RU2005104954A - Кристаллические твердые формы (2s,5z)-2-амино-7-(этанимидоиламино)-2-метилгепт-5-еноевой кислоты - Google Patents
Кристаллические твердые формы (2s,5z)-2-амино-7-(этанимидоиламино)-2-метилгепт-5-еноевой кислоты Download PDFInfo
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- RU2005104954A RU2005104954A RU2005104954/04A RU2005104954A RU2005104954A RU 2005104954 A RU2005104954 A RU 2005104954A RU 2005104954/04 A RU2005104954/04 A RU 2005104954/04A RU 2005104954 A RU2005104954 A RU 2005104954A RU 2005104954 A RU2005104954 A RU 2005104954A
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- Prior art keywords
- amino
- iminoethyl
- acid
- methyl
- hydrochloride
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- 239000002253 acid Substances 0.000 title 1
- 239000007787 solid Substances 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 10
- XRYVIWRHMIMIDT-ATPLWMGHSA-N (z,2s)-2-amino-7-(1-aminoethylideneamino)-2-methylhept-5-enoic acid Chemical compound CC(=N)NC\C=C/CC[C@](C)(N)C(O)=O XRYVIWRHMIMIDT-ATPLWMGHSA-N 0.000 claims 5
- BNJMLKUXIDPCSH-MEDGODRVSA-N (z,2s)-2-amino-7-(1-aminoethylideneamino)-2-methylhept-5-enoic acid;hydrochloride Chemical compound Cl.CC(=N)NC\C=C/CC[C@](C)(N)C(O)=O BNJMLKUXIDPCSH-MEDGODRVSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- XRYVIWRHMIMIDT-UHFFFAOYSA-N 2-amino-7-(1-aminoethylideneamino)-2-methylhept-5-enoic acid Chemical compound CC(=N)NCC=CCCC(C)(N)C(O)=O XRYVIWRHMIMIDT-UHFFFAOYSA-N 0.000 claims 2
- 229940123921 Nitric oxide synthase inhibitor Drugs 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 239000000236 nitric oxide synthase inhibitor Substances 0.000 claims 2
- 229940127240 opiate Drugs 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000003200 Adenoma Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
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- 201000004624 Dermatitis Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 208000017228 Gastrointestinal motility disease Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000001953 Hypotension Diseases 0.000 claims 1
- 206010062016 Immunosuppression Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 238000001237 Raman spectrum Methods 0.000 claims 1
- 206010042496 Sunburn Diseases 0.000 claims 1
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 229940035676 analgesics Drugs 0.000 claims 1
- 239000000730 antalgic agent Substances 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 229940049706 benzodiazepine Drugs 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 230000004927 fusion Effects 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 208000007565 gingivitis Diseases 0.000 claims 1
- 230000036543 hypotension Effects 0.000 claims 1
- 210000000987 immune system Anatomy 0.000 claims 1
- 230000001506 immunosuppresive effect Effects 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000007774 longterm Effects 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 230000002981 neuropathic effect Effects 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 230000003040 nociceptive effect Effects 0.000 claims 1
- 238000010899 nucleation Methods 0.000 claims 1
- 230000004792 oxidative damage Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000003093 somatogenic effect Effects 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/14—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to acyclic carbon atoms
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Claims (8)
1. Кристаллическая форма 2-амино-7-(этанимидоиламино)-2-метилгепт-5-еноевой кислоты.
2. Кристаллическая форма 2-амино-7-(этанимидоиламино)-2-метилгепт-5-еноевой кислоты, отличающаяся, по крайней мере, одним физическим параметром, выбранным из группы, включающей порошковую рентгенограмму в соответствии с фиг.3, спектр Рамана в соответствии с фиг.6, температуру плавления 224°С и теплоту плавления 147 Дж/г-1.
3. Соединение формулы (I)
являющееся 1,5 гидрохлоридом (2S,5Z)-2-амино-7-(этанимидоиламино)-2-метилгепт-5-еноевой кислоты или его физиологически функциональным производным.
4. Фармацевтическая композиция, содержащая эффективное количество 1,5 гидрохлорида (2S,5Z)-2-амино-7-(этанимидоиламино)-2-метилгепт-5-еноевой кислоты в сочетании с фармацевтически приемлемым носителем.
5. Способ профилактики или лечения клинического состояния у млекопитающего, такого, как человек, при котором показан ингибитор синтазы окиси азота, который включает введение терапевтически эффективного количества соединения по п.1.
6. Способ по п.5, в котором указанное клиническое состояние выбирают из группы, состоящей из боли, включая соматогенную (либо ноцицептивную, либо невропатическую), острую и хроническую; толерантности к опиатам у пациентов, которым необходим длительный прием опиатных аналгетиков; толерантности к бензодиазепину у пациентов, принимающих бензолдиазепины; других видов привыкания, например к никотину, и расстройств питания; системной гипотензии, связанной с септическим и/или токсическим шоком; глазных заболеваний; системной красной волчанки (СКВ); гломерулонефрита, рестеноза, воспалительных осложнений при вирусных заболеваниях; острого респираторного дистресс-синдрома (ОРДС); вызванных окислителями повреждений легких; осложнений при IL2 терапии; кахексии; иммунодепрессии; расстройств моторики желудочно-кишечного тракта; солнечных ожогов; экземы; псориаза; гингивита; панкреатита; повреждений желудочно-кишечного тракта вследствие инфекций; кистозного фиброза; лечения дисфункций иммунной системы; полипозных аденом; контроля роста опухолей; и бронхита.
7. Применение соединения по п.1 для получения лекарственного средства для профилактики или лечения клинического состояния, при котором показан ингибитор синтазы окиси азота.
8.Способ получения кристаллического 1,5 гидрохлорида (2S,5Z)-2-амино-7-(этанимидоиламино)-2-метилгепт-5-еноевой кислоты, включающий стадии
(а) получения некристаллической формы (2S,5Z)-2-амино-2-метил-7-[(1-иминоэтил)амино]-5-гептеновой кислоты;
(b) необязательного добавления хлористоводородной кислоты до тех пор, пока (2S,5Z)-2-амино-2-метил-7-[(1-иминоэтил)амино]-5-гептеновая кислота не достигнет эквивалента 1,5 HCl; или
(с) необязательного регулирования концентрации хлористоводородной кислоты подходящим основанием до тех пор, пока (2S,5Z)-2-амино-2-метил-7-[(1-иминоэтил)амино]-5-гептеновая кислота не достигнет эквивалента 1,5 HCl; или
(d) необязательного удаления других противоионов соли из (2S,5Z)-2-амино-2-метил-7-[(1-иминоэтил)амино]-5-гептеновой кислоты и добавления хлористоводородной кислоты до тех пор, пока (2S,5Z)-2-амино-2-метил-7-[(1-иминоэтил)амино]-5-гептеновая кислота не достигнет эквивалента 1,5 гидрохлорида;
(е) необязательного затравливания 1,5 гидрохлорида (2S,5Z)-2-амино-2-метил-7-[(1-иминоэтил)амино]-5-гептеновой кислоты, полученного из кристаллического 1,5 гидрохлорида (2S,5Z)-2-амино-2-метил-7-[(1-иминоэтил)амино]-5-гептеновой кислоты; и
(f) необязательного добавления растворителя.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40552602P | 2002-08-23 | 2002-08-23 | |
| US60/405,526 | 2002-08-23 | ||
| US60/405526 | 2002-08-23 |
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| Publication Number | Publication Date |
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| RU2005104954A true RU2005104954A (ru) | 2005-07-20 |
| RU2314290C2 RU2314290C2 (ru) | 2008-01-10 |
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| RU2005104954/04A RU2314290C2 (ru) | 2002-08-23 | 2003-08-22 | Кристаллическая твердая форма 1,5 гидрохлорида (2s,5z)-2-амино-7-(этанимидоиламино)-2-метилгепт-5-еноевой кислоты, способ ее получения, фармацевтическая композиция на ее основе |
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| US (1) | US6998503B2 (ru) |
| EP (1) | EP1534668B1 (ru) |
| JP (1) | JP4708024B2 (ru) |
| KR (1) | KR100893647B1 (ru) |
| CN (1) | CN100588647C (ru) |
| AR (1) | AR041038A1 (ru) |
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| GB9127376D0 (en) | 1991-12-24 | 1992-02-19 | Wellcome Found | Amidino derivatives |
| DK0751930T3 (da) | 1994-03-24 | 2000-04-17 | Searle & Co | Amidinoderivater anvendelige som nitrogenoxid-synthase-inhibitorer |
| US5684008A (en) | 1994-11-09 | 1997-11-04 | G. D. Searle & Co. | Aminotetrazole derivatives useful as nitric oxide synthase inhibitors |
| US5945408A (en) | 1996-03-06 | 1999-08-31 | G.D. Searle & Co. | Hydroxyanidino derivatives useful as nitric oxide synthase inhibitors |
| MY131964A (en) * | 2000-09-15 | 2007-09-28 | Pharmacia Corp | 2-amino-2-alkyl-5 heptenoic and heptynoic acid derivatives useful as nitric oxide synthase inhibitors |
| GB0031179D0 (en) * | 2000-12-21 | 2001-01-31 | Glaxo Group Ltd | Nitric oxide synthase inhibitors |
| US7012098B2 (en) * | 2001-03-23 | 2006-03-14 | Pharmacia Corporation | Inhibitors of inducible nitric oxide synthase for chemoprevention and treatment of cancers |
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Also Published As
| Publication number | Publication date |
|---|---|
| RU2314290C2 (ru) | 2008-01-10 |
| CA2494583A1 (en) | 2004-03-04 |
| JP4708024B2 (ja) | 2011-06-22 |
| AU2003258327B2 (en) | 2009-05-21 |
| KR20050058443A (ko) | 2005-06-16 |
| TWI340133B (en) | 2011-04-11 |
| NO20050609L (no) | 2005-03-21 |
| HK1078562A1 (en) | 2006-03-17 |
| ZA200501134B (en) | 2006-10-25 |
| WO2004018412A1 (en) | 2004-03-04 |
| ES2384969T3 (es) | 2012-07-16 |
| CA2494583C (en) | 2010-02-02 |
| CN100588647C (zh) | 2010-02-10 |
| ATE556047T1 (de) | 2012-05-15 |
| EP1534668A1 (en) | 2005-06-01 |
| US6998503B2 (en) | 2006-02-14 |
| IL166599A0 (en) | 2006-01-15 |
| KR100893647B1 (ko) | 2009-04-17 |
| PL375557A1 (en) | 2005-11-28 |
| CN1678572A (zh) | 2005-10-05 |
| NZ538184A (en) | 2008-02-29 |
| IL166599A (en) | 2010-12-30 |
| MXPA05001708A (es) | 2005-04-19 |
| BR0313752A (pt) | 2005-06-21 |
| AU2003258327A1 (en) | 2004-03-11 |
| JP2005536541A (ja) | 2005-12-02 |
| US20040132822A1 (en) | 2004-07-08 |
| TW200413291A (en) | 2004-08-01 |
| AR041038A1 (es) | 2005-04-27 |
| EP1534668B1 (en) | 2012-05-02 |
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