WO2005123671A1 - Dérivé du pyrrole - Google Patents

Dérivé du pyrrole Download PDF

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Publication number
WO2005123671A1
WO2005123671A1 PCT/JP2005/011343 JP2005011343W WO2005123671A1 WO 2005123671 A1 WO2005123671 A1 WO 2005123671A1 JP 2005011343 W JP2005011343 W JP 2005011343W WO 2005123671 A1 WO2005123671 A1 WO 2005123671A1
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Prior art keywords
ano
benzoi
group
caboad
atom
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PCT/JP2005/011343
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English (en)
Japanese (ja)
Inventor
Hiroki Umemiya
Tetsuo Takayama
Hideaki Amada
Fumiyasu Shiozawa
Masakazu Sato
Tetsuya Yabuuchi
Hironori Katakai
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Taisho Pharmaceutical Co., Ltd.
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Publication of WO2005123671A1 publication Critical patent/WO2005123671A1/fr

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    • 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
    • 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
    • A61P17/04—Antipruritics
    • 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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
    • C07D403/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/02—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing not further condensed quinolizine ring systems

Definitions

  • 0001 relates to a compound which inhibits nitrogen and a salt thereof.
  • 002-enzyme is a gene that controls the growth and differentiation of cells, and its normal activation has been suggested to be involved.
  • too many elements have been discovered, which are classified into structural, cytoplasmic, and septa types.
  • Sun conductors (4), 5-anorazo conductors (5), and the like are known, but they are not disclosed having a clear structure.
  • the purpose of the present invention is to provide a drug for abortion, such as an atopic dermatitis or breath, which is unreactive in organ transplantation.
  • C represents an alkyne group, and represents hydrogen atom, oxygen atom, gene,
  • the compound represented by the above formula wherein 2 is a hydrogen atom is a pharmaceutically acceptable salt thereof.
  • the compound represented by the above formula wherein is a hydrogen atom is a pharmaceutically acceptable salt thereof.
  • the picones represented by the formulas described in 5 to 4 are therapeutic drugs for immunity and algae containing a pharmaceutically acceptable salt thereof as an active ingredient.
  • Inhibition of ck which is involved in the normal activity of immune cells, is useful for the treatment of animals such as atopic dermatitis, breath, etc.
  • Aki group means, for example, meth, thi, pupi, isoppi, thi, isothi, eti, seti, pliers, isopenti neopenti and thi groups. It is a meth group.
  • 30 aki means a cyclic aki group having 3 or more atomic atoms or a polycyclic aki group, for example, cuppi, cuti, cuppenti, ku, cuti, quochi, Examples include a biocide and an dunk group, and a dunk group is preferable.
  • Zero alkay means a straight-branched alkanoyl group having 2 or more atoms, and examples thereof include thi, ppio,, iso,, and octay groups, and preferably a thi group.
  • C 0 ano means a straight-chain ano group having a few atoms, such as methano, thiano, pupiano, isopropylamine, thiano. , Isothiano, e-thiano, pentiano, and thiano groups.
  • C 0 ano refers to an ano group in which several straight-chained aki groups are converted into two groups, such as methano, methiano, thiano, and tipia. And ppiano groups, with preference given to methano, thiano, zipiano, and dithianosopiano groups.
  • 0026 is a group having at least one oxygen atom or nitrogen atom and having a bond with 3 to 8 quacan atoms or atoms, such as di, di, di, di, ,,,,,,,, And di groups are preferable, and a di, di, di,, di, non, and oxy group are preferable.
  • 0027 means C6 space, hidden C6 space, ano C6 space, C space space, C space space, C100 space, C space space.
  • Pella and 26 methino groups are preferred, with preference given to methidyl, methidyl, methipellar, and benzyl pertoxy.
  • Aquine is a straight-branched alkyne group with 6 atoms
  • chin methine, methine, methine, methine, methine, methine, methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine, methine methine It is.
  • Oki C6 akim means a form in which an oxygen atom and a C6 akim group are combined, and examples thereof include oktin, oktin, and okppine group.
  • the term "akio" means a form in which an akine and an oxygen atom are combined, and examples thereof include a quinoki, a methinoquino, a methinoquino, a chinoki, a ppioki, and a 22-methyl pioki group.
  • C 2 aciano refers to a complex form of an alkyne atom, for example,
  • Examples thereof include a cyano, a methylthio, a methylthio, a cyano, a propiano, and a 22-methylpiperano group.
  • Examples of the gene include a hydrogen atom, a chlorine atom, and a hydrogen atom, and a hydrogen atom, and a hydrogen atom, a chlorine atom, and a hydrogen atom are preferable.
  • the aki that has been exchanged with the four genes is the hydrogen atom on it
  • ibi 4 represents a C 4 aki group in which a hydrogen atom thereon has been replaced by four genes.
  • ibis, ibis, ibis and ibis are preferred, with ibis being preferred.
  • Saturated means that it contains at least one oxygen atom and at least one elementary atom.
  • () Ride b can be produced by reacting a conductor a with tetradran, ton, or the like, or with soppine, tothane, N-methyl, or the like.
  • C can be manufactured. C can also be produced by applying methane to b.
  • G CHNH (, G is a hydrogen atom, 4 toki)
  • e can be produced by reacting with an atom represented by RCOCHB, such as potassium carbonate, cesium carbonate, or sodium hydrogencarbonate, such as ton or tetradran. it can.
  • RCOCHB an atom represented by RCOCHB, such as potassium carbonate, cesium carbonate, or sodium hydrogencarbonate, such as ton or tetradran. it can.
  • Compound h reacts with, or does not react with, or exists in, sodium or methoxide, such as methane sulphone, tonic acid, or reacts compound 9 with radium carbon, radium hydroxide, such as tetradran or methano.
  • Compound h can be produced by a hydrogenation method such as
  • (2 2) 2a can be obtained by hydrolysis of 2a.
  • 3a which is a group represented by 005, is converted to a rosin drug such as tetras-dran
  • a compound 3b is produced by adding a drug such as bokeh and reacting with a compound represented by RH (where R and R are hydrogen atoms and genes, respectively, as defined above). Can be.
  • step (53) 3b can be reacted with methic acid or methionine to form compound 3c.
  • RH (where, R is a hydrogen atom and a gene except from the above definition)
  • X represents a group, and X represents a gene.
  • 3c can be produced by reacting the alkylates 3a represented by).
  • (4) 4b can be produced by reacting 4a, which is a thiol group, with iron, salt, or the like, such as methano, isopno, or methioform.
  • X (where X and X represent a gene and is a C-aki group) is obtained by reacting an acylated compound represented by X.
  • 5 54 d can be manufactured. Also, 4d can be produced by using an aldehyde represented by the formula C (where is the same as the above definition) instead of the formula bark as a base agent such as Sodiu or Sodium Atoki. 006 (4 4) 4b is a mixture of (3 methyl methane propyl) 3 tide, benzoto azo, etc.
  • [0063] 4e can be produced by reacting the represented product.
  • 14 X represents a gene. 4f can be produced by reacting the alkylates represented by ()).
  • 5b which is a toki group, is treated with a bonoid such as methane or 2-octane to produce 5b.
  • the medicament containing the compound of the present invention as an active ingredient can be administered systemically and topically, orally, subcutaneously, muscle, intravenously, or via the skin.
  • the dose for an adult is between ⁇ and OO mg kg, which can be administered in several doses.
  • the mixture was washed with te, washed (, saturated saline), dried (granium sulfate), filtered and concentrated.
  • the colorless 939 was obtained by treatment with the obtained lizard color (Xanchi 955).
  • tetranothium hydride (2749, 5 mmo) was added, and the mixture was heated and flowed. The mixture was returned to a warm temperature, discharged with a tube, washed (a saturated saline solution), dried (aqueous sodium sulfate), filtered and concentrated. The colorless .5 was obtained by washing with the obtained lizard color.
  • Hydrogen 2 (4) H 3 (5 289 2 96 mmo) e-dano (m) calcium hydroxide (7393 mmo) was added, and the mixture was heated and flowed for 5.5 minutes. The mixture was returned to a warm temperature, discharged with a tube, washed (, saturated saline), dried (granium sulfate), filtered and concentrated. Torn lizard
  • the colorless compound 4.2 was obtained by performing the reaction in (h). 2 3 to 2 °
  • Tan (349, 3 mmo) and potassium carbonate (722 m9, 5.24 mmo) were added in that order, and the mixture was treated at room temperature. Water and copper were added, and the mixture was extracted, washed (, saturated saline), dried (granium sulfate), filtered and concentrated.
  • the colorless compound (799) was obtained by reconstitution (thixane) with the obtained lizard color (h).
  • Tano (3 m) hydroxide (2293 mmo) of an H 3 bot (79, 3 ⁇ O mo) was added, and the mixture was heated and flown for 4 hours. The mixture was returned to a warm temperature, discharged with a tube, washed (, saturated saline), dried (granium sulfate), filtered and concentrated. By re-solidifying with the obtained lizard color, the yellow .29 was obtained.
  • Tan (49, 3 ⁇ mmo) and potassium carbonate (O 9, 7.34 mmo) were added to, and the mixture was allowed to stand at room temperature for 23 hours. Water and potassium were added, and the mixture was extracted, washed (, saturated saline), dried (grain water sulfate), filtered and concentrated.
  • a colorless compound (987m9) was obtained by recrystallization (thixane) with a lizard color (h).
  • Tonone (5 629 23 gmmo) was added at room temperature. Water and potassium were added, and the mixture was washed, washed (with saturated saline), dried (granium hydroxide), filtered and concentrated. Torn lizard
  • the mixture was returned to a warm temperature, discharged with a tube, washed (, saturated saline), dried (granium sulfate), filtered and concentrated.
  • the colorless compound (66) was obtained by using the obtained lizard color (thixane) and treating the obtained product with hexane.
  • Tonone (332567 mmo) and potassium carbonate (975942 gmmo) were added in that order, and the mixture was cooled to room temperature.
  • Tonone (28.9 gmmo) was added at room temperature. 2 more
  • Tonone (289 gmmo) was treated with 6 at room temperature. Further, 2 (26 o) tonone (4 789 24 mo) was added, and the mixture was cooled to room temperature. Water and potassium were added to the mixture, and the mixture was extracted, washed (, saturated saline), dried (aqueous sodium sulfate), filtered, and concentrated.
  • the cover was recombined (Tixane) with N Kage Karak NH Kage NH DM0200 (Akisha), developed siloxane 2 and then 9 to obtain a colorless compound (263).
  • N-Kage-Kara-Ku NH-Kage-NH-DM020 (a formula company), developed thixane 4 and then kuhomemethano 9 to form a yellow color by re-consolidation (methano siloxane).
  • the compound (3 mg) was obtained by washing with Chichome 5).
  • the product is made of lizard, and is recrystallized from hexane.
  • the product was obtained by using ano 2 toki 24 (2 toki) tan in place of ano 2 toki 2 (4) tan in accordance with the specifications of 4 (2 toki H pi 3 carbon).
  • the mixture was added with water and water, and the mixture was extracted (, saturated saline), dried (aqueous sodium sulfate), filtered and concentrated.
  • the compound (8) was obtained by reconstitution (Kuhomoxane).
  • a compound was obtained by using ano2toki2 (3to4) tan instead of ano2to2 (4to) tan, and using 26 benzobenide instead of benzide.
  • Figure 8 shows the physical properties of the substance.
  • k25 and ATP2051 were added to a 96-ng ample and incubated at room temperature. After stopping the reaction by adding 10 phosphorus 200, the whole amount of the reaction was transferred to titanium (MAPHNB50), and the reaction was carried out at 0 M 2001.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Transplantation (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Dérivé du pyrrole représenté par la formule générale (1) : (1) (dans laquelle R1 représente un hydrogène ou un alkyle en C1-4 ; R2 représente un alkyle en C1-10, un cycloalkyle en C3-10, un méthylènedioxyphényle, un 1,2-éthylènedioxyphényle, un 1,3-propylènedioxyphényle, etc. ; R3 et R4 sont identiques ou différents et chacun représente un hydrogène, un halogéno, un alkyle en C1-6 ou un alcoxy en C1-6 ; et R5 représente un hydrogène, un halogéno, un nitro, un amino, un hydroxy, un alkyle en C1-6, un alcoxy en C1-6, etc.) ou un sel acceptable du point de vue pharmaceutique du dérivé. Les composés inhibent l'activité enzymatique de la LcK, laquelle participe à l'activation anormale de cellules immunocompétentes et sont utiles pour des réactions de rejet dans une greffe d'organes ou des maladies immunes/allergiques telles que la dermite atopique et l'asthme.
PCT/JP2005/011343 2004-06-22 2005-06-21 Dérivé du pyrrole WO2005123671A1 (fr)

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JP2004-183894 2004-06-22
JP2004183894 2004-06-22

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WO2005123671A1 true WO2005123671A1 (fr) 2005-12-29

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008105408A1 (fr) 2007-02-26 2008-09-04 Santen Pharmaceutical Co., Ltd. Nouveau dérivé de pyrrole ayant un groupe uréide et un groupe aminocarbonyle comme substituants
JP2009536617A (ja) * 2006-04-11 2009-10-15 バーテックス ファーマシューティカルズ インコーポレイテッド タンパク質キナーゼの阻害剤として有用なチアゾール、イミダゾール、およびピラゾール
WO2010024226A1 (fr) * 2008-08-25 2010-03-04 参天製薬株式会社 Agent prophylactique ou thérapeutique utilisé dans les maladies osseuses/articulaires comprenant, pour principe actif, un dérivé pyrrole contenant un groupe uréide, un groupe aminocarbonyle et un groupe phényle substitué comme substituants
WO2010024227A1 (fr) 2008-08-25 2010-03-04 参天製薬株式会社 Nouveau dérivé de pyrrole ayant, en tant que substituants, un groupe uréide, un groupe aminocarbonyle et un groupe bicyclique qui peut avoir un substituant
WO2011041461A3 (fr) * 2009-10-01 2011-08-25 Amira Pharmaceuticals, Inc. Composés polycycliques utiles en tant qu'antagonistes du récepteur de l'acide lysophosphatidique
US8217066B2 (en) 2009-10-01 2012-07-10 Amira Pharmaceuticals, Inc. Compounds as lysophosphatidic acid receptor antagonists
US8541587B2 (en) 2011-04-05 2013-09-24 Amira Pharmaceuticals, Inc. Lysophosphatidic acid receptor antagonists
US9145354B2 (en) 2011-11-01 2015-09-29 Astex Therapeutics Limited Pharmaceutical compounds
WO2015101670A3 (fr) * 2014-01-03 2015-12-03 Elexopharm Gmbh Inhibiteurs des 17bêta-hydroxystéroïde déshydrogénases de type 1 et 2
US10532996B2 (en) 2011-05-12 2020-01-14 Proteostasis Therapeutics, Inc. Proteostasis regulators

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11511755A (ja) * 1996-05-30 1999-10-12 エフ・ホフマン―ラ ロシュ アーゲー 新規ピロール誘導体

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11511755A (ja) * 1996-05-30 1999-10-12 エフ・ホフマン―ラ ロシュ アーゲー 新規ピロール誘導体

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CAMPAIGNE E. ET AL: "Synthesis of some 1-methyl-3-alkoxy-5-arylpirrolecarboxylic acids and derivatives.", JOURNAL OF HETEROCYCLIC CHEMISTRY., vol. 12, no. 1, 1975, pages 67 - 74, XP002991365 *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009536617A (ja) * 2006-04-11 2009-10-15 バーテックス ファーマシューティカルズ インコーポレイテッド タンパク質キナーゼの阻害剤として有用なチアゾール、イミダゾール、およびピラゾール
RU2485101C2 (ru) * 2007-02-26 2013-06-20 Сантен Фармасьютикал Ко., Лтд. Новое производное пиррола, имеющее в качестве заместителей уреидную и аминокарбонильную группу
US7977371B2 (en) 2007-02-26 2011-07-12 Santen Pharmaceutical Co., Ltd. Pyrrole derivative having ureido group and aminocarbonyl group as substituents
WO2008105408A1 (fr) 2007-02-26 2008-09-04 Santen Pharmaceutical Co., Ltd. Nouveau dérivé de pyrrole ayant un groupe uréide et un groupe aminocarbonyle comme substituants
WO2010024226A1 (fr) * 2008-08-25 2010-03-04 参天製薬株式会社 Agent prophylactique ou thérapeutique utilisé dans les maladies osseuses/articulaires comprenant, pour principe actif, un dérivé pyrrole contenant un groupe uréide, un groupe aminocarbonyle et un groupe phényle substitué comme substituants
WO2010024227A1 (fr) 2008-08-25 2010-03-04 参天製薬株式会社 Nouveau dérivé de pyrrole ayant, en tant que substituants, un groupe uréide, un groupe aminocarbonyle et un groupe bicyclique qui peut avoir un substituant
US8088817B2 (en) 2008-08-25 2012-01-03 Santen Pharmaceutical Co., Ltd. Pyrrole derivative having, as substituents, ureido group, aminocarbonly group and bicyclic group which may have substituent
WO2011041461A3 (fr) * 2009-10-01 2011-08-25 Amira Pharmaceuticals, Inc. Composés polycycliques utiles en tant qu'antagonistes du récepteur de l'acide lysophosphatidique
US9624182B2 (en) 2009-10-01 2017-04-18 Amira Pharmaceuticals, Inc. Compounds as lysophosphatidic acid receptor antagonists
JP2013506679A (ja) * 2009-10-01 2013-02-28 アミラ ファーマシューティカルス，インコーポレーテッド リゾホスファチジン酸受容体アンタゴニストとしての多環式化合物
US8217066B2 (en) 2009-10-01 2012-07-10 Amira Pharmaceuticals, Inc. Compounds as lysophosphatidic acid receptor antagonists
US10000456B2 (en) 2009-10-01 2018-06-19 Amira Pharmaceuticals, Inc. Polycyclic compounds as lysophosphatidic acid receptor antagonists
US8664220B2 (en) 2009-10-01 2014-03-04 Amira Pharmaceuticals, Inc. Polycyclic compounds as lysophosphatidic acid receptor antagonists
US8778983B2 (en) 2009-10-01 2014-07-15 Amira Pharmaceuticals, Inc. Polycyclic compounds as lysophosphatidic acid receptor antagonists
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