HUP0301576A2 - A Neutrofilek IL-8 által indukált kemotaxisának gátlására alkalmazható amidok, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények - Google Patents
A Neutrofilek IL-8 által indukált kemotaxisának gátlására alkalmazható amidok, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítményekInfo
- Publication number
- HUP0301576A2 HUP0301576A2 HU0301576A HUP0301576A HUP0301576A2 HU P0301576 A2 HUP0301576 A2 HU P0301576A2 HU 0301576 A HU0301576 A HU 0301576A HU P0301576 A HUP0301576 A HU P0301576A HU P0301576 A2 HUP0301576 A2 HU P0301576A2
- Authority
- HU
- Hungary
- Prior art keywords
- group
- general formula
- imidazolyl
- formula
- alkyl
- Prior art date
Links
- 230000035605 chemotaxis Effects 0.000 title abstract 2
- 210000000440 neutrophil Anatomy 0.000 title abstract 2
- 150000001408 amides Chemical class 0.000 title 1
- 230000005764 inhibitory process Effects 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- -1 1-imidazolyl Chemical group 0.000 abstract 16
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 2
- 229910052717 sulfur Chemical group 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 abstract 1
- 102000004890 Interleukin-8 Human genes 0.000 abstract 1
- 108090001007 Interleukin-8 Proteins 0.000 abstract 1
- 229910003827 NRaRb Inorganic materials 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 abstract 1
- 125000000539 amino acid group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 abstract 1
- 229940096397 interleukin-8 Drugs 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
Classifications
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- C07D213/02—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
- 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C07C233/51—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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Abstract
A találmány tárgya az (I) általános képletű 2-aril-propionamid- (R)-enantiomerek és ezek gyógyászatilag elfogadható sói a neutrofilekinterleukin-8 által indukált kemotaxisának gátlására valóalkalmazásra. Az (I) általános képletben Aril jelentése adott esetbenhelyettesített arilcsoport; R jelentése hidrogénatom vagy alkil-, allil-, propargilcsoport vagy-CH2COOH vagy -(CH2)2-COOH képletű csoport; R' jelentése - aminosavmaradék, amely egy vagy több karboxicsoporttal helyettesített alkil-,alkenil- vagy cikloalkil vagy fenilalkil-csoportot tartalmaz; -aminosav maradék, amely egy vagy több karboxicsoporttal és az oxigén-és kénatom közül választott heteroatommal helyettesített alkil-,alkenil-, cikloalkil- vagy fenilalkil-csoportot tartalmaz; - -CH2-CH2X- (CH2-CH2O)nR általános képletű csoport, ahol R jelentése afenti; n értéke 0 és 5 közötti egész szám, míg X jelentése oxigén vagykén; - (R) vagy (S)-CH(CH3)-CH2-O-CH2-CH2-OH képletű csoport, - -ORáltalános képletű csoport, ahol R jelentése a fenti; - (III) általánosképletű csoport, ahol ahol F jelentése 2-(1-metil-pirrolidil), 2-piridil, 4-piridil, 1-imidazolil, 4-imidazolil, 1-metil-4-imidazolil,1-metil-5-imidazolil vagy -NRaRb általános képletű csoport, ahol Ra ésRb jelentése egymással azonos vagy különböző, és lehet 1-6 szénatomosalkil- vagy -(CH2)m-OH általános képletű hidroxialkilcsoport, ahol mértéke 2 vagy 3, vagy Ra és Rb a nitrogénatommal együtt, amelyhezkapcsolódnak, egy 3-7 tagú (IV) általános képletű csoportot alkot,ahol Y jelentése egyes kötés, -CH2-, O, S vagy NRc általános képletűcsoport, ahol Rc jelentése hidrogénatom, alkilcsoport, -(CH2)mOHáltalános képletű hidroxialkilcsoport és/vagy egy -(CH2)m'Ar'általános képletű csoport, ahol Ar' jelentése aril-, heteroaril-,cikloalifás és/vagy heterocikloalifás csoport, m' értéke 0-tól 3-igterjedő egész szám és p és q jelentése egymástól függetlenül 1-től 3-ig terjedő egész szám; heteroarilcsoport, amelyet a következőcsoportok közül választanak: 2-piridil- vagy 4-piridil-, 2-pirimidinil- vagy 4-pirimidinil-, 2-pirazinil-, 5-metil-2-pirazinil;3-1,2,4-tiazinil; 3-1,2,4-tiazolil; 3-1-benzil-1,2,4-tiazolil-, 2-1,3-tiazolidinil-, 2-1,3-tiazolil-, 1,3-oxazolil-, 3-izoxazolil-, 4-dihidro-3-oxo-izoxazolil-, 5-metil-izoxazol-4-il, 2-imidazolil-, 4-imidazolil-5-karboxamid és 2-imidazolil-4,5-dikarbonitril-, 5-indanil-, 5-indazolil-, 7-aza-indol-3-il-, 2- vagy 3- vagy 4-kinolinilcsoport. A találmány kiterjed a vegyületek előállítására ésezeket tartalmazó gyógyszerkészítményekre is. Ó
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT2000MI000227A IT1317826B1 (it) | 2000-02-11 | 2000-02-11 | Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8. |
PCT/EP2001/001285 WO2001058852A2 (en) | 2000-02-11 | 2001-02-06 | (r)-2-aryl-propionamides, useful in the inhibition of il-8-induced chemiotaxis of neutrophils |
Publications (3)
Publication Number | Publication Date |
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HUP0301576A2 true HUP0301576A2 (hu) | 2003-11-28 |
HUP0301576A3 HUP0301576A3 (en) | 2004-10-28 |
HU229447B1 HU229447B1 (en) | 2013-12-30 |
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Application Number | Title | Priority Date | Filing Date |
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HU0301576A HU229447B1 (en) | 2000-02-11 | 2001-02-06 | Amides useful in the inhibition of il-8-induced chemotaxis of neutrophils |
Country Status (28)
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US (1) | US7705050B2 (hu) |
EP (1) | EP1255726B1 (hu) |
JP (1) | JP4937479B2 (hu) |
KR (1) | KR100884417B1 (hu) |
CN (1) | CN100513386C (hu) |
AT (1) | ATE448195T1 (hu) |
AU (2) | AU2001244125B2 (hu) |
BR (2) | BR0108152A (hu) |
CA (1) | CA2396937C (hu) |
CY (1) | CY1109780T1 (hu) |
CZ (1) | CZ302945B6 (hu) |
DE (1) | DE60140429D1 (hu) |
DK (1) | DK1255726T3 (hu) |
EE (1) | EE05284B1 (hu) |
ES (1) | ES2336301T3 (hu) |
HK (1) | HK1062675A1 (hu) |
HU (1) | HU229447B1 (hu) |
IL (1) | IL150523A0 (hu) |
IT (1) | IT1317826B1 (hu) |
MX (1) | MXPA02007714A (hu) |
NO (1) | NO331460B1 (hu) |
NZ (1) | NZ519925A (hu) |
PL (1) | PL207126B1 (hu) |
PT (1) | PT1255726E (hu) |
RU (1) | RU2273630C2 (hu) |
SI (1) | SI1255726T1 (hu) |
SK (1) | SK287224B6 (hu) |
WO (1) | WO2001058852A2 (hu) |
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IT1318466B1 (it) * | 2000-04-14 | 2003-08-25 | Dompe Spa | Ammidi di acidi r-2-(amminoaril)-propionici, utili nella prevenzionedell'attivazione leucocitaria. |
TWI243164B (en) | 2001-02-13 | 2005-11-11 | Aventis Pharma Gmbh | Acylated indanyl amines and their use as pharmaceuticals |
ITMI20010395A1 (it) | 2001-02-27 | 2002-08-27 | Dompe Spa | Omega-amminoalchilammidi di acidi r-2-aril-propionici come inibitori della chemiotassi di cellule polimorfonucleate e mononucleate |
ITMI20012025A1 (it) * | 2001-09-28 | 2003-03-28 | Dompe Spa | Sali di ammonio quaternari di omega-amminoalchilammidi di acidi r 2-aril-propionici e composizioni farmaceutiche che li contengono |
ITMI20012434A1 (it) * | 2001-11-20 | 2003-05-20 | Dompe Spa | Acidi 2-aril-propionici e composizioni farmaceutiche che li contengono |
ES2312834T3 (es) * | 2002-12-10 | 2009-03-01 | Dompe S.P.A. | Arilcetonas quirales en el tratamiento de enfermedades inflamatorias dependientes de neutrofilos. |
JP5208411B2 (ja) | 2003-02-06 | 2013-06-12 | ドムペ・ファ.ル.マ・ソチエタ・ペル・アツィオーニ | 2−アリール−酢酸、その誘導体、及びそれらを含有する医薬組成物 |
EP1457485A1 (en) * | 2003-03-14 | 2004-09-15 | Dompé S.P.A. | Sulfonic acids, their derivatives and pharmaceutical compositions containing them |
RU2375346C2 (ru) | 2003-09-25 | 2009-12-10 | ДОМПЕ ФА.Р.МА С.п.А. | Амидины и их производные и содержащие их фармацевтические композиции |
RS51109B (sr) * | 2004-03-23 | 2010-10-31 | Dompe S.P.A. | Derivati 2-fenilpropionske kiseline i farmaceutske smeše koje ih sadrže |
CA2589495C (en) * | 2004-12-15 | 2013-10-01 | Dompe Pha.R.Ma. S.P.A. | 2-arylpropionic acid derivatives and pharmaceutical compositions containing them |
EP1676834A1 (en) | 2004-12-30 | 2006-07-05 | Sanofi-Aventis Deutschland GmbH | Fused bicyclic carboxamide derivates for use as CXCR2 inhibitors in the treatment of inflammation |
US20090131441A1 (en) * | 2005-01-25 | 2009-05-21 | Dompe Phar.R.Ma S.P.A. | Metabolites Of 2-Arylpropionic Acid Derivatives And Pharmaceutical Compositions Containing Them |
CN101448784B (zh) | 2006-05-18 | 2012-07-04 | 冬姆佩股份公司 | (2r)-2-[(4-磺酰基)氨基苯基]丙酰胺及含有它们的药物组合物 |
JP5237938B2 (ja) | 2006-06-28 | 2013-07-17 | サノフイ | 新規なcxcr2阻害剤 |
JP5352454B2 (ja) | 2006-06-28 | 2013-11-27 | サノフイ | Cxcr2アンンタゴニスト |
WO2008000407A1 (en) | 2006-06-28 | 2008-01-03 | Sanofi-Aventis | Inhibitors of cxcr2 |
WO2008000410A1 (en) | 2006-06-30 | 2008-01-03 | Sanofi-Aventis | Cxcr2 inhibitors |
US20090238763A1 (en) | 2006-07-09 | 2009-09-24 | Chongxi Yu | High penetration compositions and uses thereof |
US20090221703A1 (en) | 2006-07-09 | 2009-09-03 | Chongxi Yu | High penetration composition and uses thereof |
WO2008020270A1 (en) * | 2006-08-15 | 2008-02-21 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of aryl- and heteroarylpropionic acids with very fast skin penetration rate |
CN103772259B (zh) * | 2006-08-08 | 2016-08-31 | 于崇曦 | 具有快速皮肤穿透速度的带正电荷的芳基和杂芳基乙酸类前药 |
CN103772258B (zh) * | 2006-08-08 | 2016-09-28 | 于崇曦 | 具有快速皮肤穿透速度的带正电荷的芳基和杂芳基乙酸类前药 |
EP2990402A1 (en) * | 2006-08-08 | 2016-03-02 | Techfields Biochem Co. Ltd | Positively charged water-soluble prodrugs of aryl- and heteroarylacetic acids with very fast skin penetration rate |
CN101687792B (zh) | 2007-06-04 | 2016-03-02 | 于崇曦 | 具有快速皮肤和生物膜穿透速度的非甾体抗炎药的前药及其医药用途 |
CA2700880C (en) * | 2007-10-08 | 2016-03-08 | Bongkoch Tarnchompoo | Antimalarial compounds with flexible side-chains |
US8217064B2 (en) | 2007-12-20 | 2012-07-10 | Envivo Pharmaceuticals, Inc. | Tetrasubstituted benzenes |
EP2166006A1 (en) * | 2008-09-18 | 2010-03-24 | Dompe' S.P.A. | 2-aryl-propionic acids and derivatives and pharmaceutical compositions containing them |
RU2630577C2 (ru) | 2008-12-04 | 2017-09-11 | Чунси ЮЙ | Композиции интенсивного проникновения и их применение |
US8815271B2 (en) * | 2010-11-03 | 2014-08-26 | Dow Agrosciences, Llc. | Pesticidal compositions and processes related thereto |
CN103159674A (zh) * | 2013-04-03 | 2013-06-19 | 苏州安诺生物医药技术有限公司 | 2-苯烷酰胺类化合物及其制备方法、药物组合物和用途 |
US11850220B2 (en) * | 2020-05-19 | 2023-12-26 | Augusta University Research Institute, Inc. | Synthesis of ibuprofen hybrid conjugates as anti-inflammatory and analgesic agents |
KR20230093944A (ko) | 2021-12-20 | 2023-06-27 | 주식회사 우아한형제들 | 자율이동장치의 최적 주행 경로를 결정하기 위한 방법 및 이를 수행하는 컴퓨팅 시스템 |
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JPS54141754A (en) * | 1978-04-26 | 1979-11-05 | Takayuki Shioiri | Manufacture of 22*33benzoylphenyl*propionic acid |
IT1193955B (it) * | 1980-07-22 | 1988-08-31 | Real Di Alberto Reiner S A S | Derivati ammidici dell'acido p-isobutilfenilpropionico, procedimento per la loro preparazione e relative composizioni farmaceutici |
IT1203605B (it) * | 1985-04-18 | 1989-02-15 | Alfa Chem Ital | Processo per la risoluzione ottica di miscigli racemi di acidi e naftilpropionici |
GB8719886D0 (en) * | 1987-08-22 | 1987-09-30 | British Petroleum Co Plc | Carboxylic acid esters/acids |
JPH0791216B2 (ja) * | 1988-10-10 | 1995-10-04 | 日本石油化学株式会社 | α−(3−(1−フエニルエチル)フェニル)プロピオン酸 |
WO1994003209A1 (en) * | 1992-07-29 | 1994-02-17 | Merck & Co., Inc. | Dexibuprofen/antacid/simethicone combinations |
EP0618223A3 (en) * | 1993-03-08 | 1996-06-12 | Sandoz Ltd | Peptides, the release of Interleukin 1-Bêta, useful as anti-inflammatory agents. |
JPH07149646A (ja) * | 1993-11-29 | 1995-06-13 | Asahi Chem Ind Co Ltd | ケミカルメディエーター遊離抑制剤 |
US6040321A (en) * | 1997-11-12 | 2000-03-21 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
MY153569A (en) | 1998-01-20 | 2015-02-27 | Mitsubishi Tanabe Pharma Corp | Inhibitors of ?4 mediated cell adhesion |
WO2000002903A1 (en) * | 1998-07-10 | 2000-01-20 | Cytel Corporation | Cs-1 peptidomimetics, compositions and methods of using the same |
GB9823871D0 (en) | 1998-10-30 | 1998-12-23 | Pharmacia & Upjohn Spa | 2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents |
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2000
- 2000-02-11 IT IT2000MI000227A patent/IT1317826B1/it active
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- 2001-02-06 SK SK1141-2002A patent/SK287224B6/sk not_active IP Right Cessation
- 2001-02-06 EP EP01916976A patent/EP1255726B1/en not_active Expired - Lifetime
- 2001-02-06 HU HU0301576A patent/HU229447B1/hu unknown
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- 2001-02-06 EE EEP200200441A patent/EE05284B1/xx not_active IP Right Cessation
- 2001-02-06 AU AU2001244125A patent/AU2001244125B2/en not_active Ceased
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- 2001-02-06 RU RU2002124136/04A patent/RU2273630C2/ru not_active IP Right Cessation
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