BG60621B1 - Нов полипептид и анти-hiv лекарство, получено от него - Google Patents
Нов полипептид и анти-hiv лекарство, получено от него Download PDFInfo
- Publication number
- BG60621B1 BG60621B1 BG96323A BG9632392A BG60621B1 BG 60621 B1 BG60621 B1 BG 60621B1 BG 96323 A BG96323 A BG 96323A BG 9632392 A BG9632392 A BG 9632392A BG 60621 B1 BG60621 B1 BG 60621B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- hours
- residue
- cys
- arginine
- cysteine
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 66
- 229920001184 polypeptide Polymers 0.000 title claims abstract description 51
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract description 51
- 230000036436 anti-hiv Effects 0.000 title claims abstract description 10
- 239000003814 drug Substances 0.000 title description 7
- 239000000126 substance Substances 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 20
- 235000001014 amino acid Nutrition 0.000 claims description 18
- 229940024606 amino acid Drugs 0.000 claims description 18
- 150000001413 amino acids Chemical class 0.000 claims description 17
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 14
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 239000004475 Arginine Substances 0.000 claims description 12
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 12
- 235000018417 cysteine Nutrition 0.000 claims description 10
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 9
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 8
- 125000000539 amino acid group Chemical group 0.000 claims description 8
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 6
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 5
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 5
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 5
- 239000004472 Lysine Substances 0.000 claims description 5
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 4
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 4
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 4
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 4
- 235000004279 alanine Nutrition 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 4
- 229960000310 isoleucine Drugs 0.000 claims description 4
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims description 4
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 claims description 4
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 4
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 4
- 239000004474 valine Substances 0.000 claims description 4
- OIXLLKLZKCBCPS-RZVRUWJTSA-N (2s)-2-azanyl-5-[bis(azanyl)methylideneamino]pentanoic acid Chemical group OC(=O)[C@@H](N)CCCNC(N)=N.OC(=O)[C@@H](N)CCCNC(N)=N OIXLLKLZKCBCPS-RZVRUWJTSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 2
- 235000005772 leucine Nutrition 0.000 claims 3
- 235000014705 isoleucine Nutrition 0.000 claims 2
- 235000004400 serine Nutrition 0.000 claims 2
- 235000014393 valine Nutrition 0.000 claims 2
- 230000000840 anti-viral effect Effects 0.000 abstract description 11
- 239000004480 active ingredient Substances 0.000 abstract 2
- 241000700605 Viruses Species 0.000 abstract 1
- 230000007812 deficiency Effects 0.000 abstract 1
- 239000011347 resin Substances 0.000 description 26
- 229920005989 resin Polymers 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 238000000034 method Methods 0.000 description 20
- -1 t-butylthio Chemical group 0.000 description 16
- 241000725303 Human immunodeficiency virus Species 0.000 description 13
- 125000006239 protecting group Chemical group 0.000 description 12
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 7
- 238000006482 condensation reaction Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002158 endotoxin Substances 0.000 description 6
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 5
- 241000239204 Xiphosura Species 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- CMWYAOXYQATXSI-UHFFFAOYSA-N n,n-dimethylformamide;piperidine Chemical compound CN(C)C=O.C1CCNCC1 CMWYAOXYQATXSI-UHFFFAOYSA-N 0.000 description 5
- WTKQMHWYSBWUBE-UHFFFAOYSA-N (3-nitropyridin-2-yl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CN=C1SCl WTKQMHWYSBWUBE-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000003275 alpha amino acid group Chemical group 0.000 description 4
- 230000003013 cytotoxicity Effects 0.000 description 4
- 231100000135 cytotoxicity Toxicity 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 101100042788 Caenorhabditis elegans him-1 gene Proteins 0.000 description 3
- 241000238424 Crustacea Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 3
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- SHDMMLFAFLZUEV-UHFFFAOYSA-N n-methyl-1,1-diphenylmethanamine Chemical compound C=1C=CC=CC=1C(NC)C1=CC=CC=C1 SHDMMLFAFLZUEV-UHFFFAOYSA-N 0.000 description 3
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 3
- 229960002555 zidovudine Drugs 0.000 description 3
- VVQIIIAZJXTLRE-QMMMGPOBSA-N (2s)-2-amino-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid Chemical compound CC(C)(C)OC(=O)NCCCC[C@H](N)C(O)=O VVQIIIAZJXTLRE-QMMMGPOBSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 241000239205 Merostomata Species 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 238000005273 aeration Methods 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 229940124411 anti-hiv antiviral agent Drugs 0.000 description 2
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000002523 gelfiltration Methods 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 210000000582 semen Anatomy 0.000 description 2
- 238000010532 solid phase synthesis reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- GWHBNBQDTRNFIE-UHFFFAOYSA-N 1,1-dichloroethane;2,2,2-trifluoroacetic acid Chemical compound CC(Cl)Cl.OC(=O)C(F)(F)F GWHBNBQDTRNFIE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XFZYPCNLVHSQTG-UHFFFAOYSA-N 2,2,5,7,8-pentamethyl-3,4-dihydrochromene Chemical compound C1CC(C)(C)OC2=C(C)C(C)=CC(C)=C21 XFZYPCNLVHSQTG-UHFFFAOYSA-N 0.000 description 1
- WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 1
- YVOOPGWEIRIUOX-UHFFFAOYSA-N 2-azanyl-3-sulfanyl-propanoic acid Chemical compound SCC(N)C(O)=O.SCC(N)C(O)=O YVOOPGWEIRIUOX-UHFFFAOYSA-N 0.000 description 1
- 201000002569 3-methylglutaconic aciduria type 5 Diseases 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- NZQFXJKVNUZYAG-BPUTZDHNSA-N Arg-Trp-Cys Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@H](CCCN=C(N)N)N)C(=O)N[C@@H](CS)C(O)=O)=CNC2=C1 NZQFXJKVNUZYAG-BPUTZDHNSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 241000239216 Carcinoscorpius Species 0.000 description 1
- 241001529572 Chaceon affinis Species 0.000 description 1
- VCBRBUKGTWLJOB-UHFFFAOYSA-N Chloranocryl Chemical compound CC(=C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 VCBRBUKGTWLJOB-UHFFFAOYSA-N 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-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
- 102000002704 Leucyl aminopeptidase Human genes 0.000 description 1
- 108010004098 Leucyl aminopeptidase Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000239222 Tachypleus Species 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
- 208000036142 Viral infection Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 108010062796 arginyllysine Proteins 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 108010069495 cysteinyltyrosine Proteins 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 210000003677 hemocyte Anatomy 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229920006008 lipopolysaccharide Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- KCCSOSBUHIQUOT-UHFFFAOYSA-N n,n'-di(propan-2-yl)methanediimine;1-hydroxybenzotriazole Chemical compound CC(C)N=C=NC(C)C.C1=CC=C2N(O)N=NC2=C1 KCCSOSBUHIQUOT-UHFFFAOYSA-N 0.000 description 1
- VEFCXXLAPLJBFG-UHFFFAOYSA-N n,n-dimethoxy-1,1-diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N(OC)OC)C1=CC=CC=C1 VEFCXXLAPLJBFG-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229940073020 nitrol Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- AWEMSNRRIVQFLI-UHFFFAOYSA-N sulfonylmethanesulfonic acid Chemical compound S(=O)(=O)=CS(=O)(=O)O AWEMSNRRIVQFLI-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- AIDS & HIV (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP23892290 | 1990-09-11 | ||
| PCT/JP1991/001201 WO1992004374A1 (en) | 1990-09-11 | 1991-09-10 | Novel polypeptide and anti-hiv drug prepared therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG96323A BG96323A (bg) | 1993-12-24 |
| BG60621B1 true BG60621B1 (bg) | 1995-10-31 |
Family
ID=17037269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG96323A BG60621B1 (bg) | 1990-09-11 | 1992-05-11 | Нов полипептид и анти-hiv лекарство, получено от него |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5571892A (da) |
| EP (1) | EP0502198B1 (da) |
| JP (1) | JP3178835B2 (da) |
| KR (1) | KR0184604B1 (da) |
| AT (1) | ATE132163T1 (da) |
| AU (1) | AU638606B2 (da) |
| BG (1) | BG60621B1 (da) |
| BR (1) | BR9105902A (da) |
| CA (1) | CA2068327C (da) |
| CZ (1) | CZ280870B6 (da) |
| DE (1) | DE69115878T2 (da) |
| DK (1) | DK0502198T3 (da) |
| ES (1) | ES2081491T3 (da) |
| FI (1) | FI922044A0 (da) |
| GR (1) | GR3018879T3 (da) |
| HU (1) | HUT61579A (da) |
| NO (1) | NO921829L (da) |
| OA (1) | OA10030A (da) |
| RO (1) | RO109653B1 (da) |
| RU (1) | RU2073685C1 (da) |
| WO (1) | WO1992004374A1 (da) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3266311B2 (ja) * | 1991-05-02 | 2002-03-18 | 生化学工業株式会社 | 新規ポリペプチドおよびこれを用いる抗ｈｉｖ剤 |
| JP3361830B2 (ja) * | 1992-03-30 | 2003-01-07 | 生化学工業株式会社 | 抗菌性組成物及びそれを有効成分とする薬剤 |
| CN1038841C (zh) * | 1993-10-14 | 1998-06-24 | 生化学工业株式会社 | 新型多肽以及由其制备的抗人类免疫缺陷病毒制剂 |
| WO1998016555A1 (fr) * | 1996-10-15 | 1998-04-23 | Seikagaku Corporation | Sels de metaux de transition d'un polypeptide et procede d'accroissement de l'activite anti-vih de ce polypeptide |
| AU6518698A (en) * | 1997-03-28 | 1998-10-22 | Seikagaku Corporation | Novel anti-hiv complexes and medicinal compositions |
| KR20020019126A (ko) * | 1999-08-09 | 2002-03-09 | 트리펩 아베 | 트리펩티드를 함유하는 약학 조성물 |
| US6593455B2 (en) * | 2001-08-24 | 2003-07-15 | Tripep Ab | Tripeptide amides that block viral infectivity and methods of use thereof |
| WO2003024995A1 (en) * | 2001-09-19 | 2003-03-27 | Tripep Ab | Molecules that block viral infectivity and methods of use thereof |
| JP2006518373A (ja) * | 2003-02-21 | 2006-08-10 | トリペップ アクチ ボラゲット | Ｈｉｖ複製を抑制するためのグリシンアミド誘導体 |
| US20050096319A1 (en) * | 2003-02-21 | 2005-05-05 | Balzarini Jan M.R. | Identification of compounds that inhibit replication of human immunodeficiency virus |
| USD807457S1 (en) | 2016-07-20 | 2018-01-09 | Razor Usa Llc | Two wheeled board |
| USD803963S1 (en) | 2016-07-20 | 2017-11-28 | Razor Usa Llc | Two wheeled board |
| USD840872S1 (en) | 2016-07-20 | 2019-02-19 | Razor Usa Llc | Two wheeled board |
| USD837323S1 (en) | 2018-01-03 | 2019-01-01 | Razor Usa Llc | Two wheeled board |
| USD941948S1 (en) | 2016-07-20 | 2022-01-25 | Razor Usa Llc | Two wheeled board |
| EP3728009A4 (en) | 2017-12-22 | 2021-09-29 | Razor USA LLC | ELECTRIC BALANCING VEHICLES |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1337781C (en) * | 1987-08-21 | 1995-12-19 | Takanori Nakamura | Polypeptide from horseshoe crab exhibiting affinity for lipopolysaccharide and method of preparation |
| JP2641742B2 (ja) * | 1988-08-18 | 1997-08-20 | マルハ株式会社 | 新規ペプチド及び抗菌剤 |
| JP2641744B2 (ja) * | 1988-08-18 | 1997-08-20 | マルハ株式会社 | 新規ペプチド及び抗菌剤 |
| JP2798711B2 (ja) * | 1988-09-26 | 1998-09-17 | 生化学工業株式会社 | ポリペプチド系抗ウィルス剤 |
| JP3266311B2 (ja) * | 1991-05-02 | 2002-03-18 | 生化学工業株式会社 | 新規ポリペプチドおよびこれを用いる抗ｈｉｖ剤 |
| JP2500194B2 (ja) | 1993-08-10 | 1996-05-29 | 株式会社ヴァンドームヤマダ | 商品発注システム |
-
1991
- 1991-09-10 JP JP51480791A patent/JP3178835B2/ja not_active Expired - Fee Related
- 1991-09-10 CA CA002068327A patent/CA2068327C/en not_active Expired - Fee Related
- 1991-09-10 AT AT91915604T patent/ATE132163T1/de not_active IP Right Cessation
- 1991-09-10 DK DK91915604.2T patent/DK0502198T3/da active
- 1991-09-10 HU HU9201540A patent/HUT61579A/hu unknown
- 1991-09-10 WO PCT/JP1991/001201 patent/WO1992004374A1/ja active IP Right Grant
- 1991-09-10 BR BR9105902A patent/BR9105902A/pt not_active Application Discontinuation
- 1991-09-10 AU AU84480/91A patent/AU638606B2/en not_active Ceased
- 1991-09-10 KR KR1019920701101A patent/KR0184604B1/ko not_active IP Right Cessation
- 1991-09-10 DE DE69115878T patent/DE69115878T2/de not_active Expired - Fee Related
- 1991-09-10 US US07/856,026 patent/US5571892A/en not_active Expired - Fee Related
- 1991-09-10 EP EP91915604A patent/EP0502198B1/en not_active Expired - Lifetime
- 1991-09-10 RO RO92-200638A patent/RO109653B1/ro unknown
- 1991-09-10 ES ES91915604T patent/ES2081491T3/es not_active Expired - Lifetime
- 1991-09-10 RU SU915052258A patent/RU2073685C1/ru not_active IP Right Cessation
-
1992
- 1992-05-06 FI FI922044A patent/FI922044A0/fi unknown
- 1992-05-07 CZ CS921394A patent/CZ280870B6/cs not_active IP Right Cessation
- 1992-05-08 NO NO92921829A patent/NO921829L/no not_active Application Discontinuation
- 1992-05-11 BG BG96323A patent/BG60621B1/bg unknown
- 1992-05-11 OA OA60206A patent/OA10030A/en unknown
-
1996
- 1996-02-01 GR GR960400273T patent/GR3018879T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU8448091A (en) | 1992-03-30 |
| AU638606B2 (en) | 1993-07-01 |
| EP0502198A4 (en) | 1993-05-05 |
| CA2068327A1 (en) | 1992-03-12 |
| JP3178835B2 (ja) | 2001-06-25 |
| CS139492A3 (en) | 1992-09-16 |
| US5571892A (en) | 1996-11-05 |
| NO921829D0 (no) | 1992-05-08 |
| EP0502198A1 (en) | 1992-09-09 |
| RU2073685C1 (ru) | 1997-02-20 |
| FI922044A (fi) | 1992-05-06 |
| CZ280870B6 (cs) | 1996-04-17 |
| ATE132163T1 (de) | 1996-01-15 |
| KR0184604B1 (ko) | 1999-05-01 |
| ES2081491T3 (es) | 1996-03-16 |
| HU9201540D0 (en) | 1992-08-28 |
| BG96323A (bg) | 1993-12-24 |
| CA2068327C (en) | 2002-01-01 |
| WO1992004374A1 (en) | 1992-03-19 |
| EP0502198B1 (en) | 1995-12-27 |
| OA10030A (en) | 1996-10-14 |
| HUT61579A (en) | 1993-01-28 |
| DK0502198T3 (da) | 1996-01-29 |
| DE69115878D1 (de) | 1996-02-08 |
| GR3018879T3 (en) | 1996-05-31 |
| DE69115878T2 (de) | 1996-06-05 |
| RO109653B1 (ro) | 1995-04-28 |
| BR9105902A (pt) | 1994-06-28 |
| NO921829L (no) | 1992-07-09 |
| FI922044A0 (fi) | 1992-05-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3266311B2 (ja) | 新規ポリペプチドおよびこれを用いる抗ｈｉｖ剤 | |
| BG60621B1 (bg) | Нов полипептид и анти-hiv лекарство, получено от него | |
| HU217442B (hu) | Polipeptidek és ezeket tartalmazó HIV-ellenes hatású gyógyászati készítmények | |
| EP1179537B1 (en) | Solid phase peptide synthesis method | |
| FI92708C (fi) | Menetelmä uuden lääkeaineena käyttökelpoisen polypeptidin valmistamiseksi | |
| RU2083589C1 (ru) | Полипептиды или их соли и фармацевтическая композиция | |
| Limal et al. | Solid‐phase synthesis and on‐resin cyclization of a disulfide bond peptide and lactam analogues corresponding to the major antigenic site of HIV gp41 protein | |
| Albericio et al. | Solid phase synthesis and HPLC purification of the protected 1-12 sequence of apamin for rapid synthesis of apamin analogues differing in the C-terminal region | |
| CN108047323B (zh) | 一种固相片段法合成GpTx-1及其类似物和合成方法 | |
| CA2155872C (en) | Oxytocin antagonist | |
| JPS60161999A (ja) | ペプチド | |
| CN110981939A (zh) | 一种普利卡那肽的制备方法 | |
| CN1120174C (zh) | 海洋芋螺镇痛多肽的制备方法 | |
| JPH05500962A (ja) | 硫酸エステル基を有するヘキサペプチド | |
| JPH02167230A (ja) | ポリペプチド系抗ウィルス剤 | |
| JPS6330499A (ja) | オピオイドペプチド・ポリペプチド複合体 | |
| JPS6168499A (ja) | 新規ペプチド | |
| JPS6110598A (ja) | ペプチド化合物 | |
| JPH07228600A (ja) | カルシトニン誘導体 |