TW550256B - N-substituted indole-3-glyoxylamides having anti-asthmatic, antiallergic and immunosuppressant/immuno-modulating action - Google Patents

N-substituted indole-3-glyoxylamides having anti-asthmatic, antiallergic and immunosuppressant/immuno-modulating action Download PDF

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TW550256B
TW550256B TW086112985A TW86112985A TW550256B TW 550256 B TW550256 B TW 550256B TW 086112985 A TW086112985 A TW 086112985A TW 86112985 A TW86112985 A TW 86112985A TW 550256 B TW550256 B TW 550256B
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alkyl
substituted
group
furthermore
alkoxy
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TW086112985A
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Guillaume Lebaut
Cecilia Menciu
Bernhard Kutscher
Peter Emig
Stefan Szelenyi
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Asta Pharman Ag
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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D401/14—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 three or more hetero rings

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Transplantation (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)

Description

550256 A8 B8 C8 D8 六'、申請專利乾圍 醯胺 (請先閱脅背面之注意事項再填寫本頁) N —(吡啶一 3_基）一〔1一（2 —氟苄基）吲哚—3 一基〕乙醛醯胺 N— (4-氟苯基）一〔1- (4 —氟苄基）吲哚-3 — 基〕乙醛醯胺 N — (4_硝基苯基）—〔1 一（4_氟苄基）吲哚-3 -基〕乙醛醯胺 N_ (2 —氯基卩比π定_3 -基）—〔1一（4 一氟节基） 吲哚一 3 _基〕乙醛醯胺 N_ (吡啶一 4_基）一（1_苄基吲哚_3 —基）乙醛 醯胺 N _ (吡啶一 4 -基）_〔 1 一（ 3 _吡啶甲基）吲哚一 3 —基〕乙醛醯胺 N_ (4_氟苯基）一〔1 一（2-吡啶甲基）吲哚—3 一基〕乙醛醯胺 N_ (4-氟苯基）一〔1一（3-吡啶甲基）吲哚_3 一基〕乙醛醯胺 經濟部智慧財產局員工消費合作社印製 N —(卩比D定—4 —基）一〔1— (4 —氟< 节基）Π引哄—3 一基〕乙醛醯胺 N_ (卩比卩定一 4 —基）—〔1_ (2 -氟节基）π引哄一 3 一基〕乙醛醯胺 N -(吡啶—2_基）_〔 1_ (4 —氟苄基）吲哚一 3 一基〕乙醛醯胺 Ν — (Π比陡一4 一基）一〔1_ (2 —卩比π定甲基）D弓丨噪一 本姜氏張尺度逋用中國國家標準（CNS ) A4規格（210X297公釐） -4- 550256 A8 B8 C8 D8 六、申請專利範圍 3 —基〕乙醛醯胺 N —(苯基哌嗪一 1—基）— 一（4 —氟苄基）吲哚 經濟部智慧財產局員工消費合作社印製 一 3_基〕乙醛醯胺 N —（吡啶_2_基）一（1—苄基吲哚一 3 —基）乙醛 醯胺 N_ (吡啶一4 —基）—哌嗪—1-基） 〔1 一（4 一氟苄基）吲哚—3 —基〕乙醛醯胺 N —(吡啶一 4 —基一〔1_ (4 —氟苄基）一6 —乙氧 羰基胺基吲哚一3 —基〕乙醛醯胺 N —(卩比D定一4_基）一〔1— (4 一氟节基）一5 —乙 氧羰基胺基吲哚- 3 -基〕乙醛醯胺 N —(耻B定—4_基）—〔1_ (4 —氟节基）—6 —環 戊氧羰基胺基吲哚- 3 -基〕乙醛醯胺 N_ (3，4，5 —三甲氧基苄基）一 N -（烯丙胺基羰 基一 2_甲基丙—1—基）〔1_(4 —氟苄基）吲哚— 3 _基〕乙醛醯胺 N —(卩比d定一4_基）一〔1一（4 一氟辛基）一5 —甲 氧基吲哚一 3 —基〕乙醛醯胺 N -(吡啶一4 —基）-〔1— (4一氟苄基）一 5 —羥 基吲哚一3—基〕乙醛醯胺，及 N —吡啶—4 一基〔1 一（4 —氟苄基）一5 —乙氧羰基 胺甲基吲哚一 3 —基〕乙醛醯胺。 3 .—種對移植及選自牛皮癣、風濕性病症慢性多關 節炎之疾病具有抗氣喘、抗過敏及免疫抑制/免疫調節作 請 先 閲 之 注
I 旁
I 訂
I 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -5- 550256 A8 B8 C8 D8 六、申請專利範圍 用之藥學組成物，含有至少一個如申請專利範圍第1及2 項中任一項之化學式I之化合物，再加上慣用之賦形劑及 /或稀釋劑或是輔助劑。 4 .如申請專利範圍第3項之藥學組成物，其具有肽 基脯氨醯異構酶抑制活性。 5 .如申請專利範圍第3項之藥學組成物，彼係爲藥 片、包衣藥片、膠囊、溶液或安瓿、栓劑、貼藥、可經由 吸入、懸浮液、乳霜及軟膏方式使用之散劑製劑的形態。 6 · —種供製備如申請專利範圍第1及2項中任一項 之化學式I之N -經取代吲哚一 3 -乙醛醯胺類的方法， 其R、 R!、 R2、 R3、 R4及Z具有如申請專利範圍第1 項所述之意義，其特徵爲 a )將如下式IV之吲哚衍生物
經濟部智慧財產局員工消費合作社印製 (其中R3及R4具有上述之意義）加入於一懸浮於質 子性、偶極性質子惰性或非極性有機溶劑之鹼中，再 使之與一帶有如上述定義之R2基的反應化合物反應， 然後令下式V之1 -吲哚衍生物 本紙張尺度適用中國國家標準（CNS ) A4说格（210X297公釐） -6- 550256 A8 B8 C8 D8 申請專利範圍
V R, (其中R2、113及114具有如上述定義）與下式VI之 反應化合物反應 C — Z — Ha 1)
VI (其中Z表示氧’而Ha 1表示鹵素氟、氯、溴或碘 )’接著再與溶於質子惰性或偶極性質子惰性溶劑中 之下式να之一級胺或二級胺反應 Η N R R 1
VH 經濟部智慧財產局員工消費合作社印製
(其中尺及尺1具有上述之定義），如此即可離析化學 式I之目標化合物； 或者 b )在質子惰性或非極性溶劑中令下式JV之吲哚衍生物 R/i 1 ' IV
本纸張尺度逋用中國國家標準（CNS ) Α4規格（210X297公釐） --------------丁______ (請先閲部背面之注意事項再填寫本頁) β 550256 A8 B8 C8 D8 六、申請專利範圍 (其中R3及R_4具有上述定義）與下式yj之反應化合 物反應 (C— Z — Ha 1 ) 2 vi (其中Z表示氧，而Ha 1表示鹵素氟、氯、溴或碘 )’然後再於質子惰性或偶極性質子惰性溶劑中使之 與下式νπ之一級胺或二級胺反應
Η N R R 1 W (其中具有上述之定義），接著在質子性、偶 極性質子惰性或非極性有機溶劑中並在經懸浮之鹼存 在下，令下式VDI之吲哚衍生物 (請先閲·#背面之注意事項再填寫本頁)
經濟部智慧財產局員工消費合作社印製 (其中R、Ri、R2、R3、114及2具有上述定義） 與一帶有如上述定義之R2基的反應化合物反應，如此 即可離析出化學式I之目標化合物。 ^纸張纽適用t關家標準(CNS ) A4規格（210X297公釐） -8
TW086112985A 1996-09-06 1997-09-30 N-substituted indole-3-glyoxylamides having anti-asthmatic, antiallergic and immunosuppressant/immuno-modulating action TW550256B (en)

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DE19636150A DE19636150A1 (de) 1996-09-06 1996-09-06 N-substituierte Indol-3-glyoxylamide mit antiasthmatischer, antiallergischer und immunsuppressiver/immunmodulierender Wirkung

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US (4) US6008231A (zh)
EP (1) EP0931063B3 (zh)
JP (1) JP3296437B2 (zh)
KR (1) KR100516321B1 (zh)
CN (3) CN100376554C (zh)
AR (1) AR008630A1 (zh)
AT (1) ATE342889T1 (zh)
AU (1) AU726521B2 (zh)
BR (1) BR9712808B1 (zh)
CA (1) CA2215013C (zh)
CZ (1) CZ302301B6 (zh)
DE (2) DE19636150A1 (zh)
DK (1) DK0931063T5 (zh)
ES (1) ES2276433T7 (zh)
HK (3) HK1021641A1 (zh)
HU (1) HU227797B1 (zh)
IL (1) IL127798A (zh)
NO (2) NO314725B3 (zh)
NZ (1) NZ334476A (zh)
PT (1) PT931063E (zh)
RU (1) RU2237661C2 (zh)
SK (1) SK285618B6 (zh)
TR (1) TR199900469T2 (zh)
TW (1) TW550256B (zh)
UA (1) UA60312C2 (zh)
WO (1) WO1998009946A1 (zh)
ZA (1) ZA977475B (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109000634B (zh) * 2018-06-04 2022-06-03 上海智蕙林医疗科技有限公司 一种导航对象行进路线的提醒方法和系统

Families Citing this family (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19636150A1 (de) * 1996-09-06 1998-03-12 Asta Medica Ag N-substituierte Indol-3-glyoxylamide mit antiasthmatischer, antiallergischer und immunsuppressiver/immunmodulierender Wirkung
ID27884A (id) * 1998-03-31 2001-05-03 Inst For Pharm Discovery Inc Asam-asam indolealkanoat yang disubstitusikan.
CZ302588B6 (cs) * 1998-04-02 2011-07-27 Ziopharm Oncology, Inc. Použití N-substituovaného indol-3-glyoxylamidu pro výrobu léciva
DE19814838C2 (de) 1998-04-02 2001-01-18 Asta Medica Ag Indolyl-3-glyoxylsäure-Derivate mit Antitumorwirkung
DE19946301A1 (de) 1998-04-02 2001-04-19 Asta Medica Ag Indolyl-3-glyoxylsäure-Derivate mit therapeutisch wertvollen Eigenschaften
DE19818964A1 (de) * 1998-04-28 1999-11-04 Dresden Arzneimittel Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phospodiesterase 4 und Verfahren zu deren Herstellung
ES2262072T3 (es) * 1998-04-28 2006-11-16 Elbion Ag Derivados de indol y su utilizacion como inhibidores de la fosfodiesterasa 4.
DE19917504A1 (de) * 1999-04-17 2000-10-19 Dresden Arzneimittel Verwendung von Hydroxyindolen, die Inhibitoren der Phosphodiesterase 4 sind, zur Therapie chronisch obstruktiver Lungenerkrankungen
EP2193808A1 (en) 1999-08-21 2010-06-09 Nycomed GmbH Synergistic combination
TWI269654B (en) * 1999-09-28 2007-01-01 Baxter Healthcare Sa N-substituted indole-3-glyoxylamide compounds having anti-tumor action
DE19962300A1 (de) * 1999-12-23 2001-06-28 Asta Medica Ag Substituierte N-Benzyl-Indol-3-yl-glyoxylsäure-Derivate mit Antitumorwirkung
DE10022925A1 (de) * 2000-05-11 2001-11-15 Basf Ag Substituierte Indole als PARP-Inhibitoren
DE10037310A1 (de) * 2000-07-28 2002-02-07 Asta Medica Ag Neue Indolderivate und deren Verwendung als Arzneimittel
AU2002323474B2 (en) * 2001-09-13 2006-10-05 Synta Pharmaceuticals Corp 3-glyoxlylamideindoles for treating cancer
US6903104B2 (en) * 2001-12-06 2005-06-07 National Health Research Institutes Indol-3-YL-2-oxoacetamide compounds and methods of use thereof
CN1684685A (zh) * 2002-07-26 2005-10-19 药物研发有限责任公司 取代的吲哚基链烷酸衍生物和含有其的治疗糖尿病并发症用配制剂
US7122674B2 (en) * 2002-08-01 2006-10-17 Elbion Ag Process for preparing high-purity hydroxyindolylglyoxylamides
DE10253426B4 (de) * 2002-11-15 2005-09-22 Elbion Ag Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phosphodiesterase 4 und Verfahren zu deren Herstellung
DE10318611A1 (de) * 2003-04-24 2004-11-11 Elbion Ag 4-, 6- oder 7-Hydroxyindole mit N-Oxidgruppen und deren Verwendung als Therapeutika
DE10318609A1 (de) * 2003-04-24 2004-11-11 Elbion Ag 5-Hydroxyindole mit N-Oxidgruppen und deren Verwendung als Therapeutika
DE10318610A1 (de) 2003-04-24 2004-11-11 Elbion Ag 7-Azaindole und deren Verwendung als Therapeutika
US20050075364A1 (en) * 2003-07-01 2005-04-07 Kap-Sun Yeung Indole, azaindole and related heterocyclic N-substituted piperazine derivatives
US7749999B2 (en) 2003-09-11 2010-07-06 Itherx Pharmaceuticals, Inc. Alpha-ketoamides and derivatives thereof
CA2571710A1 (en) 2004-06-24 2006-11-02 Nicholas Valiante Small molecule immunopotentiators and assays for their detection
DE102004031538A1 (de) * 2004-06-29 2006-02-09 Baxter International Inc., Deerfield Pharmazeutische Darreichungsform zur oralen Verabreichung eines schwerlöslichen Wirkstoffs, Verfahren zu deren Herstellung und Kit
CA2587276A1 (en) * 2004-11-08 2006-05-18 Baxter International Inc. Nanoparticulate compositions of tubulin inhibitor compounds
US20060100432A1 (en) * 2004-11-09 2006-05-11 Matiskella John D Crystalline materials of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione
US20060100209A1 (en) * 2004-11-09 2006-05-11 Chong-Hui Gu Formulations of 1-(4-benzoyl-piperazin-1-yl)-2-[4-methoxy-7-(3-methyl-[1,2,4]triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-ethane-1,2-dione
WO2006073973A2 (en) 2004-12-31 2006-07-13 Reddy Us Therapeutics, Inc. Novel benzylamine derivatives as cetp inhibitors
US8604055B2 (en) 2004-12-31 2013-12-10 Dr. Reddy's Laboratories Ltd. Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors
JP2006247963A (ja) * 2005-03-09 2006-09-21 Oji Paper Co Ltd インクジェット記録用シート
EP2363128B1 (en) * 2005-03-11 2016-02-17 Vertex Pharmaceuticals Incorporated Indole modulators of ATP-binding cassette transporters
US7404381B2 (en) 2005-04-29 2008-07-29 Tendix Development, Llc Radial impulse engine, pump, and compressor systems, and associated methods of operation
US20060280787A1 (en) * 2005-06-14 2006-12-14 Baxter International Inc. Pharmaceutical formulation of the tubulin inhibitor indibulin for oral administration with improved pharmacokinetic properties, and process for the manufacture thereof
US7598380B2 (en) * 2005-08-03 2009-10-06 Bristol-Myers Squibb Company Method of preparation of azaindole derivatives
ITMI20051999A1 (it) * 2005-10-21 2007-04-22 Eratech S R L Formulazioni inalatorie di farmaci in fora di polvere secca per somministrazione come tale o con nebulizzatore e dotate di elevata erogabilita' respirabilita' e stabilita'
US7851476B2 (en) * 2005-12-14 2010-12-14 Bristol-Myers Squibb Company Crystalline forms of 1-benzoyl-4-[2-[4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-YL)-1-[(phosphonooxy)methyl]-1H-pyrrolo[2,3-C]pyridin-3-YL]-1,2-dioxoethyl]-piperazine
US7807671B2 (en) * 2006-04-25 2010-10-05 Bristol-Myers Squibb Company Diketo-piperazine and piperidine derivatives as antiviral agents
CN102764440A (zh) 2006-07-05 2012-11-07 奈科明有限责任公司 用于治疗炎症性肺部疾病的HMG-CoA还原酶抑制剂与磷酸二酯酶4抑制剂的组合
EP2610244A1 (en) * 2006-08-07 2013-07-03 Ironwood Pharmaceuticals, Inc. Indole compounds
EP2066619A2 (en) * 2006-11-02 2009-06-10 Arete Therapeutics, INC. Soluble epoxide hydrolase inhibitors
EP2091532A1 (en) * 2006-11-28 2009-08-26 Ziopharm Oncology, Inc. Use of indolyl-3-glyoxylic acid derivatives including indibulin, alone or in combination with further agents for treating cancer
NZ789295A (en) 2009-04-29 2024-02-23 Amarin Pharmaceuticals Ie Ltd Pharmaceutical compositions comprising epa and a cardiovascular agent and methods of using the same
AR084433A1 (es) 2010-12-22 2013-05-15 Ironwood Pharmaceuticals Inc Inhibidores de la faah y composiciones farmaceuticas que los contienen
CN103827105B (zh) 2011-08-18 2016-08-17 雷迪博士实验室有限公司 作为胆固醇酯转移蛋白(cetp)抑制剂的取代的杂环胺化合物
CN103958511A (zh) 2011-09-27 2014-07-30 雷迪博士实验室有限公司 作为胆固醇酯转移蛋白(CETP)抑制剂用于治疗动脉粥样硬化的5-苄基氨基甲基-6-氨基吡唑并[3,4-b]吡啶衍生物
EP3165224A1 (en) 2015-11-09 2017-05-10 Albert-Ludwigs-Universität Freiburg Use of pde4 inhibitors for the prophylaxis and/or therapy of dyslipoproteinaemia and related disorders
WO2017089347A1 (en) 2015-11-25 2017-06-01 Inserm (Institut National De La Sante Et De La Recherche Medicale) Methods and pharmaceutical compositions for the treatment of braf inhibitor resistant melanomas

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB797258A (en) * 1955-04-11 1958-06-25 Upjohn Co 3-substituted indoles
GB944443A (zh) * 1959-09-25 1900-01-01
GB1028812A (en) * 1962-08-28 1966-05-11 Ici Ltd Indole derivatives
GB1089071A (en) * 1964-02-28 1967-11-01 Merck & Co Inc Indole derivatives
US3686213A (en) * 1970-08-28 1972-08-22 American Cyanamid Co Substituted aminoethyl indoles
FR2689888B1 (fr) * 1992-04-10 1994-06-10 Rhone Poulenc Rorer Sa Nouveaux derives de perhydroisoindole, leur preparation et les compositions pharmaceutiques qui les contiennent.
CZ82295A3 (en) * 1994-04-01 1995-12-13 Lilly Co Eli Derivative of 1h-indole-3-glyoxylamide and a pharmaceutical composition containing thereof
DE19636150A1 (de) * 1996-09-06 1998-03-12 Asta Medica Ag N-substituierte Indol-3-glyoxylamide mit antiasthmatischer, antiallergischer und immunsuppressiver/immunmodulierender Wirkung
DE19946301A1 (de) * 1998-04-02 2001-04-19 Asta Medica Ag Indolyl-3-glyoxylsäure-Derivate mit therapeutisch wertvollen Eigenschaften
US7205299B2 (en) * 2003-06-05 2007-04-17 Zentaris Gmbh Indole derivatives having an apoptosis-inducing effect

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109000634B (zh) * 2018-06-04 2022-06-03 上海智蕙林医疗科技有限公司 一种导航对象行进路线的提醒方法和系统

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