AU2015289178A1 - Novel compounds - Google Patents
Novel compounds Download PDFInfo
- Publication number
- AU2015289178A1 AU2015289178A1 AU2015289178A AU2015289178A AU2015289178A1 AU 2015289178 A1 AU2015289178 A1 AU 2015289178A1 AU 2015289178 A AU2015289178 A AU 2015289178A AU 2015289178 A AU2015289178 A AU 2015289178A AU 2015289178 A1 AU2015289178 A1 AU 2015289178A1
- Authority
- AU
- Australia
- Prior art keywords
- amino
- carboxyethyl
- mmol
- glutamine
- thio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 373
- 229910052739 hydrogen Inorganic materials 0.000 claims description 145
- 239000001257 hydrogen Substances 0.000 claims description 145
- -1 hydroxy, carboxy, amino Chemical group 0.000 claims description 136
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 93
- 150000003839 salts Chemical class 0.000 claims description 82
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 81
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 75
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 56
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 55
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 37
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 36
- 239000005864 Sulphur Substances 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 35
- 238000011282 treatment Methods 0.000 claims description 33
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 25
- 125000003277 amino group Chemical group 0.000 claims description 23
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- MSFSPUZXLOGKHJ-PGYHGBPZSA-N 2-amino-3-O-[(R)-1-carboxyethyl]-2-deoxy-D-glucopyranose Chemical class OC(=O)[C@@H](C)O[C@@H]1[C@@H](N)C(O)O[C@H](CO)[C@H]1O MSFSPUZXLOGKHJ-PGYHGBPZSA-N 0.000 claims description 17
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 17
- 125000000988 D-alanyl group Chemical group N[C@@H](C(=O)*)C 0.000 claims description 17
- 101001125026 Homo sapiens Nucleotide-binding oligomerization domain-containing protein 2 Proteins 0.000 claims description 17
- 102100029441 Nucleotide-binding oligomerization domain-containing protein 2 Human genes 0.000 claims description 17
- 125000003282 alkyl amino group Chemical group 0.000 claims description 17
- 150000001721 carbon Chemical group 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 230000002757 inflammatory effect Effects 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 13
- 208000023275 Autoimmune disease Diseases 0.000 claims description 12
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 150000001412 amines Chemical group 0.000 claims description 8
- 208000027866 inflammatory disease Diseases 0.000 claims description 8
- 230000008484 agonism Effects 0.000 claims description 7
- 230000009286 beneficial effect Effects 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 16
- UPSFWNANGCRBKF-QYNIQEEDSA-N (2R)-2-amino-5-[[(1S)-2-[(2R)-2-amino-2-carboxyethoxy]-1-carboxyethyl]amino]-5-oxopentanoic acid Chemical compound N[C@H](COC[C@@H](C(=O)O)NC(CC[C@@H](N)C(=O)O)=O)C(=O)O UPSFWNANGCRBKF-QYNIQEEDSA-N 0.000 claims 1
- JITUFSJXEBPOKO-DSYKOEDSSA-N (2R)-2-amino-5-[[(1S)-2-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-carboxyethyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CSC[C@H](C(=O)O)NC(CC[C@@H](N)C(=O)O)=O)C(=O)O JITUFSJXEBPOKO-DSYKOEDSSA-N 0.000 claims 1
- YUVGXTAWQWRDFJ-GJMOJQLCSA-N (2R)-2-amino-5-[[(2S)-3-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CSC[C@H](C(=O)NCC(=O)O)NC(CC[C@@H](N)C(=O)O)=O)C(=O)O YUVGXTAWQWRDFJ-GJMOJQLCSA-N 0.000 claims 1
- KLUWOCLDBGVVRI-LURQLKTLSA-N (2R)-2-amino-5-[[(2S)-3-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-[[(1R)-1-carboxyethyl]amino]-1-oxopropan-2-yl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CSC[C@H](C(=O)N[C@H](C)C(=O)O)NC(CC[C@@H](N)C(=O)O)=O)C(=O)O KLUWOCLDBGVVRI-LURQLKTLSA-N 0.000 claims 1
- SZSWLGYJMYJGLY-KDXUFGMBSA-N (2R)-5-[[(1S)-2-[(2R)-2-amino-2-carboxyethoxy]-1-carboxyethyl]amino]-2-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](C)C(=O)N[C@H](CCC(N[C@@H](COC[C@H](C(=O)O)N)C(=O)O)=O)C(=O)O SZSWLGYJMYJGLY-KDXUFGMBSA-N 0.000 claims 1
- SOHCGOCERGJUKH-AQNXPRMDSA-N (2R)-5-[[(1S)-2-[(2R)-2-amino-2-carboxyethoxy]-1-carboxyethyl]amino]-5-oxo-2-(tetradecanoylamino)pentanoic acid Chemical compound N[C@H](COC[C@@H](C(=O)O)NC(CC[C@@H](NC(CCCCCCCCCCCCC)=O)C(=O)O)=O)C(=O)O SOHCGOCERGJUKH-AQNXPRMDSA-N 0.000 claims 1
- ALKWWXHXTPNSLM-RCCFBDPRSA-N (2R)-5-[[(1S)-2-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-carboxyethyl]amino]-2-(dodecanoylamino)-5-oxopentanoic acid Chemical compound N[C@@H](CSC[C@H](C(=O)O)NC(CC[C@@H](NC(CCCCCCCCCCC)=O)C(=O)O)=O)C(=O)O ALKWWXHXTPNSLM-RCCFBDPRSA-N 0.000 claims 1
- FVIPELJWAODUOX-YNEHKIRRSA-N (2R)-5-[[(1S)-2-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-carboxyethyl]amino]-2-(heptanoylamino)-5-oxopentanoic acid Chemical compound N[C@@H](CSC[C@H](C(=O)O)NC(CC[C@@H](NC(CCCCCC)=O)C(=O)O)=O)C(=O)O FVIPELJWAODUOX-YNEHKIRRSA-N 0.000 claims 1
- PVJGWUAIJLMRJS-XNDJQWLSSA-N (2R)-5-[[(1S)-2-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-carboxyethyl]amino]-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](C(C)C)C(=O)N[C@H](CCC(N[C@H](CSC[C@@H](C(=O)O)N)C(=O)O)=O)C(=O)O PVJGWUAIJLMRJS-XNDJQWLSSA-N 0.000 claims 1
- UESFPRFLIBLIJU-BYNSBNAKSA-N (2R)-5-[[(1S)-2-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-carboxyethyl]amino]-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CC1=CC=CC=C1)C(=O)N[C@H](CCC(N[C@H](CSC[C@@H](C(=O)O)N)C(=O)O)=O)C(=O)O UESFPRFLIBLIJU-BYNSBNAKSA-N 0.000 claims 1
- JSSQUGUOSYCWFG-NNYUYHANSA-N (2R)-5-[[(1S)-2-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-carboxyethyl]amino]-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](CC(C)C)C(=O)N[C@H](CCC(N[C@H](CSC[C@@H](C(=O)O)N)C(=O)O)=O)C(=O)O JSSQUGUOSYCWFG-NNYUYHANSA-N 0.000 claims 1
- BJOQIHALGUKJQD-RBXMUDONSA-N (2R)-5-[[(1S)-2-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-carboxyethyl]amino]-2-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](C)C(=O)N[C@H](CCC(N[C@H](CSC[C@@H](C(=O)O)N)C(=O)O)=O)C(=O)O BJOQIHALGUKJQD-RBXMUDONSA-N 0.000 claims 1
- UGIQWTHCWVOOCP-XUVXKRRUSA-N (2R)-5-[[(1S)-2-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-carboxyethyl]amino]-5-oxo-2-(tetradecanoylamino)pentanoic acid Chemical compound N[C@@H](CSC[C@H](C(=O)O)NC(CC[C@@H](NC(CCCCCCCCCCCCC)=O)C(=O)O)=O)C(=O)O UGIQWTHCWVOOCP-XUVXKRRUSA-N 0.000 claims 1
- FSGMEDSCJVLKAL-IPMKNSEASA-N (2R)-5-[[(2S)-3-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-2-(dodecanoylamino)-5-oxopentanoic acid Chemical compound N[C@@H](CSC[C@H](C(=O)NCC(=O)O)NC(CC[C@@H](NC(CCCCCCCCCCC)=O)C(=O)O)=O)C(=O)O FSGMEDSCJVLKAL-IPMKNSEASA-N 0.000 claims 1
- AYPGWKJBTDIHRP-BFHYXJOUSA-N (2R)-5-[[(2S)-3-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-2-(heptanoylamino)-5-oxopentanoic acid Chemical compound N[C@@H](CSC[C@H](C(=O)NCC(=O)O)NC(CC[C@@H](NC(CCCCCC)=O)C(=O)O)=O)C(=O)O AYPGWKJBTDIHRP-BFHYXJOUSA-N 0.000 claims 1
- PUMMYHDUFHOIDW-AXTSPUMRSA-N (2R)-5-[[(2S)-3-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-2-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](C)C(=O)N[C@H](CCC(N[C@@H](C(=O)NCC(=O)O)CSC[C@@H](C(=O)O)N)=O)C(=O)O PUMMYHDUFHOIDW-AXTSPUMRSA-N 0.000 claims 1
- URJRJJWXOCWPHM-PWRODBHTSA-N (2R)-5-[[(2S)-3-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-(carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxo-2-(tetradecanoylamino)pentanoic acid Chemical compound N[C@@H](CSC[C@H](C(=O)NCC(=O)O)NC(CC[C@@H](NC(CCCCCCCCCCCCC)=O)C(=O)O)=O)C(=O)O URJRJJWXOCWPHM-PWRODBHTSA-N 0.000 claims 1
- STIQEWNZNQRSLR-IYWMVGAKSA-N (2R)-5-[[(2S)-3-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-[[(1R)-1-carboxyethyl]amino]-1-oxopropan-2-yl]amino]-2-(dodecanoylamino)-5-oxopentanoic acid Chemical compound N[C@@H](CSC[C@H](C(=O)N[C@H](C)C(=O)O)NC(CC[C@@H](NC(CCCCCCCCCCC)=O)C(=O)O)=O)C(=O)O STIQEWNZNQRSLR-IYWMVGAKSA-N 0.000 claims 1
- IBQWNVMQKWCXBN-LXTVHRRPSA-N (2R)-5-[[(2S)-3-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-[[(1R)-1-carboxyethyl]amino]-1-oxopropan-2-yl]amino]-2-(heptanoylamino)-5-oxopentanoic acid Chemical compound N[C@@H](CSC[C@H](C(=O)N[C@H](C)C(=O)O)NC(CC[C@@H](NC(CCCCCC)=O)C(=O)O)=O)C(=O)O IBQWNVMQKWCXBN-LXTVHRRPSA-N 0.000 claims 1
- FVOOJOUHCOIGKP-OGBGREFGSA-N (2R)-5-[[(2S)-3-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-[[(1R)-1-carboxyethyl]amino]-1-oxopropan-2-yl]amino]-2-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoic acid Chemical compound N[C@@H](C)C(=O)N[C@H](CCC(N[C@@H](C(=O)N[C@H](C)C(=O)O)CSC[C@@H](C(=O)O)N)=O)C(=O)O FVOOJOUHCOIGKP-OGBGREFGSA-N 0.000 claims 1
- GYLDHWHGASYGDZ-CIAFKFPVSA-N (2R)-5-[[(2S)-3-[(2R)-2-amino-2-carboxyethyl]sulfanyl-1-[[(1R)-1-carboxyethyl]amino]-1-oxopropan-2-yl]amino]-5-oxo-2-(tetradecanoylamino)pentanoic acid Chemical compound N[C@@H](CSC[C@H](C(=O)N[C@H](C)C(=O)O)NC(CC[C@@H](NC(CCCCCCCCCCCCC)=O)C(=O)O)=O)C(=O)O GYLDHWHGASYGDZ-CIAFKFPVSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 657
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 390
- 239000000543 intermediate Substances 0.000 description 314
- 239000000203 mixture Substances 0.000 description 185
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 169
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 140
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 134
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 132
- 239000000243 solution Substances 0.000 description 128
- 238000005481 NMR spectroscopy Methods 0.000 description 120
- 238000000034 method Methods 0.000 description 99
- 238000003818 flash chromatography Methods 0.000 description 97
- 239000000741 silica gel Substances 0.000 description 96
- 229910002027 silica gel Inorganic materials 0.000 description 96
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 94
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 91
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
- 239000012044 organic layer Substances 0.000 description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 87
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 84
- 238000006243 chemical reaction Methods 0.000 description 83
- 239000012043 crude product Substances 0.000 description 77
- 239000002904 solvent Substances 0.000 description 71
- 235000019439 ethyl acetate Nutrition 0.000 description 68
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 64
- 239000012267 brine Substances 0.000 description 57
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 57
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 55
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 54
- 239000011541 reaction mixture Substances 0.000 description 52
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 44
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 42
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- 239000000706 filtrate Substances 0.000 description 24
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- 230000000694 effects Effects 0.000 description 12
- UNSAJINGUOTTRA-UHFFFAOYSA-N 3-(3-bromophenyl)prop-2-yn-1-ol Chemical compound OCC#CC1=CC=CC(Br)=C1 UNSAJINGUOTTRA-UHFFFAOYSA-N 0.000 description 11
- MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 description 11
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 9
- 230000004224 protection Effects 0.000 description 9
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 8
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Classifications
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
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- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
- C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06043—Leu-amino acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06052—Val-amino acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP14177268.1A EP2975046A1 (en) | 2014-07-16 | 2014-07-16 | Novel compounds |
EP14177268.1 | 2014-07-16 | ||
PCT/EP2015/066203 WO2016008946A1 (en) | 2014-07-16 | 2015-07-15 | Novel compounds |
Publications (1)
Publication Number | Publication Date |
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AU2015289178A1 true AU2015289178A1 (en) | 2017-02-16 |
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Family Applications (1)
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AU2015289178A Abandoned AU2015289178A1 (en) | 2014-07-16 | 2015-07-15 | Novel compounds |
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Country | Link |
---|---|
US (1) | US20170210778A1 (und) |
EP (2) | EP2975046A1 (und) |
JP (1) | JP2017528514A (und) |
AU (1) | AU2015289178A1 (und) |
CA (1) | CA2989065A1 (und) |
WO (1) | WO2016008946A1 (und) |
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CA3026074A1 (en) | 2016-06-01 | 2017-12-07 | M3 Biotechnology, Inc. | N-hexanoic-l-tyrosine-l-isoleucine-(6)-aminohexanoic amide compounds and their use to treat neurodegenerative diseases |
US10575469B2 (en) * | 2016-07-14 | 2020-03-03 | Cnh Industrial America Llc | Net wrapping system |
US20230174577A1 (en) * | 2020-03-26 | 2023-06-08 | Nutrivert Llc | Lipophilic enantiomers of desacetylglucosamine muramyl dipeptide with anti-inflammatory and growth promoting activity |
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FR2496654A1 (fr) | 1980-12-19 | 1982-06-25 | Rhone Poulenc Sante | Nouveaux tri-, tetra- et pentapeptides, leur preparation et les medicaments qui les contiennent |
US7078165B2 (en) | 2003-03-27 | 2006-07-18 | Institut Pasteur | Method for modulating Nod1 activity, use of a MTP related molecule for modulating Nod1 activity, and therapeutic applications thereof |
WO2005017177A2 (en) | 2003-05-14 | 2005-02-24 | The Regents Of The University Of The Michigan | Modulators of nod1 signaling |
US20060194740A1 (en) | 2005-02-25 | 2006-08-31 | Ulevitch Richard J | NOD1 as an anti-tumor agent |
GB0520842D0 (en) * | 2005-10-14 | 2005-11-23 | Hofmann Thomas F | Kokumi flavour compounds and use |
JP2012513448A (ja) | 2008-12-22 | 2012-06-14 | ザ・プロウボウスト・フェロウズ・アンド・スカラーズ・オブ・ザ・ホリー・アンド・アンデバイデッド・トリニティ・オブ・クイーン・エリザベス・ニア・ダブリン | 自己免疫疾患および炎症性疾患の処置ための化合物および方法 |
US20130209366A1 (en) * | 2010-08-24 | 2013-08-15 | Oklahoma Medical Research Foundation | Glutathione-Lanthionine Compounds and Methods Related Thereto |
-
2014
- 2014-07-16 EP EP14177268.1A patent/EP2975046A1/en not_active Withdrawn
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2015
- 2015-07-15 EP EP15736524.8A patent/EP3169698B1/en not_active Not-in-force
- 2015-07-15 US US15/326,534 patent/US20170210778A1/en not_active Abandoned
- 2015-07-15 WO PCT/EP2015/066203 patent/WO2016008946A1/en active Application Filing
- 2015-07-15 AU AU2015289178A patent/AU2015289178A1/en not_active Abandoned
- 2015-07-15 JP JP2017522733A patent/JP2017528514A/ja active Pending
- 2015-07-15 CA CA2989065A patent/CA2989065A1/en not_active Abandoned
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EP2975046A1 (en) | 2016-01-20 |
JP2017528514A (ja) | 2017-09-28 |
EP3169698B1 (en) | 2018-12-05 |
CA2989065A1 (en) | 2016-01-21 |
US20170210778A1 (en) | 2017-07-27 |
WO2016008946A1 (en) | 2016-01-21 |
EP3169698A1 (en) | 2017-05-24 |
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