DE60133654T2 - Arzneimittel enthaltend analgetische peptide - Google Patents
Arzneimittel enthaltend analgetische peptide Download PDFInfo
- Publication number
- DE60133654T2 DE60133654T2 DE60133654T DE60133654T DE60133654T2 DE 60133654 T2 DE60133654 T2 DE 60133654T2 DE 60133654 T DE60133654 T DE 60133654T DE 60133654 T DE60133654 T DE 60133654T DE 60133654 T2 DE60133654 T2 DE 60133654T2
- Authority
- DE
- Germany
- Prior art keywords
- peptide
- trp
- amino acid
- asn
- pglu
- 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.)
- Expired - Lifetime
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 63
- 230000000202 analgesic effect Effects 0.000 title claims abstract description 20
- 239000003814 drug Substances 0.000 title claims description 19
- 229940079593 drug Drugs 0.000 title claims description 6
- 102000004196 processed proteins & peptides Human genes 0.000 title description 12
- 150000001413 amino acids Chemical group 0.000 claims abstract description 28
- 150000008575 L-amino acids Chemical class 0.000 claims abstract description 22
- 208000002193 Pain Diseases 0.000 claims abstract description 22
- 230000036407 pain Effects 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 230000000699 topical effect Effects 0.000 claims abstract description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 4
- 230000002265 prevention Effects 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([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 3
- 238000000034 method Methods 0.000 abstract description 11
- 238000002360 preparation method Methods 0.000 abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 238000011200 topical administration Methods 0.000 abstract description 2
- 241000124008 Mammalia Species 0.000 abstract 1
- 235000001014 amino acid Nutrition 0.000 description 20
- 239000000203 mixture Substances 0.000 description 14
- 239000002674 ointment Substances 0.000 description 13
- -1 Leu Chemical compound 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 241000699800 Cricetinae Species 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 7
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Chemical group NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 5
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 230000036592 analgesia Effects 0.000 description 3
- 239000000730 antalgic agent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 210000002569 neuron Anatomy 0.000 description 3
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 239000003998 snake venom Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- WXYGVKADAIJGHB-ZDUSSCGKSA-N (2s)-3-(1h-indol-2-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC=C2NC(C[C@H](NC(=O)OC(C)(C)C)C(O)=O)=CC2=C1 WXYGVKADAIJGHB-ZDUSSCGKSA-N 0.000 description 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 description 2
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 229940039717 lanolin Drugs 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000010647 peptide synthesis reaction Methods 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000012508 resin bead Substances 0.000 description 2
- 230000009155 sensory pathway Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- 239000002435 venom Substances 0.000 description 2
- 231100000611 venom Toxicity 0.000 description 2
- 210000001048 venom Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- DYWUPCCKOVTCFZ-LBPRGKRZSA-N (2s)-2-amino-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]propanoic acid Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C=C(C[C@H](N)C(O)=O)C2=C1 DYWUPCCKOVTCFZ-LBPRGKRZSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 241000271527 Crotalus adamanteus Species 0.000 description 1
- 101500007657 Crotalus durissus terrificus Crotoxin chain gamma Proteins 0.000 description 1
- 241000272060 Elapidae Species 0.000 description 1
- 206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical group C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 241000272139 Naja melanoleuca Species 0.000 description 1
- 102000050267 Neurotensin Human genes 0.000 description 1
- 101800001814 Neurotensin Proteins 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 102000001490 Opioid Peptides Human genes 0.000 description 1
- 108010093625 Opioid Peptides Proteins 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 241000271897 Viperidae Species 0.000 description 1
- 239000003875 Wang resin Substances 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000012466 analgesic assay Methods 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 210000002414 leg Anatomy 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 230000007433 nerve pathway Effects 0.000 description 1
- PCJGZPGTCUMMOT-ISULXFBGSA-N neurotensin Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 PCJGZPGTCUMMOT-ISULXFBGSA-N 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000006461 physiological response Effects 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 108010004034 stable plasma protein solution Proteins 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 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
- 125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 238000005406 washing Methods 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
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
- C07K5/0825—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Glp-amino acid; Derivatives thereof
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- 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
- C07K5/10—Tetrapeptides
- C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL137820A IL137820A (en) | 2000-08-10 | 2000-08-10 | Pharmaceutical composition for topical administration comprising an analgesic peptide |
| IL13782000 | 2000-08-10 | ||
| PCT/IL2001/000724 WO2002012269A2 (en) | 2000-08-10 | 2001-08-06 | Pharmaceutical composition comprising an analgesic peptide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60133654D1 DE60133654D1 (de) | 2008-05-29 |
| DE60133654T2 true DE60133654T2 (de) | 2009-06-04 |
Family
ID=11074512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60133654T Expired - Lifetime DE60133654T2 (de) | 2000-08-10 | 2001-08-06 | Arzneimittel enthaltend analgetische peptide |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7220725B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1309613B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4860096B2 (cg-RX-API-DMAC7.html) |
| CN (2) | CN102160890B (cg-RX-API-DMAC7.html) |
| AT (1) | ATE392428T1 (cg-RX-API-DMAC7.html) |
| AU (2) | AU8005201A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2418793C (cg-RX-API-DMAC7.html) |
| DE (1) | DE60133654T2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK1309613T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2305096T3 (cg-RX-API-DMAC7.html) |
| IL (1) | IL137820A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2002012269A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL137820A (en) * | 2000-08-10 | 2009-06-15 | S I S Shulov Inst For Science | Pharmaceutical composition for topical administration comprising an analgesic peptide |
| US8252754B2 (en) * | 2005-03-21 | 2012-08-28 | The Trustees Of Columbia University In The City Of New York | Neuronal pain pathway |
| US20100190723A1 (en) * | 2007-03-23 | 2010-07-29 | Hiroo Sanada | Preventive or therapeutic composition for liver disease |
| US20110183925A1 (en) * | 2008-09-22 | 2011-07-28 | Nisshin Pharma Inc. | Anti-inflammatory peptide |
| CN102686221B (zh) | 2009-07-27 | 2018-04-17 | 诺西赛普塔有限责任公司 | 治疗疼痛的方法 |
| FR2948809B1 (fr) * | 2009-07-31 | 2012-08-17 | St Microelectronics Rousset | Amplificateur de lecture faible puissance auto-minute |
| ES2598829T3 (es) * | 2011-03-28 | 2017-01-30 | S.I.S. Shulov Innovative Science Ltd. | Procedimiento de tratamiento de trastornos cutáneos |
| CN107847552B (zh) | 2015-01-07 | 2022-07-01 | 三叉神经股份公司 | 含镁的催产素制剂和使用方法 |
| EP4541348A3 (en) | 2016-04-12 | 2025-06-04 | Tonix Pharma Limited | Magnesium-containing oxytocin formulations and methods of use |
| RU2669386C1 (ru) * | 2017-08-11 | 2018-10-11 | Закрытое акционерное общество "Институт экспериментальной фармакологии" | Состав и способ получения анальгетического средства пептидной структуры |
| KR20200138326A (ko) | 2018-03-29 | 2020-12-09 | 에스.아이.에스. 슐로브 이노베이티브 사이언스 리미티드 | 염증성 시토카인을 억제하기 위한 약제학적 조성물 |
| US11644463B2 (en) | 2019-08-30 | 2023-05-09 | Euroimmun Medizinische Labordiagnostika Ag | Detection of an autoantibody |
| AU2020356605A1 (en) * | 2019-09-26 | 2022-04-14 | S.I.S. Shulov Innovative Science Ltd. | Anti-aging compositions and methods of use thereof |
| WO2021059267A1 (en) * | 2019-09-26 | 2021-04-01 | S.I.S. Shulov Innovative Science Ltd. | Compositions and methods for treating degenerative, age-related and trauma-induced disorders |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4491541A (en) * | 1982-11-10 | 1985-01-01 | Farmitalia Carlo Erba | Peptides |
| IT1172391B (it) * | 1983-12-23 | 1987-06-18 | Polifarma Spa | Composti tirpeptidici contenenti acido piroglutaminico e triptofano,procedimentio di produzione ed applicazioni terapeutiche |
| JPH0680079B2 (ja) * | 1984-11-09 | 1994-10-12 | エーザイ株式会社 | ポリペプチド |
| IT1242002B (it) * | 1990-10-03 | 1994-02-02 | Polifarma Spa | Composti con attivita' farmacologica antiipertensiva, analgesica, immunomodulante e antiinfiammatoria, che presentano nella molecola una sequenza di tre radicali, essendo alfa-amminoacido quello centrale |
| EP0668770A1 (en) | 1991-04-24 | 1995-08-30 | Warner-Lambert Company | $g(a)-SUBSTITUTED POLYPEPTIDES HAVING THERAPEUTIC ACTIVITY |
| AUPM489194A0 (en) * | 1994-04-07 | 1994-04-28 | Luminis Pty Limited | Peptides |
| RU2107691C1 (ru) * | 1995-03-02 | 1998-03-27 | Дейгин Владислав Исакович | Пептид и способ его получения |
| US5776896A (en) * | 1996-01-03 | 1998-07-07 | Zeneca Limited | Analgesic peptides from venom of grammostola spatulata and use thereof |
| AU3136897A (en) * | 1996-05-22 | 1997-12-09 | Diversified Pharmaceuticals, Inc. | Compositions, methods and devices for the transdermal delivery of drugs |
| US6126939A (en) * | 1996-09-03 | 2000-10-03 | Yeda Research And Development Co. Ltd. | Anti-inflammatory dipeptide and pharmaceutical composition thereof |
| IL123001A (en) * | 1998-01-20 | 1998-12-06 | Shulov Inst For Venom Research | Analgesic fraction from snake March and pharmacy preparations containing it |
| CA2341810A1 (en) * | 1998-08-28 | 2000-03-09 | Myelos Corporation | Cyclic prosaposin-derived peptides and uses thereof |
| IL137820A (en) * | 2000-08-10 | 2009-06-15 | S I S Shulov Inst For Science | Pharmaceutical composition for topical administration comprising an analgesic peptide |
-
2000
- 2000-08-10 IL IL137820A patent/IL137820A/en active IP Right Grant
-
2001
- 2001-08-06 JP JP2002518242A patent/JP4860096B2/ja not_active Expired - Lifetime
- 2001-08-06 CN CN2011100520229A patent/CN102160890B/zh not_active Expired - Lifetime
- 2001-08-06 AU AU8005201A patent/AU8005201A/xx active Pending
- 2001-08-06 ES ES01958334T patent/ES2305096T3/es not_active Expired - Lifetime
- 2001-08-06 US US10/344,129 patent/US7220725B2/en not_active Expired - Lifetime
- 2001-08-06 CN CN01816060A patent/CN1462277A/zh active Pending
- 2001-08-06 WO PCT/IL2001/000724 patent/WO2002012269A2/en not_active Ceased
- 2001-08-06 AT AT01958334T patent/ATE392428T1/de not_active IP Right Cessation
- 2001-08-06 CA CA2418793A patent/CA2418793C/en not_active Expired - Lifetime
- 2001-08-06 EP EP01958334A patent/EP1309613B1/en not_active Expired - Lifetime
- 2001-08-06 DK DK01958334T patent/DK1309613T3/da active
- 2001-08-06 AU AU2001280052A patent/AU2001280052B2/en not_active Expired
- 2001-08-06 DE DE60133654T patent/DE60133654T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2418793A1 (en) | 2002-02-14 |
| EP1309613A2 (en) | 2003-05-14 |
| CA2418793C (en) | 2011-11-15 |
| CN1462277A (zh) | 2003-12-17 |
| JP2004513079A (ja) | 2004-04-30 |
| CN102160890B (zh) | 2013-02-06 |
| US7220725B2 (en) | 2007-05-22 |
| AU2001280052B2 (en) | 2007-11-29 |
| IL137820A0 (en) | 2001-10-31 |
| JP4860096B2 (ja) | 2012-01-25 |
| DE60133654D1 (de) | 2008-05-29 |
| ATE392428T1 (de) | 2008-05-15 |
| IL137820A (en) | 2009-06-15 |
| AU8005201A (en) | 2002-02-18 |
| EP1309613B1 (en) | 2008-04-16 |
| CN102160890A (zh) | 2011-08-24 |
| US20040014673A1 (en) | 2004-01-22 |
| WO2002012269A3 (en) | 2002-12-19 |
| HK1160778A1 (en) | 2012-08-17 |
| WO2002012269A2 (en) | 2002-02-14 |
| DK1309613T3 (da) | 2008-08-11 |
| ES2305096T3 (es) | 2008-11-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0067425B1 (de) | Gegebenenfalls geschützte Peptide, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE3100974C2 (cg-RX-API-DMAC7.html) | ||
| DE68923401T2 (de) | Peptide mit T-Zellen-Helfer-Wirksamkeit. | |
| DD156968A5 (de) | Verfahren zur herstellung von neuen angiotensin-ii antagonisierenden oktapeptidestern | |
| DE60133654T2 (de) | Arzneimittel enthaltend analgetische peptide | |
| AU2001280052A1 (en) | Pharmaceutical composition comprising an analgesic peptide | |
| DE2822951A1 (de) | Neue polypeptide mit thymusaktivitaet oder antagonistischer aktivitaet und verfahren zu ihrer herstellung | |
| CH676425A5 (cg-RX-API-DMAC7.html) | ||
| DE68921674T2 (de) | Peptide, deren Verwendung als Immuno-Suppressanten und Verfahren zu deren Herstellung. | |
| CH615904A5 (en) | Process for the preparation of L-leucine-13-motilin | |
| DE69120397T2 (de) | Physiologisch aktive substanzen, die gut zum durchdringen biologischer membranen befähigt sind | |
| WO1981000712A1 (fr) | Peptides pharmacologiquement actifs et medicaments les contenant | |
| DE3117948A1 (de) | Anorexigene peptide | |
| EP0137339B1 (de) | Pharmakologisch aktive Peptide | |
| EP0095557B1 (de) | Polypeptide mit antagonistischen Eigenschaften gegenüber der Substanz P, Verfahren zu ihrer Herstellung, deren Verwendung und Verfahren zum Reinigen von Polypeptiden | |
| CH639941A5 (en) | Polypeptides, process for their preparation and their use | |
| DD297416A5 (de) | Verfahren zur herstellung von peptiden mit der faehigkeit, die cgmp-aktivitaet in der human-t-zellinie cem zu erhoehen und verwendung der peptide | |
| DE69120247T2 (de) | Peptidverbindungen von linksdrehenden aminosäuren und ringmolekülen, und therapeutische anwendung davon | |
| CH618960A5 (cg-RX-API-DMAC7.html) | ||
| CH654841A5 (de) | Appetitzuegelnde tripeptide und verfahren zur herstellung derselben. | |
| DE69813232T2 (de) | Wespe pompilid neuropeptide | |
| DE3873255T2 (de) | Methoden und praeparate zur vorbeugung von ulcera. | |
| HK1160778B (en) | Pharmaceutical composition comprising an analgesic peptide | |
| DE4340111A1 (de) | Tumor-Nekrose-Faktor-alpha inaktivierende Peptide | |
| CH637626A5 (en) | Process for the preparation of peptides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |