CZ369099A3 - Způsob výroby 2-aryl-3-aryl-5-halogenpyridinů - Google Patents
Způsob výroby 2-aryl-3-aryl-5-halogenpyridinů Download PDFInfo
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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Description
Absorbent oxidu uhličitého
Oblast techniky
Vynález se týká nového strukturálního typu absorbentu oxidu uhličitého na bázi derivátů aminů.
Dosavadní stav techniky
Oxid uhličitý lze obecně jímat hydroxidy alkalických kovů a alkalických zemin, hydroxidy kvartémích amoniových baží, popřípadě ethanolaminy, přičemž je jejich použití limitováno pro jejich značnou hydrofilitu vodným prostředím, ve kterém pak vykazují extrémní bazicitu. Navíc, vazba oxidu uhličitého po jeho reakci s těmito činidly je velmi pevná a její štěpení je možno provést pouze poměrně silnými kyselinami. Kromě toho jsou tato činidla značně dráždivá a toxická, nelze je snadno regenerovat a jsou nerozpustná ve většině organických rozpouštědel.
Podstata vynálezu
Uvedené nedostatky odstraňuje absorbent oxidu uhličitého na bázi derivátů aminů dle obecného vzorce (I)
Ri-CH-(CH2)n-COO(CH2)mR2
Y (I) kde Rj je H nebo Ci až C3 alkyl, n = 2 až 14, m = 3 až 15, R2 = NH2, -CH3, Y = H, NH2.
Látky tohoto typu reverzibilně a kvantitativně vážou oxid uhličitý za vzniku příslušných amoniových solí karbamových kyselin, po jejichž rozpuštění v organických rozpouštědlech je oxid uhličitý opět uvolněn, je možno ho stanovit běžnými analytickými postupy včetně scintilačních metod, je-li radioaktivně označen nebo je možno jej jinak použít, přičemž je možno absorbent odpařením roztoku regenerovat. Absorbent se vpraví do prostoru, ve kterém má být oxid uhličitý jímán, uvolněn nebo stanoven, popřípadě před prostor, do kterého nemá vniknout, in substantia nebo nanesený na vhodném nosiči. Reakcí aminoskupiny absorbentu s oxidem uhličitým v tomto prostoru vzniká amoniová sůl odpovídající karbamové kyseliny, která je za normálních podmínek stabilní a rozpustná v organických rozpouštědlech. Jejím rozpouštěním a zahřátím v rozmezí teplot 15 °C až teplota varu rozpouštědla, dochází k rozkladu na původní sloučeninu a volný oxid uhličitý, což umožní jeho snadné stanovení nebo jiné využití. Odstraněním rozpouštědla je absorbent regenerován a je možno ho použít znovu.
Absorbenty na bázi aminů obecného vzorce I jsou vysoce reaktivní vůči volnému oxidu uhličitému i při nízkých koncentracích řádově v pmolech. Jsou rozpustné v lipofilních rozpouštědlech včetně uhlovodíků, což mimo jiné umožňuje levnější stanovení radioaktivního oxidu uhličitého při použití hydrofobních scintilačních roztoků. Díky snadnému uvolňování oxidu uhličitého z absorbentu lze tento absorbent použít jako transportní formu radioaktivního oxidu uhličitého.
Absorbent umožňuje vyčerpání i stopových množství oxidu uhličitého z daného prostoru, zamezení možnosti oxidu uhličitému do prostoru vniknout, popřípadě jej v uzavřeném prostoru v čas potřeby uvolnit a pak stanovit či jinak využít.
Absorbent je málo bazický, rozpustný v organických rozpouštědlech, nedráždivý, netoxický a není embryotoxický.
Vynález je dále objasněn na příkladech pro vedení,jimiž ovšem jeho rozsah není omezen ani vyčerpán.
Příklady provedení
Příklad 1:
Stanovení aktivity dekarboxylas
Mikrozkumavka se 4,5 . 1O'10 mol substrátu dekarboxylasy (karboxylová kyselina značená na karboxylu 14C) a se supematantem živočišné tkáně (centrifugovaném při 20 000 g) je vložena do scintilační lahvičky na jejímž dně je umístěn filtrační papír (0,7 cm) napuštěný decylesterem 6-aminohexanové kyseliny. Enzymová reakce je ukončena přídavkem 2.104 mol kyseliny citrónové a vzorek inkubován 60 minut při 37 °C. Filtrační papír s absorbentem přenesen do mikrozkumavky a přidán 1 ml hydrofobního scintilačního roztoku. Oxid uhličitý je stanoven α,β-spektrometrem. Množství absorbovaného oxidu uhličitého 14C bylo 4,45. 10’10 molů.
Příklad 2:
Stanovení aktivity omithindekarboxylasy
Mikrozkumavka s 4,5 . IO'10 mol hydrochloridu D,L-1-14C omithinu a se supematantem živočišné tkáně (20 000 g) je vložena do scintilační lahvičky na jejímž dně je umístěn 6-amino-l-hexylester nonanové kyseliny. Enzymová reakce je ukončena 2.10'4 mol kyseliny citrónové a vzorek inkubován 60 minut při 37 °C. Mikrozkumavka je odstraněna a do scintilační lahvičky je nalito 5 ml hydrofobního scintilačního roztoku. Oxid uhličitý byl stanoven α,β-spektrometrem v množství 4,45 . 10'10mol.
Příklad 3.
Příprava síranu bamatého
Roztok chloridu bamatého ve vodě prosté oxidu uhličitého vpravíme do baňky opatřené přikapávací nálevkou a nad něj umístíme na porézní destičku ze slinutého skla (fritu) s naneseným oktylesterem 6-aminoheptanové kyseliny k zamezení přístupu atmosferického oxidu uhličitého. Po 30 minutách přidáme 5% hmotn. přebytek roztoku síranu sodného. Vysrážený síran bamatý odfiltrujeme. Přítomnost uhličitanů nebyla prokázána.
Příklad 4
Příprava radioaktivně značené kyseliny 2,4,6-trihydroxybenzoové
Mmol 5-aminopentylesteru děkanové kyseliny s naadsorbovaným 14CO2 je vloženo do ampule s roztokem 4 mmol sodné soli floroglucinu v 6 ml vody. Ampule je zatavena a zahřívána 4 hodiny na 120 °C. Po ochlazení je obsah okyselen konc. kyselinou chorovodíkovou na pH 1 a krystaly při 0 °C odfiltrovány. Vzniklá kyselina 2,4,6-trihydroxybenzoová (14COOH) může být překrystalována z vody.
Příklad 5
Regenerace použitého absorbentu
0,2 g nasyceného absorbentu - amoniové soli karbamové kyseliny vzniklé z oktylesteru 8-aminooktanové kyseliny navázáním oxidu uhličitého je rozpuštěno ve 20 ml chloroformu. Směs byla zahřáta 5 minut na 50 °C a vakuově zahuštěna. Infračervené spektrum získané olej ovité látky bylo totožné s výchozím oktylesterem 8aminooktanové kyseliny získaným za stejných podmínek.
Průmyslová využitelnost
Absorbent oxidu uhličitého je využitelný v laboratorním i průmyslovém měřítku tam, kde je nutno měřit množství oxidu uhličitého včetně možnosti uchování referenčního vzorku, neboť vzniklá sloučenina je stabilní za laboratorní teploty několik let, vyčerpat oxid uhličitý z daného prostoru, zamezit vzniku oxidu uhličitého do daného prostoru, nebo naopak v daném prostoru oxid uhličitý v případě potřeby uvolnit.
Claims (4)
- Patentové nároky1. Absorbent oxidu uhličitého na bázi derivátů aminů obecného vzorce IRi-CH-(CH2)n-COO(CH2)mR2Y (I) kde Rj je H nebo Q - C3 alkyl, n = 2-14, m = 3-15, R2 = NH2, -CH3, Y = H, NH2.
- 2. Absorbent podle nároku 1 v y z n a ě u j í c í se t i m , že se používá in substantia
- 3. Absorbent podle nároku 1 v y z n a č u j í c i se t í m, že se používá nanesený na vhodném nosiči.
- 4. Způsob regenerace absorbentu podle nároku 1 až 3 v y z n a č u j í c í se t í m, že se použitý absorbent rozpustí v organickém rozpouštědle vybraném ze skupiny alkoholů, halogenovaných rozpouštědel a aromatických uhlovodíků při teplotě 15 °C až teplotě varu rozpouštědla a rozpouštědlo se vakuově odpaří.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4564297P | 1997-04-18 | 1997-04-18 | |
| GBGB9709686.1A GB9709686D0 (en) | 1997-05-13 | 1997-05-13 | Process for making 2-aryl-3-aryl-5-halo pyridines useful as cox-2 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ369099A3 true CZ369099A3 (cs) | 2000-04-12 |
| CZ293246B6 CZ293246B6 (cs) | 2004-03-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ19993690A CZ293246B6 (cs) | 1997-04-18 | 1998-04-14 | Způsob výroby 2-aryl-3-aryl-5-halogenpyridinů |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0975596B1 (cs) |
| JP (1) | JP3300369B2 (cs) |
| KR (1) | KR20010006546A (cs) |
| CN (1) | CN1182117C (cs) |
| AT (1) | ATE270275T1 (cs) |
| AU (1) | AU729730B2 (cs) |
| BR (1) | BR9808923B1 (cs) |
| CA (1) | CA2287482C (cs) |
| CZ (1) | CZ293246B6 (cs) |
| DE (1) | DE69824839T2 (cs) |
| EA (1) | EA002190B1 (cs) |
| ES (1) | ES2223128T3 (cs) |
| HR (1) | HRP980206B1 (cs) |
| HU (1) | HU226999B1 (cs) |
| NZ (1) | NZ500390A (cs) |
| PL (1) | PL190265B1 (cs) |
| RS (1) | RS49901B (cs) |
| SK (1) | SK285037B6 (cs) |
| TW (1) | TW492959B (cs) |
| UA (1) | UA66792C2 (cs) |
| WO (1) | WO1998047871A1 (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR015938A1 (es) | 1997-09-25 | 2001-05-30 | Merck Sharp & Dohme | Procedimiento para preparar diaril piridinas utiles como inhibidores cox-2 y compuesto intermediario |
| KR100446324B1 (ko) * | 1999-01-14 | 2004-08-30 | 론자 아게 | 1-(6-메틸피리딘-3-일)-2-[4-(메틸술포닐)페닐]에타논 및이의 제조 방법 |
| DK1159270T3 (da) * | 1999-01-14 | 2004-02-23 | Lonza Ag | Fremgangsmåde til fremstilling af 1-(6-methylpyridin-3-yl)-2-[(4-(methylsulfonyl)phenyl]ethanon |
| US6566527B1 (en) | 1999-07-27 | 2003-05-20 | Merck & Co., Inc. | Process for preparing 1-(6-methylpyridin-3-yl)-2-[4-methylsulphonyl)-phenyl]ethanone |
| ES2207536T3 (es) * | 1999-07-27 | 2004-06-01 | Lonza Ag | Procedimiento para preparar 1-(6-metilpiridin-3-il)-2-((4-metilsulfonil)fenil)etanona. |
| CO5261556A1 (es) | 1999-12-08 | 2003-03-31 | Pharmacia Corp | Composiciones inhibidoras de ciclooxigenasa-2 que tiene rapido acceso de efecto terapeutico |
| JP2003523958A (ja) | 1999-12-23 | 2003-08-12 | ニトロメド インコーポレーテッド | ニトロソ化およびニトロシル化されたシクロオキシゲナーゼ−２の阻害剤、組成物ならびに使用法 |
| JP2001261647A (ja) * | 2000-03-22 | 2001-09-26 | Sankio Chemical Co Ltd | ピリジン誘導体の製造方法 |
| NZ524252A (en) | 2000-07-20 | 2004-03-26 | Lauras As | Cox-2 inhibitors for treating HIV and AIDS |
| AR038957A1 (es) | 2001-08-15 | 2005-02-02 | Pharmacia Corp | Terapia de combinacion para el tratamiento del cancer |
| JP2005535642A (ja) | 2002-06-28 | 2005-11-24 | ニトロメッド インコーポレーティッド | オキシムおよび／またはヒドラゾンを含有するニトロソ化および／またはニトロシル化シクロオキシゲナーゼ−２選択的阻害剤、組成物、および使用方法 |
| WO2011158250A1 (en) * | 2010-06-16 | 2011-12-22 | Glenmark Generics Limited | Process for preparation of 2, 3-diaryl-5-substituted pyridines and their intermediates |
| RU2591848C2 (ru) * | 2010-11-15 | 2016-07-20 | Вирдев Интермидиетс Пвт. Лтд. | Способ получения селективного ингибитора циклооксигеназы-2 |
| CN103204803A (zh) | 2012-01-13 | 2013-07-17 | 阿尔弗雷德·E·蒂芬巴赫尔有限责任两合公司 | 用于合成依托考昔的方法 |
| WO2014114352A1 (en) * | 2013-01-25 | 2014-07-31 | Synthon Bv | Process for making etoricoxib |
| WO2015036550A1 (en) | 2013-09-13 | 2015-03-19 | Synthon B.V. | Process for making etoricoxib |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CH561202A5 (cs) * | 1971-05-10 | 1975-04-30 | Ciba Geigy Ag | |
| US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5686470A (en) * | 1995-02-10 | 1997-11-11 | Weier; Richard M. | 2, 3-substituted pyridines for the treatment of inflammation |
| JP3267300B2 (ja) * | 1995-02-13 | 2002-03-18 | ジー．ディー．サール アンド カンパニー | 炎症の治療のための置換イソオキサゾール |
| US5643933A (en) * | 1995-06-02 | 1997-07-01 | G. D. Searle & Co. | Substituted sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
| US5677318A (en) * | 1996-07-11 | 1997-10-14 | Merck Frosst Canada, Inc. | Diphenyl-1,2-3-thiadiazoles as anti-inflammatory agents |
| SI0912518T1 (en) * | 1996-07-18 | 2003-12-31 | Merck Frosst Canada & Co. | Substituted pyridines as selective cyclooxygenase-2 inhibitors |
-
1998
- 1998-04-09 TW TW087105349A patent/TW492959B/zh not_active IP Right Cessation
- 1998-04-14 WO PCT/US1998/008312 patent/WO1998047871A1/en not_active Ceased
- 1998-04-14 BR BRPI9808923-4A patent/BR9808923B1/pt not_active IP Right Cessation
- 1998-04-14 AU AU72571/98A patent/AU729730B2/en not_active Ceased
- 1998-04-14 KR KR1019997009636A patent/KR20010006546A/ko not_active Withdrawn
- 1998-04-14 UA UA99116266A patent/UA66792C2/uk unknown
- 1998-04-14 AT AT98919881T patent/ATE270275T1/de not_active IP Right Cessation
- 1998-04-14 NZ NZ500390A patent/NZ500390A/en unknown
- 1998-04-14 JP JP54636798A patent/JP3300369B2/ja not_active Expired - Fee Related
- 1998-04-14 EP EP98919881A patent/EP0975596B1/en not_active Expired - Lifetime
- 1998-04-14 EA EA199900948A patent/EA002190B1/ru not_active IP Right Cessation
- 1998-04-14 SK SK1436-99A patent/SK285037B6/sk not_active IP Right Cessation
- 1998-04-14 DE DE69824839T patent/DE69824839T2/de not_active Expired - Lifetime
- 1998-04-14 PL PL98336298A patent/PL190265B1/pl not_active IP Right Cessation
- 1998-04-14 RS YUP-536/99A patent/RS49901B/sr unknown
- 1998-04-14 CZ CZ19993690A patent/CZ293246B6/cs not_active IP Right Cessation
- 1998-04-14 ES ES98919881T patent/ES2223128T3/es not_active Expired - Lifetime
- 1998-04-14 HU HU0003155A patent/HU226999B1/hu not_active IP Right Cessation
- 1998-04-14 CN CNB988061864A patent/CN1182117C/zh not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20120414 |