PL219569B1 - Cykliczne tetrapeptydy i ich zastosowanie - Google Patents
Cykliczne tetrapeptydy i ich zastosowanieInfo
- Publication number
- PL219569B1 PL219569B1 PL390493A PL39049310A PL219569B1 PL 219569 B1 PL219569 B1 PL 219569B1 PL 390493 A PL390493 A PL 390493A PL 39049310 A PL39049310 A PL 39049310A PL 219569 B1 PL219569 B1 PL 219569B1
- Authority
- PL
- Poland
- Prior art keywords
- tetrapeptide
- mice
- compound
- cells
- cyclic
- Prior art date
Links
- 125000004122 cyclic group Chemical group 0.000 title abstract description 16
- 230000001506 immunosuppresive effect Effects 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 239000002674 ointment Substances 0.000 claims description 9
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 4
- 125000000539 amino acid group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 abstract description 5
- 229940124589 immunosuppressive drug Drugs 0.000 abstract description 4
- 241000699670 Mus sp. Species 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KASDHRXLYQOAKZ-XDSKOBMDSA-N pimecrolimus Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@H](Cl)[C@H](OC)C1 KASDHRXLYQOAKZ-XDSKOBMDSA-N 0.000 description 12
- 108090000765 processed proteins & peptides Proteins 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 229940020485 elidel Drugs 0.000 description 9
- 210000001165 lymph node Anatomy 0.000 description 9
- 229940112971 protopic Drugs 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 210000004698 lymphocyte Anatomy 0.000 description 6
- 239000002953 phosphate buffered saline Substances 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000010933 acylation Effects 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 5
- 230000001028 anti-proliverative effect Effects 0.000 description 5
- 239000000427 antigen Substances 0.000 description 5
- 102000036639 antigens Human genes 0.000 description 5
- 108091007433 antigens Proteins 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 4
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 208000026935 allergic disease Diseases 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 208000010247 contact dermatitis Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 4
- 230000009610 hypersensitivity Effects 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010014025 Ear swelling Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000012531 culture fluid Substances 0.000 description 3
- 210000005069 ears Anatomy 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229960005330 pimecrolimus Drugs 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 229960001967 tacrolimus Drugs 0.000 description 3
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- ZPGDWQNBZYOZTI-SFHVURJKSA-N (2s)-1-(9h-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 ZPGDWQNBZYOZTI-SFHVURJKSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- JFLSOKIMYBSASW-UHFFFAOYSA-N 1-chloro-2-[chloro(diphenyl)methyl]benzene Chemical compound ClC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 JFLSOKIMYBSASW-UHFFFAOYSA-N 0.000 description 2
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 2
- 108010036949 Cyclosporine Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- WZUVPPKBWHMQCE-UHFFFAOYSA-N Haematoxylin Chemical compound C12=CC(O)=C(O)C=C2CC2(O)C1C1=CC=C(O)C(O)=C1OC2 WZUVPPKBWHMQCE-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 206010040914 Skin reaction Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 230000030833 cell death Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 229960001265 ciclosporin Drugs 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 229960000890 hydrocortisone Drugs 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 210000000440 neutrophil Anatomy 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 229960002429 proline Drugs 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 208000017520 skin disease Diseases 0.000 description 2
- 231100000430 skin reaction Toxicity 0.000 description 2
- 230000035483 skin reaction Effects 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- MJYQFWSXKFLTAY-OVEQLNGDSA-N (2r,3r)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2r,3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O.C1=C(O)C(OC)=CC(C[C@@H](CO)[C@H](CO)CC=2C=C(OC)C(O)=CC=2)=C1 MJYQFWSXKFLTAY-OVEQLNGDSA-N 0.000 description 1
- SJVFAHZPLIXNDH-QFIPXVFZSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 SJVFAHZPLIXNDH-QFIPXVFZSA-N 0.000 description 1
- DQNUGHJJKNFCND-SFHVURJKSA-N (3s)-3-(9h-fluoren-9-ylmethoxycarbonylamino)-4-phenylbutanoic acid Chemical compound C([C@@H](CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 DQNUGHJJKNFCND-SFHVURJKSA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- 102000001493 Cyclophilins Human genes 0.000 description 1
- 108010068682 Cyclophilins Proteins 0.000 description 1
- 229930105110 Cyclosporin A Natural products 0.000 description 1
- 241001124144 Dermaptera Species 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000004889 Interleukin-6 Human genes 0.000 description 1
- 108090001005 Interleukin-6 Proteins 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 229930182821 L-proline Natural products 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- RWCOTTLHDJWHRS-YUMQZZPRSA-N Pro-Pro Chemical compound OC(=O)[C@@H]1CCCN1C(=O)[C@H]1NCCC1 RWCOTTLHDJWHRS-YUMQZZPRSA-N 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000024932 T cell mediated immunity Effects 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 239000012317 TBTU Substances 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
- 238000010162 Tukey test Methods 0.000 description 1
- 239000003875 Wang resin Substances 0.000 description 1
- NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 description 1
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 229930189172 cyclolinopeptide Natural products 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- -1 cyclosporine (CsA) Chemical class 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 210000001339 epidermal cell Anatomy 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000028996 humoral immune response Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 229940100601 interleukin-6 Drugs 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229920006008 lipopolysaccharide Polymers 0.000 description 1
- 230000007108 local immune response Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000001926 lymphatic effect Effects 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 239000003226 mitogen Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 210000005087 mononuclear cell Anatomy 0.000 description 1
- 238000007491 morphometric analysis Methods 0.000 description 1
- 230000021616 negative regulation of cell division Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229940092253 ovalbumin Drugs 0.000 description 1
- 239000004466 pelleted feed Substances 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 108010077112 prolyl-proline Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 231100000444 skin lesion Toxicity 0.000 description 1
- 206010040882 skin lesion Diseases 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- YEENEYXBHNNNGV-XEHWZWQGSA-M sodium;3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoate;(2r,3r,4s,5s,6r)-2-[(2r,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound [Na+].CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C([O-])=O)=C1I.O[C@H]1[C@H](O)[C@@H](CO)O[C@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 YEENEYXBHNNNGV-XEHWZWQGSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000004988 splenocyte Anatomy 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000006433 tumor necrosis factor production Effects 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- 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
- C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
- C07K5/126—Tetrapeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- 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
-
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
-
- 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
- C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/64—Cyclic peptides containing only normal peptide links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL390493A PL219569B1 (pl) | 2010-02-19 | 2010-02-19 | Cykliczne tetrapeptydy i ich zastosowanie |
| RU2012139668/04A RU2568436C2 (ru) | 2010-02-19 | 2011-02-19 | Циклические тетрапептиды и их терапевтическое применение |
| US13/579,933 US20130224232A1 (en) | 2010-02-19 | 2011-02-19 | Cyclic tetrapeptides and therapeutic applications thereof |
| EP11745399.3A EP2536732B1 (en) | 2010-02-19 | 2011-02-19 | Cyclic tetrapeptides and therapeutic applications thereof |
| JP2012554079A JP5901543B2 (ja) | 2010-02-19 | 2011-02-19 | 環式テトラペプチド及びその治療応用 |
| PCT/US2011/025571 WO2011103524A2 (en) | 2010-02-19 | 2011-02-19 | Cyclic tetrapeptides and therapeutic applications thereof |
| KR1020127024471A KR101704665B1 (ko) | 2010-02-19 | 2011-02-19 | 환형 테트라펩티드류 및 이들의 치료적 적용 |
| BR112012020833A BR112012020833A2 (pt) | 2010-02-19 | 2011-02-19 | tetrapeptídeos cíclicos e aplicações terapêuticas destes |
| ES11745399.3T ES2611663T3 (es) | 2010-02-19 | 2011-02-19 | Tetrapéptidos cíclicos y aplicaciones terapéuticas de los mismos |
| CN201180019907.7A CN102858779B (zh) | 2010-02-19 | 2011-02-19 | 环状四肽及其治疗性应用 |
| CA2827694A CA2827694C (en) | 2010-02-19 | 2011-02-19 | Cyclic tetrapeptides and therapeutic applications thereof |
| AU2011217882A AU2011217882B2 (en) | 2010-02-19 | 2011-02-19 | Cyclic tetrapeptides and therapeutic applications thereof |
| IL221535A IL221535A (en) | 2010-02-19 | 2012-08-19 | Cyclic tetrapeptides and their therapeutic applications |
| US13/593,716 US9382292B2 (en) | 2010-02-19 | 2012-08-24 | Cyclic tetrapeptides and therapeutic applications thereof |
| IL224410A IL224410A (en) | 2010-02-19 | 2013-01-27 | Cyclic tetrapeptides and pharmaceuticals containing them |
| US15/201,565 US10238713B2 (en) | 2010-02-19 | 2016-07-04 | Cyclic tetrapeptides and therapeutic applications thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL390493A PL219569B1 (pl) | 2010-02-19 | 2010-02-19 | Cykliczne tetrapeptydy i ich zastosowanie |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL390493A1 PL390493A1 (pl) | 2011-08-29 |
| PL219569B1 true PL219569B1 (pl) | 2015-05-29 |
Family
ID=44483608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL390493A PL219569B1 (pl) | 2010-02-19 | 2010-02-19 | Cykliczne tetrapeptydy i ich zastosowanie |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US20130224232A1 (enExample) |
| EP (1) | EP2536732B1 (enExample) |
| JP (1) | JP5901543B2 (enExample) |
| KR (1) | KR101704665B1 (enExample) |
| CN (1) | CN102858779B (enExample) |
| AU (1) | AU2011217882B2 (enExample) |
| BR (1) | BR112012020833A2 (enExample) |
| CA (1) | CA2827694C (enExample) |
| ES (1) | ES2611663T3 (enExample) |
| IL (2) | IL221535A (enExample) |
| PL (1) | PL219569B1 (enExample) |
| RU (1) | RU2568436C2 (enExample) |
| WO (1) | WO2011103524A2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL219569B1 (pl) | 2010-02-19 | 2015-05-29 | Peptaderm Spółka Z Ograniczoną Odpowiedzialnością | Cykliczne tetrapeptydy i ich zastosowanie |
| WO2016179398A1 (en) | 2015-05-05 | 2016-11-10 | Washington University | Isoform-selective lysine deacetylase inhibitors |
| US10154997B2 (en) | 2015-08-04 | 2018-12-18 | Washington University | Treatment of parasitic diseases using KDAC inhibitor compounds |
| WO2018232285A1 (en) * | 2017-06-16 | 2018-12-20 | University Of Florida Research Foundation, Incorporated | Macrocyclic peptides and derivatives thereof with opioid activity |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862925A (en) | 1973-07-05 | 1975-01-28 | American Home Prod | Preparation of somatotropin release inhibiting factor and intermediates therefor |
| US3842067A (en) | 1973-07-27 | 1974-10-15 | American Home Prod | Synthesis of(des-asn5)-srif and intermediates |
| JPS5726506B2 (enExample) * | 1974-03-08 | 1982-06-04 | ||
| IT1077010B (it) * | 1976-09-01 | 1985-04-27 | Snam Progetti | Processo per la preparazione di copolimeri dell isobutilene contenenti insaturazioni ed atomi di alogeno reattivi |
| US4105603A (en) | 1977-03-28 | 1978-08-08 | The Salk Institute For Biological Studies | Peptides which effect release of hormones |
| JPH0334991A (ja) * | 1989-06-30 | 1991-02-14 | Shionogi & Co Ltd | 環状テトラペプチドおよびその製造法 |
| US5216124A (en) * | 1989-12-15 | 1993-06-01 | G. D. Searle & Co. | Substituted cyclic tetrapeptides |
| US5541287A (en) | 1992-06-09 | 1996-07-30 | Neorx Corporation | Pretargeting methods and compounds |
| US6777217B1 (en) * | 1996-03-26 | 2004-08-17 | President And Fellows Of Harvard College | Histone deacetylases, and uses related thereto |
| US6013763A (en) | 1996-06-04 | 2000-01-11 | Genentech, Inc. | Peptide variants of protein A |
| DE69926061T2 (de) * | 1998-03-23 | 2006-06-01 | Trimeris Inc. | Verfahren und zusammensetzungen zur peptidsynthese (t-20) |
| US6281331B1 (en) | 1998-03-23 | 2001-08-28 | Trimeris, Inc. | Methods and compositions for peptide synthesis |
| DE19816922A1 (de) | 1998-04-16 | 1999-10-21 | Wolfgang Beck | Einfache Synthese von cyclischen Tetrapeptiden aus nichtaktivierten Peptidestern an Metallzentren |
| AUPP505798A0 (en) * | 1998-08-04 | 1998-08-27 | Fujisawa Pharmaceutical Co., Ltd. | Novel compound fr225497 substance |
| KR20010080142A (ko) | 1998-10-13 | 2001-08-22 | 후지야마 아키라 | 사이클릭 테트라펩티드 화합물 및 이의 용도 |
| GB9903087D0 (en) * | 1999-02-12 | 1999-03-31 | Glaxo Group Ltd | Process |
| EP1701969B1 (en) | 2003-12-31 | 2007-10-24 | F.Hoffmann-La Roche Ag | Process for peptide synthesis using a reduced amount of deprotection agent |
| WO2006049597A1 (en) | 2004-10-27 | 2006-05-11 | Avanir Pharmaceuticals | Amino acid-derived compounds as modulators of the reverse cholesterol transport |
| US20080219962A1 (en) * | 2004-12-14 | 2008-09-11 | Biorunx Co., Ltd. | Method to Enhance the Bone Formation Activity of Bmp by Runx2 Acetylation |
| JP2010502574A (ja) | 2006-08-23 | 2010-01-28 | イエダ リサーチ アンド デベロップメント カンパニー リミテッド | Rgdペプチドとポルフィリン又は(バクテリオ)クロロフィル光合成剤とのコンジュゲート及びその使用 |
| KR101595138B1 (ko) | 2008-02-27 | 2016-02-18 | 예다 리서치 앤드 디벨럽먼트 캄파니 리미티드 | 괴사종양의 광역학요법 및 영상용 알지디(박테리오)클로로필 컨쥬게이트 |
| WO2010006267A2 (en) * | 2008-07-11 | 2010-01-14 | University Of Kansas | Cyclic tetrapeptides |
| GB0918579D0 (en) | 2009-10-22 | 2009-12-09 | Imp Innovations Ltd | Gadd45beta targeting agents |
| PL219569B1 (pl) | 2010-02-19 | 2015-05-29 | Peptaderm Spółka Z Ograniczoną Odpowiedzialnością | Cykliczne tetrapeptydy i ich zastosowanie |
-
2010
- 2010-02-19 PL PL390493A patent/PL219569B1/pl unknown
-
2011
- 2011-02-19 WO PCT/US2011/025571 patent/WO2011103524A2/en not_active Ceased
- 2011-02-19 EP EP11745399.3A patent/EP2536732B1/en not_active Not-in-force
- 2011-02-19 CA CA2827694A patent/CA2827694C/en not_active Expired - Fee Related
- 2011-02-19 KR KR1020127024471A patent/KR101704665B1/ko not_active Expired - Fee Related
- 2011-02-19 CN CN201180019907.7A patent/CN102858779B/zh not_active Expired - Fee Related
- 2011-02-19 RU RU2012139668/04A patent/RU2568436C2/ru not_active IP Right Cessation
- 2011-02-19 US US13/579,933 patent/US20130224232A1/en not_active Abandoned
- 2011-02-19 ES ES11745399.3T patent/ES2611663T3/es active Active
- 2011-02-19 JP JP2012554079A patent/JP5901543B2/ja not_active Expired - Fee Related
- 2011-02-19 BR BR112012020833A patent/BR112012020833A2/pt not_active Application Discontinuation
- 2011-02-19 AU AU2011217882A patent/AU2011217882B2/en not_active Ceased
-
2012
- 2012-08-19 IL IL221535A patent/IL221535A/en not_active IP Right Cessation
- 2012-08-24 US US13/593,716 patent/US9382292B2/en not_active Expired - Fee Related
-
2013
- 2013-01-27 IL IL224410A patent/IL224410A/en not_active IP Right Cessation
-
2016
- 2016-07-04 US US15/201,565 patent/US10238713B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US10238713B2 (en) | 2019-03-26 |
| CN102858779A (zh) | 2013-01-02 |
| JP5901543B2 (ja) | 2016-04-13 |
| RU2568436C2 (ru) | 2015-11-20 |
| EP2536732B1 (en) | 2016-10-19 |
| AU2011217882A1 (en) | 2012-10-11 |
| AU2011217882B2 (en) | 2015-02-05 |
| WO2011103524A8 (en) | 2012-09-13 |
| WO2011103524A3 (en) | 2011-12-29 |
| CA2827694C (en) | 2018-09-18 |
| PL390493A1 (pl) | 2011-08-29 |
| CA2827694A1 (en) | 2011-08-25 |
| US20130108655A1 (en) | 2013-05-02 |
| KR101704665B1 (ko) | 2017-02-08 |
| CN102858779B (zh) | 2016-08-03 |
| KR20130088004A (ko) | 2013-08-07 |
| US20130224232A1 (en) | 2013-08-29 |
| US20170157204A1 (en) | 2017-06-08 |
| RU2012139668A (ru) | 2014-03-27 |
| WO2011103524A2 (en) | 2011-08-25 |
| JP2013520440A (ja) | 2013-06-06 |
| ES2611663T3 (es) | 2017-05-09 |
| IL221535A (en) | 2016-08-31 |
| EP2536732A4 (en) | 2014-04-30 |
| BR112012020833A2 (pt) | 2017-12-19 |
| EP2536732A2 (en) | 2012-12-26 |
| IL224410A (en) | 2017-07-31 |
| US9382292B2 (en) | 2016-07-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101479148B1 (ko) | 주형 고정된 펩타이드 모방체 | |
| AU754876B2 (en) | Gamma-glutamyl and beta-aspartyl containing immunomodulator compounds and methods therewith | |
| EP2409988B1 (en) | Peptide fragments for inducing synthesis of extracellular matrix proteins | |
| US8765683B2 (en) | T-140 peptide analogs having CXCR4 super-agonist activity for cancer therapy | |
| ES2532392T3 (es) | Péptidos antimicrobianos | |
| US8933194B2 (en) | Melanocortin-1 receptor-specific linear peptides | |
| KR20120123654A (ko) | 멜라노코르틴-1 수용체 특이적 고리형 펩티드 | |
| WO1986004334A1 (en) | Immunoregulatory peptides | |
| PL219569B1 (pl) | Cykliczne tetrapeptydy i ich zastosowanie | |
| RU2362579C1 (ru) | Фармацевтическая композиция на основе пептида, обладающего противоопухолевым действием | |
| JPH04500666A (ja) | ペプチド化合物 | |
| WO2017152756A1 (zh) | cRGD-厄洛替尼缀合物及其制备方法 | |
| Ali et al. | Cyclization enhances function of linear anti-arthritic peptides | |
| CN1781933B (zh) | 胸腺素α1活性片段环肽类似物及其聚乙二醇化衍生物 | |
| EP2358740A1 (en) | Cyclic peptides and uses thereof | |
| HRP20000265A2 (en) | Methods and compositions for treating rheumatoid arthritis | |
| KR20210003759A (ko) | 멜라노코르틴 수용체-특이적 펩티드 제형 및 위장관-특이적 전달을 위한 방법 | |
| CA2601202A1 (en) | New hybrid oligomers, their preparation process and pharmaceutical compositions containing them | |
| CN101395143A (zh) | 用于治疗疟疾或aids的氮杂杂环化合物 | |
| AU2018293467A1 (en) | Pro-drug peptide with improved pharmaceutical properties | |
| JP2009518308A (ja) | アポトーシスを阻害するための化合物及び方法 | |
| WO2022150362A1 (en) | Poly-arginine derivatives for enhancing brain-derived growth factor to mitigate neurological disorders | |
| HK1033575B (en) | Gamma-glutamyl and beta-aspartyl containing immunomodulator compounds and methods therewith | |
| HK1033575A1 (en) | Gamma-glutamyl and beta-aspartyl containing immunomodulator compounds and methods therewith | |
| HK1161599B (en) | Peptide fragments for inducing synthesis of extracellular matrix proteins |