RU2303041C2 - Твердые соли бензазепиновых соединений и их применение при получении фармацевтических соединений - Google Patents
Твердые соли бензазепиновых соединений и их применение при получении фармацевтических соединений Download PDFInfo
- Publication number
- RU2303041C2 RU2303041C2 RU2004124840/04A RU2004124840A RU2303041C2 RU 2303041 C2 RU2303041 C2 RU 2303041C2 RU 2004124840/04 A RU2004124840/04 A RU 2004124840/04A RU 2004124840 A RU2004124840 A RU 2004124840A RU 2303041 C2 RU2303041 C2 RU 2303041C2
- Authority
- RU
- Russia
- Prior art keywords
- salt
- compound
- composition
- compounds
- solution
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- -1 benzazepin compound salts Chemical class 0.000 title claims description 12
- 239000007787 solid Substances 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- 229910052751 metal Inorganic materials 0.000 claims abstract description 24
- 239000002184 metal Substances 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 9
- 239000011701 zinc Substances 0.000 claims abstract description 6
- 206010020772 Hypertension Diseases 0.000 claims abstract description 5
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 5
- 230000002496 gastric effect Effects 0.000 claims abstract description 5
- 230000002265 prevention Effects 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 17
- 239000003880 polar aprotic solvent Substances 0.000 claims description 11
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 159000000007 calcium salts Chemical class 0.000 claims description 5
- 230000003902 lesion Effects 0.000 claims description 5
- 229940009456 adriamycin Drugs 0.000 claims description 4
- 229940041181 antineoplastic drug Drugs 0.000 claims description 4
- 238000010533 azeotropic distillation Methods 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 159000000003 magnesium salts Chemical class 0.000 claims 1
- 239000012266 salt solution Substances 0.000 claims 1
- 239000011575 calcium Substances 0.000 abstract description 9
- 229910052791 calcium Inorganic materials 0.000 abstract description 6
- 239000011777 magnesium Substances 0.000 abstract description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 3
- 230000017531 blood circulation Effects 0.000 abstract description 3
- 229910052749 magnesium Inorganic materials 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052744 lithium Inorganic materials 0.000 abstract description 2
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical class N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 230000000747 cardiac effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 208000019622 heart disease Diseases 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 14
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
- VPSRQEHTHIMDQM-GZJHNZOKSA-N 2-[(3r)-3-[[(2r)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]acetic acid;hydrochloride Chemical compound Cl.C([C@H](C(=O)OCC)N[C@H]1C(N(CC(O)=O)C2=CC=CC=C2CC1)=O)CC1=CC=CC=C1 VPSRQEHTHIMDQM-GZJHNZOKSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000008259 solid foam Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 206010019280 Heart failures Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241000124008 Mammalia Species 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 102000011759 adducin Human genes 0.000 description 2
- 108010076723 adducin Proteins 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000008038 benzoazepines Chemical class 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012439 solid excipient Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000005042 acyloxymethyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000001636 atomic emission spectroscopy Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003683 cardiac damage Effects 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000003926 complexometric titration Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 230000012495 positive regulation of renal sodium excretion Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02075621.9 | 2002-01-16 | ||
| EP02075621 | 2002-01-16 | ||
| NL1019762 | 2002-01-17 | ||
| NL1019762 | 2002-01-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004124840A RU2004124840A (ru) | 2006-01-20 |
| RU2303041C2 true RU2303041C2 (ru) | 2007-07-20 |
Family
ID=26077601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004124840/04A RU2303041C2 (ru) | 2002-01-16 | 2003-01-15 | Твердые соли бензазепиновых соединений и их применение при получении фармацевтических соединений |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6998398B2 (enExample) |
| EP (1) | EP1468010A1 (enExample) |
| JP (1) | JP4384495B2 (enExample) |
| KR (1) | KR100979077B1 (enExample) |
| CN (1) | CN100591689C (enExample) |
| AU (1) | AU2003206755B2 (enExample) |
| BR (1) | BR0306701A (enExample) |
| CA (1) | CA2473447A1 (enExample) |
| HR (1) | HRP20040560A2 (enExample) |
| IL (1) | IL162645A0 (enExample) |
| MX (1) | MXPA04006887A (enExample) |
| NO (1) | NO330528B1 (enExample) |
| PL (1) | PL371511A1 (enExample) |
| RU (1) | RU2303041C2 (enExample) |
| WO (1) | WO2003059939A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2758771C1 (ru) * | 2018-01-31 | 2021-11-01 | Форту-Фоур ФАРМАЦЕУТИКАЛС Сп. з о.о. | ИНГИБИТОРЫ НЕЙТРАЛЬНОЙ ЭНДОПЕПТИДАЗЫ (НЭП) И РАСТВОРИМОЙ ЭНДОПЕПТИДАЗЫ ЧЕЛОВЕКА (РЭПч) ДЛЯ ПРОФИЛАКТИКИ И ЛЕЧЕНИЯ ГЛАЗНЫХ БОЛЕЗНЕЙ |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20050009031A (ko) * | 2003-07-15 | 2005-01-24 | 엘지전자 주식회사 | 1회 기록 가능한 광디스크 및 광디스크의 관리정보 기록방법 |
| SA04250283B1 (ar) * | 2003-09-26 | 2008-05-26 | سولفاي فارماسيتيكالز جي أم بي أتش | مشتقات من amidomethy1-substituted1-(carboxyalkyl)-cyclopentylcarbonylamino-benzazepine-N-acetic acid |
| AR046454A1 (es) * | 2003-11-18 | 2005-12-07 | Solvay Pharm Gmbh | Uso de un compuesto de acido benzazepin-n-acetico, composicion farmaceutica, y procedimiento para la produccion de dicha composicion farmaceutica |
| US20050267124A1 (en) * | 2004-05-14 | 2005-12-01 | Solvay Pharmaceuticals Gmbh | Pharmaceutical compositions comprising NEP-inhibitors, inhibitors of the endogenous producing system and PDEV inhibiitors |
| MX2007006279A (es) | 2004-12-15 | 2007-06-14 | Solvay Pharm Gmbh | Composiciones farmaceuticas que comprenden inhibidores de nep, inhibidores del sistema de produccion de endotelina endogena, e inhibidores de hmg coa-reductasa. |
| US20060159748A1 (en) * | 2004-12-23 | 2006-07-20 | Rajesh Jain | Oral immediate release formulation of a poorly water-soluble active substance |
| US20060205625A1 (en) * | 2005-02-18 | 2006-09-14 | Solvay Pharmaceuticals Gmbh | Pharmaceutical compositions comprising NEP-inhibitors, inhibitors of the endogenous endothelin producing system and diuretics |
| WO2007054975A1 (en) * | 2005-11-08 | 2007-05-18 | Panacea Biotec Ltd | Pharmaceutical compositions for the treatment of cardiovascular and other associated disorders |
| HU227696B1 (en) * | 2006-04-13 | 2011-12-28 | Egyt Gyogyszervegyeszeti Gyar | Zinc salt of rosuvastatin, process for its preparation and pharmaceutical compositions containing it |
| PL424453A1 (pl) | 2018-01-31 | 2019-08-12 | Forty-Four Pharmaceuticals Spółka Z Ograniczoną Odpowiedzialnością | Sposoby zmniejszania szkodliwego działania niedoboru perfuzji narządów miąższowych przez inhibitory obojętnej endopeptydazy (NEP) i ludzkiej rozpuszczalnej endopeptydazy (hSEP) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0830863A1 (de) * | 1996-09-18 | 1998-03-25 | Solvay Pharmaceuticals GmbH | Die gastrointestinale Durchblutung fördernde Arzneimittel |
| WO2000048601A1 (de) * | 1999-02-16 | 2000-08-24 | Solvay Pharmaceuticals Gmbh | Arzneimittel zur behandlung von bluthochdruck |
| RU2159768C2 (ru) * | 1995-03-23 | 2000-11-27 | Солвей Фармасьютикалз Гмбх | Производные бензазепин-, бензоксазепин- или бензотиазепин-n-уксусной кислоты, способ их получения и лекарственное средство, их содержащее |
| WO2001003699A1 (de) * | 1999-07-13 | 2001-01-18 | Solvay Pharmaceuticals Gmbh | Arzneimittel mit protektiver wirkung gegen oxidativ-toxische und insbesondere gegen kardiotoxische substanzen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19750002A1 (de) * | 1997-11-12 | 1999-05-20 | Solvay Pharm Gmbh | Phosphonsäure-substituierte Benzazepinon-N-essigsäurederivate sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
-
2003
- 2003-01-15 PL PL03371511A patent/PL371511A1/xx not_active Application Discontinuation
- 2003-01-15 AU AU2003206755A patent/AU2003206755B2/en not_active Ceased
- 2003-01-15 RU RU2004124840/04A patent/RU2303041C2/ru not_active IP Right Cessation
- 2003-01-15 WO PCT/EP2003/000515 patent/WO2003059939A1/en not_active Ceased
- 2003-01-15 EP EP03704436A patent/EP1468010A1/en not_active Withdrawn
- 2003-01-15 MX MXPA04006887A patent/MXPA04006887A/es active IP Right Grant
- 2003-01-15 IL IL16264503A patent/IL162645A0/xx not_active IP Right Cessation
- 2003-01-15 CN CN03802391A patent/CN100591689C/zh not_active Expired - Fee Related
- 2003-01-15 KR KR1020047010938A patent/KR100979077B1/ko not_active Expired - Fee Related
- 2003-01-15 BR BR0306701-7A patent/BR0306701A/pt not_active Application Discontinuation
- 2003-01-15 HR HR20040560A patent/HRP20040560A2/hr not_active Application Discontinuation
- 2003-01-15 CA CA002473447A patent/CA2473447A1/en not_active Abandoned
- 2003-01-15 JP JP2003560041A patent/JP4384495B2/ja not_active Expired - Lifetime
-
2004
- 2004-07-14 US US10/890,392 patent/US6998398B2/en not_active Expired - Fee Related
- 2004-08-06 NO NO20043295A patent/NO330528B1/no not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2159768C2 (ru) * | 1995-03-23 | 2000-11-27 | Солвей Фармасьютикалз Гмбх | Производные бензазепин-, бензоксазепин- или бензотиазепин-n-уксусной кислоты, способ их получения и лекарственное средство, их содержащее |
| EP0830863A1 (de) * | 1996-09-18 | 1998-03-25 | Solvay Pharmaceuticals GmbH | Die gastrointestinale Durchblutung fördernde Arzneimittel |
| WO2000048601A1 (de) * | 1999-02-16 | 2000-08-24 | Solvay Pharmaceuticals Gmbh | Arzneimittel zur behandlung von bluthochdruck |
| WO2001003699A1 (de) * | 1999-07-13 | 2001-01-18 | Solvay Pharmaceuticals Gmbh | Arzneimittel mit protektiver wirkung gegen oxidativ-toxische und insbesondere gegen kardiotoxische substanzen |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2758771C1 (ru) * | 2018-01-31 | 2021-11-01 | Форту-Фоур ФАРМАЦЕУТИКАЛС Сп. з о.о. | ИНГИБИТОРЫ НЕЙТРАЛЬНОЙ ЭНДОПЕПТИДАЗЫ (НЭП) И РАСТВОРИМОЙ ЭНДОПЕПТИДАЗЫ ЧЕЛОВЕКА (РЭПч) ДЛЯ ПРОФИЛАКТИКИ И ЛЕЧЕНИЯ ГЛАЗНЫХ БОЛЕЗНЕЙ |
Also Published As
| Publication number | Publication date |
|---|---|
| KR100979077B1 (ko) | 2010-08-31 |
| EP1468010A1 (en) | 2004-10-20 |
| US20050038012A1 (en) | 2005-02-17 |
| KR20040089106A (ko) | 2004-10-20 |
| CN1617883A (zh) | 2005-05-18 |
| AU2003206755B2 (en) | 2008-07-17 |
| NO330528B1 (no) | 2011-05-09 |
| JP4384495B2 (ja) | 2009-12-16 |
| IL162645A0 (en) | 2005-11-20 |
| US6998398B2 (en) | 2006-02-14 |
| CN100591689C (zh) | 2010-02-24 |
| HRP20040560A2 (en) | 2004-10-31 |
| BR0306701A (pt) | 2004-12-28 |
| JP2005520809A (ja) | 2005-07-14 |
| RU2004124840A (ru) | 2006-01-20 |
| CA2473447A1 (en) | 2003-07-24 |
| MXPA04006887A (es) | 2004-12-06 |
| PL371511A1 (en) | 2005-06-27 |
| NO20043295L (no) | 2004-08-06 |
| WO2003059939A1 (en) | 2003-07-24 |
| HK1072946A1 (zh) | 2005-09-16 |
| AU2003206755A1 (en) | 2003-07-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8481780B2 (en) | Polymorphs of bromfenac sodium and methods for preparing bromfenac sodium polymorphs | |
| KR100347423B1 (ko) | 구아니딘알킬-1,1-비스포스폰산유도체,이의제조방법및이를함유하는약제 | |
| RU2303041C2 (ru) | Твердые соли бензазепиновых соединений и их применение при получении фармацевтических соединений | |
| EA025438B1 (ru) | КРИСТАЛЛИЧЕСКИЙ КОМПЛЕКС 1-ЦИАНО-2-(4-ЦИКЛОПРОПИЛБЕНЗИЛ)-4-(β-D-ГЛЮКОПИРАНОЗ-1-ИЛ)БЕНЗОЛА, СПОСОБЫ ЕГО ПОЛУЧЕНИЯ И ЕГО ПРИМЕНЕНИЕ ДЛЯ ПРИГОТОВЛЕНИЯ ЛЕКАРСТВЕННЫХ СРЕДСТВ | |
| EP2311794B1 (en) | Polymorphs of bromfenac sodium and methods for preparing bromfenec sodium polymorphs | |
| JP2000506543A (ja) | ４―オキソブタン酸を含有する医薬組成物 | |
| TWI537245B (zh) | 用於治療自體免疫發炎疾病之化合物 | |
| TWI284039B (en) | Solid salts of benzazepine compounds and their use in the preparation of pharmaceutical compounds | |
| HUT75341A (en) | New salts of 2-[(2,6-dichloro-phenyl)-amino]-phenyl-acetoxy-acetic acid with organic bases, pharmaceutical compns. contg. them and process for preparing the said compds. | |
| ZA200405263B (en) | Solid salts benzazepine compounds and their use in the preparation of pharmaceutical compounds. | |
| HK1137993A (en) | Solid salts benzazepine compounds and their use in the preparation of pharmaceuticals compounds | |
| HK1072946B (en) | Solid salts benzazepine compounds and their use in the preparation of pharmaceuticals compounds | |
| JPH024593B2 (enExample) | ||
| HU196211B (en) | Process for producing 1-hydroxy-5-oxo-5h-pindo/3,2-a/phenoxazine-3-carboxylic acid esters and pharmaceuticals comprising the same as active ingredient | |
| JP2018083822A (ja) | ブロムフェナクナトリウムの多形体、及び、ブロムフェナクナトリウム多形体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20120116 |