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    • 专利摘要:

    公开号:ES2576959T9
    申请号:ES12768803.4T
    申请日:2012-10-02
    公开日:2017-05-29
    发明作者:Françoise JUNG；Daniel Obrecht；Ralf LÖWE；Johann Zimmermann；Guillaume Lemercier；Eric Chevalier
    申请人:Polyphor AG；
    IPC主号:
    专利说明:

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    The terms "cycloalkyl-aryl", "heterocycloalkyl-aryl", "cycloalkyl-heteroaryl", and "heterocycloalkyl-heteroaryl", as used herein, are defined analogously to the terms "aryl-cycloalkyl", "arylheterocycloalkyl", "heteroaryl-cycloalkyl" and "heteroaryl-heterocycloalkyl", as defined above,
    5 but connected in the opposite direction, for example, instead of 4– (thiazol-2-yl) piperazinyl, the term refers to 2– (piperazin-1-yl) thiazolyl and the like.
    The terms "hydroxy", "alkoxy" and "aryloxy", taken alone or in combinations, refer to the groups of -OH, -O- alkyl and -O-aryl, respectively, in which an alkyl group or a group aryl is as defined above. The term "Cx-y alkoxy" (each x and y being an integer) refers to an -O-alkyl group, as defined above, containing x a and carbon atoms attached to an oxygen atom. Representative examples of alkoxy groups include methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy and the like. Examples of aryloxy include, for example, phenoxy. For the avoidance of doubt, for example, the term "hydroxy-C1-8 alkyl" represents, among others, groups such as, for example, hydroxymethyl, 1–
    Hydroxypropyl, 2-hydroxypropyl or 3-hydroxy-2,3-dimethylbutyl.
    The term "optionally substituted", in general, is intended to indicate that a group, such as, but not limited to, Cx-y alkyl, Cx-y alkenyl, cycloalkyl, aryl, heteroaryl, heterocycloalkyl, Cx-y alkoxy, and aryloxy it may be substituted with one or more substituents independently selected from amino (-NH2), dimethylamino, nitro (-NO2), halogen (F, Cl, Br, I), CF3, cyano (-CN), hydroxy, methoxy, ethoxy, phenyloxy, benzyloxy, acetoxy, oxo (= O), carboxy, carboxamide, methyl, ethyl, phenyl, benzyl, sulphonic acid, sulfate, phosphonic acid, phosphate or phosphonate.
    In the context of the present invention, the expression "α-amino acid of natural or unnatural origin" comprises
    Typically any natural α-amino acid, such as proteogenic amino acids (examples are listed below), their natural or semisynthetic derivatives and also α-amino acids of purely synthetic origin. This expression also includes α-amino acids that are optionally substituted on the α-nitrogen of the amino acid such as, but not limited to, acetylation or alkylation, for example, methylation or benzylation.
    The term "aliphatic α-amino acid" refers to α-amino acids with an aliphatic side chain, such as, but not limited to, alanine, valine, leucine, isoleucine, n-octylglycine etc.
    The term "aromatic α-amino acid" refers to α-amino acids with a side chain comprising an aromatic or heteroaromatic group, such as, but not limited to, phenylalanine, tryptophan, histidine, O-methyl tyrosine, 4
    Trifluoromethyl-phenylalanine, 3,4-dichloro-homophenylalanine etc.
    The term "α-amino acid cross-linking" refers to α-amino acids with a side chain comprising a function capable of cross-linking to a second α-amino acid through a strong interaction, such as a covalent bond or an electrostatic contact, such as, but not limited to, cysteine, homocysteine, etc.
    The term "α-alcoholic amino acid" refers to α-amino acids with a side chain comprising an alcoholic or thioalcoholic group, that is, a hydroxy or sulfhydryl function, such as, but not limited to, serine, threonine, etc.
    For the avoidance of doubt, the expression "simple side chain" in the context of an α-amino acid refers to a
    Structure in which the α-carbon of the amino acid is covalently connected to the groups (in the chain) of the carbonyl (C = O)) and nitrogen (N), as well as to a hydrogen (H) and a variable side chain, for example as defined above. A "single side chain" may also include a heterocyclic structure comprising the α-amino atom, such as, but not limited to, proline, pipecolic acid etc.
    For the avoidance of doubt, the term "heteroatom" refers to any atom that is not carbon or hydrogen.
    Descriptors L and D, respectively, refer to stereochemistry at the α position of an α-amino acid and are used according to the Fischer-Rosanoff convention of the IUPAC.
    The peptidomimetics of the present invention may also be diastereomers (eg, epimers) of the compounds of formula (I) if no specific stereochemistry of the chiral center is determined in the description. These stereoisomers can be prepared by a modification of the process described below in which the appropriate isomers (eg, epimers / enantiomers) of the chiral starting materials are used. In the event that in the above description the stereochemistry is ambiguous, each individual epimer is part of the present invention, as well as a mixture of both.
    A further embodiment of the present invention may also include compounds, which are identical to the compounds of formula (I), except that one or more atoms are substituted by an atom having an atomic mass number or mass number different from the mass number Atomic or mass number normally found in nature, for example, compounds enriched in 2H (D), 3H, 11C, 14C, 127I etc. These isotopic analogs and their salts and pharmaceutical formulations are considered useful agents in therapy and / or diagnosis, for example,
    9


    but without limitations, in which a fine adjustment of the in vivo half-life could lead to an optimized dosing regimen.
    A further particular embodiment of the present invention relates to derivatives of the general formula (I), in which specifically
    T1 is a D α-amino acid residue of one of the formulas AA1D; AA3D; AA4D; AA5D; or AA8D. T2 is an α-amino acid residue of one of the formulas AA1; AA2; AA3; AA4; AA5; AA6; or AA8; and P7 is a D α-amino acid residue of one of the formulas AA1D; AA4D; AA5D; or AA8D;
    A particular alternative embodiment of the present invention relates to derivatives of the general formula (I), in which specifically
    T1 is a D α-amino acid residue of one of the formulas AA4D; AA5D, AA6D; AA7D; AA8D; or AA9D; and T2 is an α-amino acid residue of one of the formulas AA4; AA5; AA6; AA7; AA8; or AA9;
    In another particular embodiment of the present invention, the elements of the general formula (I) are defined as follows P1, P3, P13 and P14 are independently Gly; Gly (tBu); Gly (cHex); Gly (cPr); To; Ala (tBu); Ala (cHex); Ala (cPr); Val; Nva; Leu; Ile; Nle; hLeu; OctG; Met; Wing (Ppz); Dab; Dab (Ac); Dab (cPr); Dab (iPr); Dab (MeSO2); Dap; Dap (Ac);
    25 Dap (cPr); Dap (iPr); Dap (MeSO2); Lys; Lys (Bz); Lys (Me); Lys (Nic); Lys ((5R) OH); Lys (4Oxa); hLys; Orn; Orn (Ac); Orn (cPr); Orn (iPr); Arg; hArg; Asn; Asp; Gln; Glu; Cit; Met (O2); Be; hSer; Be (Bn); Be (Me); Thr; aloThr; Thr (Bn); Thr (Me); Beep; Bbta; 2Pal; 3Pal; 4Pal; h2Pal; h3Pal; h4Pal; Ala (2Furyl); Ala (3Furyl); Ala (1lm); Wing (2lm); hAla (1lm); hAla (2lm); Wing (Pyrazinyl); Ala (1 Pyrazolyl); Ala (3 Pyrazolyl); Ala (2Pirimidine); Ala (4Pirimidine); Ala (5Pirimidine); Wing (2Quin); Ala (3Quin); Ala (4Quin); Phe; Phe (2Cl); Phe (3Cl); Phe (4Cl); Phe (3,4Cl2); Phe (2F); Phe (3F); Phe (4F); Phe (3CN); Phe (4CN); Phe (2CF3); Phe (3CF3); Phe (4CF3); Phe (3.4 (CF3) 2); Phe (4COOMe); hPhe; Phg; 1Nal; 2Nal; Nle (6OBn); Trp; Trp (7Aza); Trp (5Br); Trp (6Br); Trp (6CF3); Trp (5Cl); Trp (6Cl); Trp (5.6Cl); Trp (5OH); hTrp; His; His (Me); His (Bn); hHis; Thi; Thz; Thz (5.5Me2); Tic; Tic (7OH); Tyr; Tyr (Bn); Tyr (Me); Tyr (Ph); Tyr (4OHPh); hTyr; or Tza; P2, P5 and P8 are independently
    35 2Pal; 3Pal; 4Pal; h2Pal; h3Pal; h4Pal; Ala (2Furyl); Ala (3Furyl); Ala (1lm); Wing (2lm); hAla (1lm); hAla (2lm); Wing (Pyrazinyl); Ala (1 Pyrazolyl); Ala (3 Pyrazolyl); Ala (2Pirimidine); Ala (4Pirimidine); Ala (5Pirimidine); Wing (2Quin); Ala (3Quin); Ala (4Quin); Phe; Phe (2Cl); Phe (3CI); Phe (4Cl); Phe (3,4Cl2); Phe (2F); Phe (3F); Phe (4F); Phe (3CN); Phe (4CN); Phe (2CF3); Phe (3CF3); Phe (4CF3); Phe (3.4 (CF3) 2); Phe (4COOMe); hPhe; Phg; 1Nal; 2Nal; Nle (6OBn); Trp; Trp (7Aza); Trp (5Br); Trp (6Br); Trp (6CF3); Trp (5Cl); Trp (6Cl); Trp (5.6CI); Trp (5OH); hTrp; His; His (Me); His (Bn); hHis; Thi; Thz; Thz (5.5Me2); Tic; Tic (7OH); Tyr; Tyr (Bn); Tyr (Me); Tyr (Ph); Tyr (4OHPh); hTyr; or Tza; P4 and P11 are independently Cys; or hCys; P6 is Gly; P7 is DAla; DPro; DPro ((4R) OH); or DTic;
    45 P9 is Ser; hSer; Thr; aloThr; P10 is Gly; Gly (tBu); Gly (cHex); Gly (cPr); To; Ala (tBu); Ala (cHex); Ala (cPr); Val; Nva; Leu; Ile; Nle; hLeu; or OctG; and P12 is Ser; hSer; Thr; aloThr; 2Pal; 3Pal; 4Pal; h2Pal; h3Pal; h4Pal; Ala (2Furyl); Ala (3Furyl); Ala (1lm); Wing (2lm); hAla (1lm); hAla (2lm); Wing (Pyrazinyl); Ala (1 Pyrazolyl); Ala (3 Pyrazolyl); Ala (2Pirimidine); Ala (4Pirimidine); Ala (5 Pyrimidine); Wing (2Quin); Ala (3Quin); Ala (4Quin); Phe; Phe (2Cl); Phe (3CI); Phe (4Cl); Phe (3,4Cl2); Phe (2F); Phe (3F); Phe (4F); Phe (3CN); Phe (4CN); Phe (2CF3); Phe (3CF3); Phe (4CF3); Phe (3.4 (CF3) 2); Phe (4COOMe); hPhe; Phg; 1Nal; 2Nal; Trp; Trp (7Aza); Trp (5Br); Trp (6Br); Trp (6CF3); Trp (5Cl); Trp (6Cl); Trp (5.6Cl); Trp (5OH); hTrp; His; His (Me); His (Bn); hHis; Thi; Thz; Thz (5.5Me2); Tic; Tic (7OH); Tyr; Tyr (Bn); Tyr (Me); Tyr (Ph); Tyr (4OHPh); hTyr; or Tza;
    or pharmaceutically acceptable salts thereof.
    In a further particular embodiment of the present invention, the elements of the general formula (I) are defined as follows T1 is DAla; DLys; DPro; DPro ((4S) NH2); DPro ((4S) OH); DPip; DThr; or DTic; T2 is Ala; Dab; Lys; Glu; Pro; Pro ((4R) NH2); Pro ((4S) NH2); Pro ((4R) OH); Pro ((4S) OH); Pip; Tic; Oic; or Trp; P1, P3, P13 and P14 are independently Gly; Gly (tBu); Gly (cHex); Gly (cPr); To; Ala (tBu); Ala (cHex); Ala (cPr); Val; Nva; Leu; Ile; Nle; hLeu; OctG; Met; Wing (Ppz); Dab; Dab (Ac); Dab (cPr); Dab (iPr); Dab (MeSO2); Dap; Dap (Ac); Dap (cPr); Dap (iPr); Dap (MeSO2); Lys; Lys (Bz); Lys (Me); Lys (Nic); Lys ((5R) OH); Lys (4Oxa); hLys; Orn; Orn (Ac); Orn (cPr); Orn (iPr); Arg; hArg; Asn; Asp; Gln; Glu; Cit; Met (O2); Be; hSer; Be (Bn); Be (Me); Thr; aloThr; Thr (Bn); Thr (Me); Beep; Bbta; 2Pal; 3Pal; 4Pal; h2Pal; h3Pal; h4Pal; Ala (2Furyl); Ala (3Furyl); Ala (1lm); Wing (2lm); hAla (1lm); hAla (2lm); Wing (Pyrazinyl); Ala (1 Pyrazolyl);
    65 Ala (3 Pyrazolyl); Ala (2Pirimidine); Ala (4Pirimidine); Ala (5Pirimidine); Wing (2Quin); Ala (3Quin); Ala (4Quin); Phe; Phe (2Cl); Phe (3Cl); Phe (4Cl); Phe (3,4Cl2); Phe (2F); Phe (3F); Phe (4F); Phe (3CN); Phe (4CN); Phe (2CF3); Phe (3CF3);
    10
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    Lys L-lysine
    Met L-methionine
    Orn L-Ornithine
    Phe L-phenylalanine
    5 ProL-proline
    Be L-serine
    Thr L-threonine
    Trp L-tryptophan
    Tyr L-tyrosine
    Val L-valine
    fifteen Wing (tBu) Wing (cHex) Wing (cPr) Wing (2Furyl) Wing (3Furyl)(S) –2 – amino – 4,4-dimethylpentanoic acid (S) –2 – amino-3-cyclohexylpropanoic acid (S) –2 – amino-3-cyclopropylpropanoic acid (S) –2 – amino-3– ( furan-2-yl) propanoic acid (S) –2 – amino-3– (furan-3-yl) propanoic acid
    Wing (1lm) Wing (2lm) Wing (Ppz) Wing (cPr) (S) –2 – amino-3– (1H – imidazol-1-yl) propanoic acid (S) –2 – amino-3– (1H – imidazol-2-yl) propanoic acid (S) –2 – amino -3– (piperazin-1-yl) propanoic acid (S) –2 – amino-3 – cyclopropylpropanoic acid
    Wing (Pyrazinyl) Wing (1 Pyrazolyl) Wing (3 Pyrazolyl) Wing (2 Pyrimidine) (S) –2 – amino-3– (pyrazin-2-yl) propanoic acid (S) –2 – amino-3– (1H – pyrazol-1-yl) propanoic acid (S) –2 – amino-3 - (1H – pyrazol-3-yl) propanoic acid (S) –2 – amino-3– (pyrimidin-2-yl) propanoic acid
    25 Ala (4Pirimidina) Ala (5Pirimidina) Ala (2Quin) Ala (3Quin)(S) –2 – amino-3– (pyrimidin-4-yl) propanoic acid (S) –2 – amino-3– (pyrimidin-5-yl) propanoic acid (S) –2 – amino-3– ( quinolin-2-yl) propanoic acid (S) –2 – amino-3– (quinolin-3-yl) propanoic acid
    Wing (4Quin) Bbta Bip Dab (S) –2 – amino-3– (quinolin-4-yl) propanoic acid (S) –2 – amino-3– (1-benzothiophene-3-yl) propanoic acid (S) –2 – amino-3 - (4-biphenylyl) propanoic acid (S) -2,4-diaminobutanoic acid
    35 Dab (Ac) Dab (cPr) Dab (iPr) Dab (MeSO2)(S) –4 – acetamido – 2 – aminobutanoic acid (S) –2 – amino-4- (cyclopropylamino) butanoic acid (S) –2 – amino-4- (isopropylamino) butanoic acid (S) –2 – amino -4- (methylsulfonamido) butanoic
    Dap Dap (Ac) Dap (cPr) Dap (iPr) (S) -2,3-diaminopropanoic acid (S) -3-acetamido-2-aminopropanoic acid (S) -2-amino-3- (cyclopropylamino) propanoic acid (S) -2-amino-3- (isopropylamino ) propanoic
    Dap (MeSO2) Gly (tBu) Gly (cHex) Gly (cPr) (S) -2-amino-3- (methylsulfonamido) propanoic acid (S) -2-amino-3,3-dimethylbutanoic acid (S) -2-amino-2-cyclohexylacetic acid (S) -2-amino- 2 – cyclopropylacetic
    Four. Five hAla (1lm) hAla (2lm) hArg hCha hCys(S) –2 – amino-3– (1H – imidazol-1-yl) butanoic acid (S) –2 – amino-3– (1H – imidazol-2-yl) butanoic acid (S) –2 – amino -6 – guanidinohexanoic acid (S) –2 – amino-4 – cyclohexylbutanoic acid (S) –2 – amino-4 – mercaptobutanoic acid
    hHis hLeu hLys h2Pal (S) –2 – amino-4– (1 H –imidazol-5-yl) butanoic acid (S) –2 – amino-5-methylhexanoic acid (S) -2,7 – diaminoheptanoic acid (S) –2– amino-4– (pyridin-2-yl) –butanoic
    55 h3Pal h4Pal hPhe hSer(S) –2 – amino-3– (pyridin-3-yl) –butanoic acid (S) –2 – amino-3– (pyridin-4-yl) –butanoic acid (S) –2 – amino-4 –Phenylbutanoic acid (S) –2 – amino-4 – hydroxybutanoic acid
    hTrp hTyr His (Me) His (Bn) (S) –2 – amino-4– (1H – indole-3-yl) butanoic acid (S) –2 – amino-4- (4-hydroxyphenyl) butanoic acid (S) –2 – amino-3– ( 1-methyl-1H-imidazol-5-yl) propanoic acid (S) –2-amino-3– (1-benzyl-1H-imidazol-5-yl) propanoic acid
    Lys (Bz) Lys (Me) Lys (Nic) Met (O2) (S) –2 – amino-6 – benzamidohexanoic acid (S) –2 – amino-6– (methylamino) hexanoic acid (S) –2 – amino-6– (nicotinamide) hexanoic acid (S) –2 – amino -4- (methylsulfonyl) butanoic acid
    65 1Nal 2Nal(S) –2 – amino-3-naphthalen – 1-ylpropanoic acid (S) –2 – amino-3-naphthalen-2-ylpropanoic acid
    12
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    Boc / t-Bu compatible with this protection scheme. Other linkers that are suitable for the processes of the present invention include the 4– (2,4-dimethoxyphenyl-hydroxymethyl) -phenoxy super labile acid linker (Rink, Rink, H. Tetrahedron Lett. 1987, 28, 3787 linker 3790), in which the removal of the peptide requires 10% acetic acid in DCM or 0.2% trichloroacetic acid in DCM; the acid-derived linker 4– (4–
    5-hydroxymethyl-3-methoxy-phenoxy) butyric (HMPB linker, Flörsheimer & Riniker, Peptides 1991.1990 131) which is also cleaved with 1% TFA / DCM in order to give a peptide fragment containing all the side chain protecting groups labile in acidic media; and, in addition, the 2-chlorotrityl chloride linker (Barlos et al., Tetrahedron Lett. 1989, 30, 3943-3946), which allows peptide release using a mixture of glacial acetic acid / trifluoroethanol / DCM (1: 2: 7) for about 30 minutes.
    Suitable protecting groups for amino acids and, respectively, for their moieties are, for example,
    - for the amino group (as it is present, for example, also in the lysine side chain)
    15 Cbz benzyloxycarbonyl Boc tert-butoxycarbonyl Fmoc 9-fluorenylmethoxycarbonyl Alloc allyloxycarbonyl Teoc trimethylsilylethoxycarbonyl Tcc trichloroethoxycarbonyl Nps o-nitrophenylsulfonyl Trt triphenylmethyl or trityl
    -for the carboxyl group (as it is present, for example, also in the side chain of aspartic and glutamic acid) by conversion into esters with the alcohol components
    tBu tert-butyl Bn benzyl Me methyl Ph phenyl Pac phenylalkyl Tse trimethylsilylethyl Tce trichlorethyl
    35 -for the guanidino group (as it is present, for example, in the arginine side chain)
    Pmc 2,2,5,7,8-pentamethylchroman-6-sulfonyl Ts tosyl (ie, p-toluenesulfonyl) Cbz benzyloxycarbonyl Pbf 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl
    - for the hydroxy group (as it is present, for example, in the threonine and serine side chain)
    tBu tert-butyl 45 Bn benzyl Trt trityl
    - and for the mercapto group (as it is present, for example, in the cysteine side chain)
    Acm acetamidomethyl tBu tert-butyl Bn benzyl Trt trityl Mtr 4-methoxytrityl.
    The amino acid derivatives protected with 9-fluorenylmethoxycarbonyl (Fmoc) are preferably used as building blocks for the construction of the loop fork mimetics β fixed to the template of formula (I). For deprotection, that is, excision of the Fmoc group, 20% piperidine in 2% DMF or 2% DBU / piperidine in DMF can be used.
    The amount of the reactant, ie the amino acid derivative, is generally 1 to 20 equivalents based on the milliequivalents per gram (meq / g) of charge of the functionalized solid support (typically 0.1 to 2.85 meq / g for polystyrene resins) initially weighed in the reaction tube. If necessary, additional equivalents of reactants can be used to direct the reaction to completion in a reasonable time. The reaction tubes 65, in combination with the support block and the manifold, are reinserted into the reservoir block and the apparatus is fixed. Gas flow is initiated through the manifold to provide a controlled environment, for example,
    17
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    权利要求:
    Claims (1)
    [1]
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    引用文献:
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    BRPI0215855B1|2002-08-20|2016-12-13|Polyphor Ltd|matrix-linked cyclic peptides with antimicrobial action|
    AU2003232253A1|2003-05-02|2004-11-23|Polyphor Ag|Template-fixed beta-hairpin peptidomimetics with cxcr4 antagonizing activity|
    WO2005075505A1|2004-02-04|2005-08-18|Postech Foundation|Peptides that antagonize fpr class receptor mediated signaling|
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    PL2132221T3|2007-02-28|2011-04-29|Polyphor Ltd|Template-fixed peptidomimetics|
    WO2010060479A1|2008-11-26|2010-06-03|Polyphor Ag|Template-fixed beta-hairpin peptidomimetics with cxcr4 antagonizing activity|
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    EP3201218B1|2014-09-30|2021-11-03|Polyphor Ag|Beta-hairpin peptidomimetics|
    WO2016150576A1|2015-03-23|2016-09-29|Polyphor Ag|Beta-hairpin peptidomimetics|
    CN111925411A|2017-06-29|2020-11-13|安徽省农业科学院农产品加工研究所|Cys-Ser-containing high-zinc-chelating-activity zinc chelating peptide and application thereof|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    EP11008121|2011-10-07|
    EP11008121|2011-10-07|
    PCT/EP2012/069412|WO2013050346A1|2011-10-07|2012-10-02|Template -fixed peptidomimetics as inhibitors of fpr1|
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