПВ N 0010398, кл. C 07 D 209/38, 1980. Патент США N 4382934, кл. A 61 K 31/495, 1982. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2315763C2 (ru) * | 2001-09-06 | 2008-01-27 | Шеринг Корпорейшн | Соединение и фармацевтическая композиция |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1992000962A1 (en) | 1992-01-23 |
| US5304558A (en) | 1994-04-19 |
| CA2087032A1 (en) | 1992-01-11 |
| DE69104615T2 (de) | 1995-03-23 |
| ZA915366B (en) | 1992-04-29 |
| EP0541802A4 (en) | 1993-05-26 |
| JP2651043B2 (ja) | 1997-09-10 |
| AU8212591A (en) | 1992-02-04 |
| DE69104615D1 (de) | 1994-11-17 |
| ATE112764T1 (de) | 1994-10-15 |
| EP0541802B1 (en) | 1994-10-12 |
| CN1037840C (zh) | 1998-03-25 |
| CA2087032C (en) | 1999-06-15 |
| TW198717B (enExample) | 1993-01-21 |
| JPH0469377A (ja) | 1992-03-04 |
| CN1058963A (zh) | 1992-02-26 |
| EP0541802A1 (en) | 1993-05-19 |
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