EA006245B1 - Гидрохлорид 4-[4-(2-пирролилкарбонил)-1-пиперазинил]-3-трифторметилбензоилгуанидина - Google Patents
Гидрохлорид 4-[4-(2-пирролилкарбонил)-1-пиперазинил]-3-трифторметилбензоилгуанидина Download PDFInfo
- Publication number
- EA006245B1 EA006245B1 EA200300771A EA200300771A EA006245B1 EA 006245 B1 EA006245 B1 EA 006245B1 EA 200300771 A EA200300771 A EA 200300771A EA 200300771 A EA200300771 A EA 200300771A EA 006245 B1 EA006245 B1 EA 006245B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- piperazinyl
- pyrrolylcarbonyl
- compound
- diseases
- Prior art date
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- UFVMVHAWZDUFMJ-UHFFFAOYSA-N n-(diaminomethylidene)-4-[4-(1h-pyrrole-2-carbonyl)piperazin-1-yl]-3-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC(C(=O)NC(=N)N)=CC=C1N1CCN(C(=O)C=2NC=CC=2)CC1 UFVMVHAWZDUFMJ-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 11
- 230000004060 metabolic process Effects 0.000 claims description 4
- 230000001413 cellular effect Effects 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims description 2
- 150000004682 monohydrates Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 3
- 239000013543 active substance Substances 0.000 description 15
- 229940079593 drug Drugs 0.000 description 11
- 210000002216 heart Anatomy 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 208000028867 ischemia Diseases 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 206010002383 Angina Pectoris Diseases 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 206010020880 Hypertrophy Diseases 0.000 description 4
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- 210000004556 brain Anatomy 0.000 description 4
- 208000020832 chronic kidney disease Diseases 0.000 description 4
- 208000022831 chronic renal failure syndrome Diseases 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- SRRHGTUDJFMQIV-UHFFFAOYSA-N n-(diaminomethylidene)-4-[4-(1h-pyrrole-2-carbonyl)piperazin-1-yl]-3-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC(C(=O)N=C(N)N)=CC=C1N1CCN(C(=O)C=2NC=CC=2)CC1 SRRHGTUDJFMQIV-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
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- 229940088679 drug related substance Drugs 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical class NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 230000010410 reperfusion Effects 0.000 description 3
- 238000002054 transplantation Methods 0.000 description 3
- 208000009304 Acute Kidney Injury Diseases 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
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- 206010021143 Hypoxia Diseases 0.000 description 2
- 208000033626 Renal failure acute Diseases 0.000 description 2
- 206010063897 Renal ischaemia Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000007718 Stable Angina Diseases 0.000 description 2
- 206010043626 Thrombosis mesenteric vessel Diseases 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000012907 medicinal substance Substances 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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
- 206010061216 Infarction Diseases 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 108010023197 Streptokinase Proteins 0.000 description 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
- 206010053648 Vascular occlusion Diseases 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
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- 210000004413 cardiac myocyte Anatomy 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
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- 239000008120 corn starch Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
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- 239000002274 desiccant Substances 0.000 description 1
- 208000033679 diabetic kidney disease Diseases 0.000 description 1
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- 239000003527 fibrinolytic agent Substances 0.000 description 1
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- 239000012458 free base Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
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- 230000002427 irreversible effect Effects 0.000 description 1
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- 210000003734 kidney Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- ZCUAIZGPONHJHP-UHFFFAOYSA-N n-(diaminomethylidene)-4-[4-(1h-pyrrole-2-carbonyl)piperazin-1-yl]-3-(trifluoromethyl)benzamide;hydrate;hydrochloride Chemical compound O.Cl.FC(F)(F)C1=CC(C(=O)NC(=N)N)=CC=C1N1CCN(C(=O)C=2NC=CC=2)CC1 ZCUAIZGPONHJHP-UHFFFAOYSA-N 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000004088 pulmonary circulation Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960005202 streptokinase Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 208000021331 vascular occlusion disease Diseases 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
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- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
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- A61K9/2022—Organic macromolecular compounds
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Surgery (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10106970A DE10106970A1 (de) | 2001-02-15 | 2001-02-15 | Neues Benzoylguanidinsalz |
| PCT/EP2002/001535 WO2002064563A1 (de) | 2001-02-15 | 2002-02-14 | Neues benzoylguanidinsalz |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200300771A1 EA200300771A1 (ru) | 2004-02-26 |
| EA006245B1 true EA006245B1 (ru) | 2005-10-27 |
Family
ID=7674094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200300771A EA006245B1 (ru) | 2001-02-15 | 2002-02-14 | Гидрохлорид 4-[4-(2-пирролилкарбонил)-1-пиперазинил]-3-трифторметилбензоилгуанидина |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US20080025919A1 (enExample) |
| EP (1) | EP1362030B1 (enExample) |
| JP (3) | JP4408626B2 (enExample) |
| KR (1) | KR100862176B1 (enExample) |
| CN (1) | CN1222510C (enExample) |
| AT (1) | ATE553078T1 (enExample) |
| AU (1) | AU2002250939B2 (enExample) |
| BG (1) | BG66330B1 (enExample) |
| BR (1) | BR0207867A (enExample) |
| CA (1) | CA2434829C (enExample) |
| CY (1) | CY1112878T1 (enExample) |
| CZ (1) | CZ303277B6 (enExample) |
| DE (1) | DE10106970A1 (enExample) |
| DK (1) | DK1362030T3 (enExample) |
| EA (1) | EA006245B1 (enExample) |
| EC (1) | ECSP034708A (enExample) |
| EE (1) | EE200300393A (enExample) |
| ES (1) | ES2385472T3 (enExample) |
| HR (1) | HRP20030653B1 (enExample) |
| HU (1) | HU230035B1 (enExample) |
| IL (1) | IL156934A (enExample) |
| NO (1) | NO20033299D0 (enExample) |
| NZ (1) | NZ528081A (enExample) |
| PL (1) | PL213300B1 (enExample) |
| PT (1) | PT1362030E (enExample) |
| RS (1) | RS52014B (enExample) |
| SI (1) | SI1362030T1 (enExample) |
| SK (1) | SK287830B6 (enExample) |
| UA (1) | UA74625C2 (enExample) |
| WO (1) | WO2002064563A1 (enExample) |
| ZA (1) | ZA200305365B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10106970A1 (de) * | 2001-02-15 | 2002-08-29 | Boehringer Ingelheim Pharma | Neues Benzoylguanidinsalz |
| US6982256B2 (en) | 2001-09-07 | 2006-01-03 | Boehringer Ingelheim Pharma Kg | Tolerance of 4-(4-(2-pyrrolylcarbonyl)-1-piperazinyl)-3-trifluoromethyl-benzoylguanidine in intravenous administration |
| DE10144030A1 (de) * | 2001-09-07 | 2003-03-27 | Boehringer Ingelheim Pharma | Verbesserung der lokalen Verträglichkeit bei intravenöser Verabreichung von 4-(4-(2-Pyrrolylcarbonyl-1-piperazinyl)-3-trifluormethyl-benzoylguanidin |
| US20110118262A1 (en) * | 2008-07-08 | 2011-05-19 | Boehringer Ingelheim International Gmbh | Pyrrolidinyl and Piperidinyl Compounds Useful as NHE-1 Inhibitiors |
| US10405746B2 (en) * | 2014-04-14 | 2019-09-10 | The University Of Memphis Research Foundation | Wireless analog passive sensors |
| US12369831B1 (en) | 2018-04-30 | 2025-07-29 | Bashir I. Morshed | Apparatus and method to capture body signals with conjugate coils and paired coils |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19601303A1 (de) * | 1996-01-16 | 1997-07-17 | Boehringer Ingelheim Kg | Neuartige Benzoylguanidin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Herstellung von Arzneimitteln |
| DE19843489B4 (de) * | 1998-09-22 | 2006-12-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Benzoylguanidin-Abkömmlinge mit vorteilhaften Eigenschaften, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Herstellung von Arzneimitteln, sowie diese enthaltende pharmazeutische Zubereitung |
| US6323207B1 (en) * | 1998-09-22 | 2001-11-27 | Boehringer Ingelheim Pharma Kg | Benzoylguanidine derivatives |
| US6730678B2 (en) * | 2001-02-15 | 2004-05-04 | Boehringer Ingelheim Pharma Kg | Benzoylguanidine salt and hydrates thereof |
| DE10106970A1 (de) * | 2001-02-15 | 2002-08-29 | Boehringer Ingelheim Pharma | Neues Benzoylguanidinsalz |
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2001
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
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