CA2005058A1 - Peptides tnf - Google Patents

Peptides tnf

Info

Publication number: CA2005058A1
Authority: CA; Canada
Prior art keywords: lys; peptide; asp; gly; glu
Prior art date: 1988-12-12
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002005058A

Other languages

English (en)

Inventor

Bernhard Schmied

Nigel Walker

Hans-Joachim Boehm

Lothar Daum

Andreas Haupt

Johann-Christian Zechel

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

1988-12-12

Filing date

1989-12-11

Publication date

1990-06-12

1989-12-11 Application filed by BASF SE filed Critical BASF SE

1990-06-12 Publication of CA2005058A1 publication Critical patent/CA2005058A1/fr

Status Abandoned legal-status Critical Current

Links

108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 59
102000004196 processed proteins & peptides Human genes 0.000 title abstract description 16
101150033527 TNF gene Proteins 0.000 title description 2
201000010099 disease Diseases 0.000 claims abstract description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 4
238000002360 preparation method Methods 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
206010061218 Inflammation Diseases 0.000 claims description 3
230000004054 inflammatory process Effects 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
238000007796 conventional method Methods 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
208000015181 infectious disease Diseases 0.000 claims description 2
230000001613 neoplastic effect Effects 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
208000023275 Autoimmune disease Diseases 0.000 claims 1
206010052779 Transplant rejections Diseases 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
210000004027 cell Anatomy 0.000 description 29
239000011347 resin Substances 0.000 description 22
229920005989 resin Polymers 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
229940024606 amino acid Drugs 0.000 description 12
239000002609 medium Substances 0.000 description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 11
125000006239 protecting group Chemical group 0.000 description 11
239000000243 solution Substances 0.000 description 11
150000001413 amino acids Chemical class 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
238000003776 cleavage reaction Methods 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
230000007017 scission Effects 0.000 description 9
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230000003013 cytotoxicity Effects 0.000 description 8
231100000135 cytotoxicity Toxicity 0.000 description 8
238000010790 dilution Methods 0.000 description 8
239000012895 dilution Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
238000004113 cell culture Methods 0.000 description 7
239000013078 crystal Substances 0.000 description 7
230000001472 cytotoxic effect Effects 0.000 description 7
108091003079 Bovine Serum Albumin Proteins 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000012894 fetal calf serum Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
-1 2-oxo-3-oxazolidinyl Chemical group 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
239000012634 fragment Substances 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
239000000126 substance Substances 0.000 description 5
DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
230000003042 antagnostic effect Effects 0.000 description 4
230000008485 antagonism Effects 0.000 description 4
231100000433 cytotoxic Toxicity 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000001963 growth medium Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
238000010079 rubber tapping Methods 0.000 description 4
102000003298 tumor necrosis factor receptor Human genes 0.000 description 4
DVBUCBXGDWWXNY-SFHVURJKSA-N (2s)-5-(diaminomethylideneamino)-2-(9h-fluoren-9-ylmethoxycarbonylamino)pentanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CCCN=C(N)N)C(O)=O)C3=CC=CC=C3C2=C1 DVBUCBXGDWWXNY-SFHVURJKSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
230000001413 cellular effect Effects 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
229960004756 ethanol Drugs 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229960002743 glutamine Drugs 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
HJJURMMMGPQIQP-DEOSSOPVSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-phenylmethoxypentanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)CC(=O)OCC1=CC=CC=C1 HJJURMMMGPQIQP-DEOSSOPVSA-N 0.000 description 2
NLPQIWFEEKQBBN-NSHDSACASA-N (2s)-4-cyclohexyloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC(=O)OC1CCCCC1 NLPQIWFEEKQBBN-NSHDSACASA-N 0.000 description 2
FDNMLANBNJDIRG-LBPRGKRZSA-N (2s)-5-cyclohexyloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCC(=O)OC1CCCCC1 FDNMLANBNJDIRG-LBPRGKRZSA-N 0.000 description 2
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
NDKDFTQNXLHCGO-UHFFFAOYSA-N 2-(9h-fluoren-9-ylmethoxycarbonylamino)acetic acid Chemical compound C1=CC=C2C(COC(=O)NCC(=O)O)C3=CC=CC=C3C2=C1 NDKDFTQNXLHCGO-UHFFFAOYSA-N 0.000 description 2
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 2
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
PECYZEOJVXMISF-UHFFFAOYSA-N 3-aminoalanine Chemical compound [NH3+]CC(N)C([O-])=O PECYZEOJVXMISF-UHFFFAOYSA-N 0.000 description 2
229960000549 4-dimethylaminophenol Drugs 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
244000228957 Ferula foetida Species 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
239000007995 HEPES buffer Substances 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
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WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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FODJWPHPWBKDON-IBGZPJMESA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CC(=O)OC(C)(C)C)C(O)=O)C3=CC=CC=C3C2=C1 FODJWPHPWBKDON-IBGZPJMESA-N 0.000 description 1
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FNQIGYRDLYROLW-UHFFFAOYSA-N 1-hydroxy-2h-1,2,3-benzotriazine Chemical compound C1=CC=C2N(O)NN=CC2=C1 FNQIGYRDLYROLW-UHFFFAOYSA-N 0.000 description 1
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KLDLRDSRCMJKGM-UHFFFAOYSA-N 3-[chloro-(2-oxo-1,3-oxazolidin-3-yl)phosphoryl]-1,3-oxazolidin-2-one Chemical compound C1COC(=O)N1P(=O)(Cl)N1CCOC1=O KLDLRDSRCMJKGM-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
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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
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XYVRXLDSCKEYES-JSGCOSHPSA-N Met-Trp Chemical compound C1=CC=C2C(C[C@H](NC(=O)[C@@H](N)CCSC)C(O)=O)=CNC2=C1 XYVRXLDSCKEYES-JSGCOSHPSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
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101100074988 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nmp-1 gene Proteins 0.000 description 1
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AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
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239000004793 Polystyrene Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
101100240664 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nmt1 gene Proteins 0.000 description 1
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KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
102000000763 Survivin Human genes 0.000 description 1
108010002687 Survivin Proteins 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
244000166490 Tetrameles nudiflora Species 0.000 description 1
241000011102 Thera 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
206010054094 Tumour necrosis Diseases 0.000 description 1
OGQICQVSFDPSEI-UHFFFAOYSA-N Zorac Chemical compound N1=CC(C(=O)OCC)=CC=C1C#CC1=CC=C(SCCC2(C)C)C2=C1 OGQICQVSFDPSEI-UHFFFAOYSA-N 0.000 description 1
239000012190 activator Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
210000004102 animal cell Anatomy 0.000 description 1
238000010171 animal model Methods 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
238000013459 approach Methods 0.000 description 1
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DQSGVVGOPRWTKI-QVFAWCHISA-N atazanavir sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 DQSGVVGOPRWTKI-QVFAWCHISA-N 0.000 description 1
229940054720 avage Drugs 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
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230000002860 competitive effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
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238000010511 deprotection reaction Methods 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
229940091249 fluoride supplement Drugs 0.000 description 1
MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
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DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
229960003692 gamma aminobutyric acid Drugs 0.000 description 1
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutanoic acid Natural products NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
238000002523 gelfiltration Methods 0.000 description 1
229960002518 gentamicin Drugs 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940097043 glucuronic acid Drugs 0.000 description 1
229960002989 glutamic acid Drugs 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
210000005260 human cell Anatomy 0.000 description 1
235000011167 hydrochloric acid Nutrition 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
108010034507 methionyltryptophan Proteins 0.000 description 1
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229940113083 morpholine Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 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
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/52—Cytokines; Lymphokines; Interferons
- C07K14/525—Tumour necrosis factor [TNF]
- 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
- A61P35/00—Antineoplastic agents
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Immunology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Gastroenterology & Hepatology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Toxicology (AREA)
Zoology (AREA)
Transplantation (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA002005058A 1988-12-12 1989-12-11 Peptides tnf Abandoned CA2005058A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP3841753.7		1988-12-12
DE3841753A DE3841753A1 (de)	1988-12-12	1988-12-12	Neue tnf-peptide

Publications (1)

Publication Number	Publication Date
CA2005058A1 true CA2005058A1 (fr)	1990-06-12

Family

ID=6368952

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002005058A Abandoned CA2005058A1 (fr)	1988-12-12	1989-12-11	Peptides tnf

Country Status (5)

Country	Link
EP (1)	EP0447435A1 (fr)
JP (1)	JPH04502314A (fr)
CA (1)	CA2005058A1 (fr)
DE (1)	DE3841753A1 (fr)
WO (1)	WO1990006943A2 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU639409B2 (en) *	1987-12-10	1993-07-29	La Jolla Cancer Research Foundation	Conformationally stabilized cell adhesion peptides
US5827821A (en)	1987-12-10	1998-10-27	The Burnham Institute	Conformationally stabilized cell adhesion peptides
US5686569A (en) *	1989-06-16	1997-11-11	Cor Therapeutics, Inc.	Platelet aggregation inhibitors
US5807828A (en) *	1989-06-16	1998-09-15	Cor Therapeutics, Inc.	Platelet aggregation inhibitors
DE69126871T2 (de) *	1990-04-06	1998-03-12	Jolla Cancer Res Found	Verfahren und verbindung zur behandlung von thrombose
US5648330A (en) *	1990-04-06	1997-07-15	La Jolla Cancer Research Foundation	Method and composition for treating vascular graft occlusion
US6521594B1 (en)	1990-04-06	2003-02-18	La Jolla Cancer Research Foundation	Method and composition for treating thrombosis
US5612311A (en) *	1990-04-06	1997-03-18	La Jolla Cancer Research Foundation	Method and composition for treating thrombosis
US5780303A (en) *	1990-04-06	1998-07-14	La Jolla Cancer Research Foundation	Method and composition for treating thrombosis
CA2106314A1 (fr) *	1991-04-05	1992-10-06	John P. Burnier	Inhibiteurs de l'agregation plaquettaire hautement specifiques du gpiibiiia
US6107273A (en) *	1995-01-24	2000-08-22	Thomas Jefferson University	Tumor necrosis factor inhibitors
CN1052464C (zh) *	1995-11-03	2000-05-17	康宁股份有限公司	抗氢致衰减的光纤

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3781263T2 (de) *	1986-12-15	1993-04-08	Inst Nat Sante Rech Med	Peptid-derivate und deren verwendung in der therapie.
AU3149289A (en) *	1988-03-18	1989-09-21	Rockefeller University, The	Method and agent for inhibiting the binding of human polymorphonuclear leukocytes to endothelium and compositions therefor

1988
- 1988-12-12 DE DE3841753A patent/DE3841753A1/de not_active Withdrawn
1989
- 1989-12-02 EP EP90900176A patent/EP0447435A1/fr not_active Withdrawn
- 1989-12-02 JP JP2501008A patent/JPH04502314A/ja active Pending
- 1989-12-02 WO PCT/EP1989/001470 patent/WO1990006943A2/fr not_active Ceased
- 1989-12-11 CA CA002005058A patent/CA2005058A1/fr not_active Abandoned

Also Published As

Publication number	Publication date
JPH04502314A (ja)	1992-04-23
DE3841753A1 (de)	1990-06-13
WO1990006943A2 (fr)	1990-06-28
EP0447435A1 (fr)	1991-09-25
WO1990006943A3 (fr)	1990-08-09

Legal Events

Date	Code	Title	Description
1993-06-13	FZDE	Dead

Publication	Publication Date	Title
RU2132334C1 (ru)	1999-06-27	Аналог долостатина
CN101678213B (zh)	2013-11-06	环肽cxcr4拮抗剂
JPH08511167A (ja)	1996-11-26	ケモカインの生物学的活性の強化法
JP3523253B2 (ja)	2004-04-26	ドラスタチン誘導体
EP2161037A2 (fr)	2010-03-10	Conjugués de Camptothecin-Somatostatin
US20240209023A1 (en)	2024-06-27	Peptide compound, application thereof and composition containing same
US5231082A (en)	1993-07-27	Cyclic peptide with anti-metastasis activity
CA2005051A1 (fr)	1990-06-12	Peptides tnf
CA2005050A1 (fr)	1990-06-12	Peptides tnf
US4473555A (en)	1984-09-25	Nona- and dodecapeptides for augmenting natural killer cell activity
JPH04502314A (ja)	1992-04-23	新規ｔｎｆペプチド
JPH04502157A (ja)	1992-04-16	新規ｔｎｆペプチド
CA2005060A1 (fr)	1990-06-12	Peptides tnf
CA2376506A1 (fr)	2000-12-14	Antagonistes des recepteurs de la somatostatine et de la neuromedine b
CA2005052A1 (fr)	1990-06-12	Peptides tnf
CA2005061A1 (fr)	1990-06-12	Peptides tnf
CA2005281A1 (fr)	1990-06-12	Peptides tnf
US5179082A (en)	1993-01-12	Method for blocking platelet adhesion to collagen
CA2005056A1 (fr)	1990-06-12	Peptides tnf
CA2005057A1 (fr)	1990-06-12	Peptides tnf
WO1993006128A1 (fr)	1993-04-01	Peptides antagonistes du facteur de necrose tumorale
JPS6330499A (ja)	1988-02-09	オピオイドペプチド・ポリペプチド複合体
WO1992011285A1 (fr)	1992-07-09	Nouveaux peptides constituant des facteurs de necrose tumorale
DE4041189A1 (de)	1992-06-25	Neue-tnf-peptide