CN1033633A - 新型同多肽及其制备方法 - Google Patents

新型同多肽及其制备方法 Download PDF

Info

Publication number: CN1033633A
Authority: CN; China
Prior art keywords: formula; salt; group; compound; monomer
Prior art date: 1987-10-21
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.): Pending

Application number

CN88107253A

Other languages

English (en)

Chinese (zh)

Inventor

吉拉·索克恩

厄恩·泰伊克

贝拉·索恩德

卡罗利·莱平斯

里查德·加布詹泽

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.)

Institute Of Plant Protection Hungarian Academy Of Sciences

Magyar Tudomanyos Akademia Kutatas es Szervezetelemzo Intezete

Original Assignee

Institute Of Plant Protection Hungarian Academy Of Sciences

Magyar Tudomanyos Akademia Kutatas es Szervezetelemzo Intezete

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.)

1987-10-21

Filing date

1988-10-20

Publication date

1989-07-05

1988-10-20 Application filed by Institute Of Plant Protection Hungarian Academy Of Sciences, Magyar Tudomanyos Akademia Kutatas es Szervezetelemzo Intezete filed Critical Institute Of Plant Protection Hungarian Academy Of Sciences

1989-07-05 Publication of CN1033633A publication Critical patent/CN1033633A/zh

Status Pending legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 36
150000001875 compounds Chemical class 0.000 claims abstract description 40
150000003839 salts Chemical class 0.000 claims abstract description 30
230000000840 anti-viral effect Effects 0.000 claims abstract description 8
230000000259 anti-tumor effect Effects 0.000 claims abstract description 6
238000000034 method Methods 0.000 claims description 65
206010028980 Neoplasm Diseases 0.000 claims description 41
-1 Amino protecting group Chemical group 0.000 claims description 29
230000000694 effects Effects 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
238000006068 polycondensation reaction Methods 0.000 claims description 15
239000000178 monomer Substances 0.000 claims description 13
239000003513 alkali Substances 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 12
230000008878 coupling Effects 0.000 claims description 12
238000010168 coupling process Methods 0.000 claims description 12
238000005859 coupling reaction Methods 0.000 claims description 12
150000002148 esters Chemical group 0.000 claims description 12
QKEWQOJCHPFEAF-UHFFFAOYSA-N 3,6-diaminohexanoic acid Chemical compound NCCCC(N)CC(O)=O QKEWQOJCHPFEAF-UHFFFAOYSA-N 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000008064 anhydrides Chemical class 0.000 claims description 7
125000006239 protecting group Chemical group 0.000 claims description 7
239000002994 raw material Substances 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
230000004048 modification Effects 0.000 claims description 6
238000012986 modification Methods 0.000 claims description 6
150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 6
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
AHLPHDHHMVZTML-UHFFFAOYSA-N Ornithine Chemical compound NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 4
230000008859 change Effects 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
239000013543 active substance Substances 0.000 claims description 3
230000001737 promoting effect Effects 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 2
230000000996 additive effect Effects 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical class CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 claims 1
DDMUWSISECXMAB-COBSHVIPSA-N C(=O)(OC(C)(C)C)C([C@@H](N)C(=O)O)CCN Chemical compound C(=O)(OC(C)(C)C)C([C@@H](N)C(=O)O)CCN DDMUWSISECXMAB-COBSHVIPSA-N 0.000 claims 1
RIPYPEKAEQSEPG-UHFFFAOYSA-N C(=O)O.C(C(C)C)Cl Chemical compound C(=O)O.C(C(C)C)Cl RIPYPEKAEQSEPG-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
201000011510 cancer Diseases 0.000 claims 1
229920006395 saturated elastomer Polymers 0.000 claims 1
230000009466 transformation Effects 0.000 claims 1
241001465754 Metazoa Species 0.000 description 36
239000000243 solution Substances 0.000 description 25
239000000126 substance Substances 0.000 description 25
210000004027 cell Anatomy 0.000 description 22
238000011081 inoculation Methods 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
241000699666 Mus <mouse, genus> Species 0.000 description 15
238000007912 intraperitoneal administration Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
238000012360 testing method Methods 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
230000004071 biological effect Effects 0.000 description 12
210000004881 tumor cell Anatomy 0.000 description 12
108090000765 processed proteins & peptides Proteins 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
206010003445 Ascites Diseases 0.000 description 9
241000196324 Embryophyta Species 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
239000002585 base Substances 0.000 description 9
230000003203 everyday effect Effects 0.000 description 9
206010020718 hyperplasia Diseases 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
150000002431 hydrogen Chemical class 0.000 description 8
239000000463 material Substances 0.000 description 8
108010016626 Dipeptides Proteins 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
241000723873 Tobacco mosaic virus Species 0.000 description 7
210000004072 lung Anatomy 0.000 description 7
239000011521 glass Substances 0.000 description 6
239000003999 initiator Substances 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 5
239000000872 buffer Substances 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
238000009826 distribution Methods 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
229960003104 ornithine Drugs 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
238000012545 processing Methods 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
230000006340 racemization Effects 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 4
206010027457 Metastases to liver Diseases 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
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
230000004913 activation Effects 0.000 description 4
150000001413 amino acids Chemical class 0.000 description 4
230000008901 benefit Effects 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000005897 peptide coupling reaction Methods 0.000 description 4
229920000656 polylysine Polymers 0.000 description 4
239000000523 sample Substances 0.000 description 4
210000000952 spleen Anatomy 0.000 description 4
239000003826 tablet Substances 0.000 description 4
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
235000002637 Nicotiana tabacum Nutrition 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241000700605 Viruses Species 0.000 description 3
230000009471 action Effects 0.000 description 3
235000010443 alginic acid Nutrition 0.000 description 3
229920000615 alginic acid Polymers 0.000 description 3
239000012752 auxiliary agent Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
230000004663 cell proliferation Effects 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000000824 cytostatic agent Substances 0.000 description 3
230000001085 cytostatic effect Effects 0.000 description 3
238000001514 detection method Methods 0.000 description 3
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
239000008298 dragée Substances 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
208000020816 lung neoplasm Diseases 0.000 description 3
208000037841 lung tumor Diseases 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
210000003205 muscle Anatomy 0.000 description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
239000002953 phosphate buffered saline Substances 0.000 description 3
239000002504 physiological saline solution Substances 0.000 description 3
229920000729 poly(L-lysine) polymer Polymers 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
230000008569 process Effects 0.000 description 3
102000004196 processed proteins & peptides Human genes 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000004904 shortening Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000010189 synthetic method Methods 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
230000003612 virological effect Effects 0.000 description 3
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
125000006847 BOC protecting group Chemical group 0.000 description 2
201000009030 Carcinoma Diseases 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 2
208000031637 Erythroblastic Acute Leukemia Diseases 0.000 description 2
208000036566 Erythroleukaemia Diseases 0.000 description 2
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
239000004472 Lysine Substances 0.000 description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
206010027476 Metastases Diseases 0.000 description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
241000208125 Nicotiana Species 0.000 description 2
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
208000021841 acute erythroid leukemia Diseases 0.000 description 2
239000000783 alginic acid Substances 0.000 description 2
229960001126 alginic acid Drugs 0.000 description 2
150000004781 alginic acids Chemical class 0.000 description 2
238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000004113 cell culture Methods 0.000 description 2
238000011097 chromatography purification Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000013016 damping Methods 0.000 description 2
230000002939 deleterious effect Effects 0.000 description 2
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000012530 fluid Substances 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
230000002045 lasting effect Effects 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229930182817 methionine Natural products 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
230000000050 nutritive effect Effects 0.000 description 2
238000000711 polarimetry Methods 0.000 description 2
229920001184 polypeptide Polymers 0.000 description 2
230000001376 precipitating effect Effects 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
RWLXSTFQMCGJER-JTQLQIEISA-N (4-nitrophenyl) (2s)-2-amino-4-methylsulfanylbutanoate Chemical compound CSCC[C@H](N)C(=O)OC1=CC=C([N+]([O-])=O)C=C1 RWLXSTFQMCGJER-JTQLQIEISA-N 0.000 description 1
HRYZPBSOAMTFEL-UHFFFAOYSA-N 1,3-diazinane-2,4,6-trione;sodium Chemical compound [Na].O=C1CC(=O)NC(=O)N1 HRYZPBSOAMTFEL-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
VULSXQYFUHKBAN-UHFFFAOYSA-N 2-azaniumyl-5-(phenylmethoxycarbonylamino)pentanoate Chemical compound OC(=O)C(N)CCCNC(=O)OCC1=CC=CC=C1 VULSXQYFUHKBAN-UHFFFAOYSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
GMVPRGQOIOIIMI-DODZYUBVSA-N 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DODZYUBVSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
238000011765 DBA/2 mouse Methods 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
108060003951 Immunoglobulin Proteins 0.000 description 1
102000014150 Interferons Human genes 0.000 description 1
108010050904 Interferons Proteins 0.000 description 1
PECYZEOJVXMISF-UHFFFAOYSA-N L-DAPA Natural products [NH3+]CC(N)C([O-])=O PECYZEOJVXMISF-UHFFFAOYSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
229930064664 L-arginine Natural products 0.000 description 1
235000014852 L-arginine Nutrition 0.000 description 1
BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 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
229930195722 L-methionine Natural products 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
201000007224 Myeloproliferative neoplasm Diseases 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
108010039918 Polylysine Proteins 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
101710093543 Probable non-specific lipid-transfer protein Proteins 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
241001655322 Streptomycetales Species 0.000 description 1
240000006474 Theobroma bicolor Species 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
229940072056 alginate Drugs 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000002001 anti-metastasis Effects 0.000 description 1
230000002155 anti-virotic effect Effects 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
239000000305 astragalus gummifer gum Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
244000309466 calf Species 0.000 description 1
238000011088 calibration curve Methods 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
210000002421 cell wall Anatomy 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000002508 compound effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
229960005215 dichloroacetic acid Drugs 0.000 description 1
UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
238000002224 dissection Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
238000000760 immunoelectrophoresis Methods 0.000 description 1
102000018358 immunoglobulin Human genes 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
229940079322 interferon Drugs 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
238000001155 isoelectric focusing Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
210000002414 leg Anatomy 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
210000003141 lower extremity Anatomy 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
238000001819 mass spectrum Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
230000007483 microbial process Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229940126701 oral medication Drugs 0.000 description 1
238000004816 paper chromatography Methods 0.000 description 1
238000002161 passivation Methods 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
108010091575 poly-delta-L-ornithine Proteins 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
239000003910 polypeptide antibiotic agent Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000012207 quantitative assay Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
210000000689 upper leg Anatomy 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
238000005406 washing Methods 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
- C07K7/02—Linear peptides containing at least one abnormal peptide link
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/10—Alpha-amino-carboxylic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Communicable Diseases (AREA)
Genetics & Genomics (AREA)
Oncology (AREA)
Epidemiology (AREA)
Polymers & Plastics (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Virology (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Polyamides (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Compositions Of Macromolecular Compounds (AREA)

CN88107253A 1987-10-21 1988-10-20 新型同多肽及其制备方法 Pending CN1033633A (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU4723/87		1987-10-21
HU874723A HU202553B (en)	1987-10-21	1987-10-21	Process for producing isopolypeptides composed of diamino monokarboxylic acids and pharmaceutical compositions comprising same, as well as plant protective comprising polyisolysine

Publications (1)

Publication Number	Publication Date
CN1033633A true CN1033633A (zh)	1989-07-05

Family

ID=10968769

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN88107253A Pending CN1033633A (zh)	1987-10-21	1988-10-20	新型同多肽及其制备方法

Country Status (13)

Country	Link
JP (1)	JPH02124861A (fi)
KR (1)	KR890006670A (fi)
CN (1)	CN1033633A (fi)
DE (1)	DE3835962A1 (fi)
DK (1)	DK585988A (fi)
ES (1)	ES2012559A6 (fi)
FI (1)	FI884890A (fi)
FR (1)	FR2622195A1 (fi)
GB (2)	GB8824278D0 (fi)
HU (1)	HU202553B (fi)
IT (1)	IT1230584B (fi)
NL (1)	NL8802604A (fi)
SE (1)	SE8803765L (fi)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101234122B (zh) *	2008-03-03	2010-06-30	中国科学院化学研究所	多聚赖氨酸的新用途

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0220271A (ja) *	1988-07-07	1990-01-23	Chisso Corp	食品保存用エタノール製剤
AU695290B2 (en) *	1993-10-05	1998-08-13	Unilever Plc	Improvements relating to antibacterial compositions
HUP9902217A3 (en)	1999-06-29	2002-07-29	Szegoe Peter	Polycation based bioconjugates and process for producing thereof
JP5100977B2 (ja) *	2005-04-18	2012-12-19	Ｊｎｃ株式会社	ポリ−γ−Ｌ−ジアミノ酪酸及びその塩
GB201409451D0 (en)	2014-05-28	2014-07-09	Ipabc Ltd	Antimicrobial preparations, methods for preparing the same and uses thereof to combat microorganisms

1987
- 1987-10-21 HU HU874723A patent/HU202553B/hu unknown
1988
- 1988-10-17 GB GB888824278A patent/GB8824278D0/en active Pending
- 1988-10-20 CN CN88107253A patent/CN1033633A/zh active Pending
- 1988-10-21 DE DE3835962A patent/DE3835962A1/de not_active Withdrawn
- 1988-10-21 DK DK585988A patent/DK585988A/da not_active Application Discontinuation
- 1988-10-21 NL NL8802604A patent/NL8802604A/nl not_active Application Discontinuation
- 1988-10-21 GB GB8824694A patent/GB2212810A/en not_active Withdrawn
- 1988-10-21 FI FI884890A patent/FI884890A/fi not_active Application Discontinuation
- 1988-10-21 IT IT8822389A patent/IT1230584B/it active
- 1988-10-21 FR FR8813807A patent/FR2622195A1/fr not_active Withdrawn
- 1988-10-21 KR KR1019880013784A patent/KR890006670A/ko not_active Application Discontinuation
- 1988-10-21 ES ES8803218A patent/ES2012559A6/es not_active Expired - Lifetime
- 1988-10-21 JP JP63264255A patent/JPH02124861A/ja active Pending
- 1988-10-21 SE SE8803765A patent/SE8803765L/ not_active Application Discontinuation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101234122B (zh) *	2008-03-03	2010-06-30	中国科学院化学研究所	多聚赖氨酸的新用途

Also Published As

Publication number	Publication date
JPH02124861A (ja)	1990-05-14
SE8803765D0 (sv)	1988-10-21
GB2212810A (en)	1989-08-02
GB8824694D0 (en)	1988-11-30
KR890006670A (ko)	1989-06-15
IT1230584B (it)	1991-10-28
FI884890A0 (fi)	1988-10-21
DE3835962A1 (de)	1989-06-01
ES2012559A6 (es)	1990-04-01
IT8822389A0 (it)	1988-10-21
DK585988D0 (da)	1988-10-21
SE8803765L (sv)	1989-04-22
FI884890A (fi)	1989-04-22
GB8824278D0 (en)	1988-11-23
HUT48279A (en)	1989-05-29
DK585988A (da)	1989-04-22
FR2622195A1 (fr)	1989-04-28
HU202553B (en)	1991-03-28
NL8802604A (nl)	1989-05-16

Legal Events

Date	Code	Title
1989-07-05	C06	Publication
1989-07-05	PB01	Publication
1991-08-07	C01	Deemed withdrawal of patent application (patent law 1993)
1991-08-07	WD01	Invention patent application deemed withdrawn after publication

Publication	Publication Date	Title
CN1027265C (zh)	1995-01-04	水溶性喜树碱类似物的制备方法
CN1073560C (zh)	2001-10-24	环缩酚酸肽pf1022衍生物
CN86104185A (zh)	1987-04-08	N-(2-氨基酰氨基-2-去氧-己糖基)-酰胺类、氨基甲酸酯类和一脲类的制备工艺及其医药用途
CN1063110A (zh)	1992-07-29	抗菌素ge2270因子的酰胺类化合物衍生物
CN1157618A (zh)	1997-08-20	有免疫调节活性的新的取代嘌呤基衍生物
CN1079836C (zh)	2002-02-27	通过发酵生产l-赖氨酸及l-谷氨酸的方法
CN1282316A (zh)	2001-01-31	用作神经氨酸酶抑制剂的取代环戊烷和环戊烯化合物
CN1476434A (zh)	2004-02-18	新化合物
CN1150419A (zh)	1997-05-21	新的法呢基转移酶抑制剂、其制法及其药物组合物
CN87108160A (zh)	1988-09-14	制备和应用具有活性羰基的唾液酸衍生物的方法
CN1055537A (zh)	1991-10-23	3，5-双取代-2-异唑烷和异唑、其制备方法，含有该成分的制剂及其应用
CN1918160A (zh)	2007-02-21	用作趋化因子受体活性调节剂的新颖三环螺环衍生物
CN1062536A (zh)	1992-07-08	从3-氯-2-氯甲基-1-丙烯衍生的逆转录酶病毒蛋白酶抑制剂
CN1398964A (zh)	2003-02-26	制备l－精氨酸的方法
CN1031267C (zh)	1996-03-13	具有抗痴功效的血管紧张素转化酶抑制剂的制备方法
CN1033633A (zh)	1989-07-05	新型同多肽及其制备方法
CN1215052C (zh)	2005-08-17	异羟肟酸的磺酸衍生物及其医药用途
CN1049166A (zh)	1991-02-13	Magainin肽的取代类似物
CN1899610A (zh)	2007-01-24	幽门螺杆菌抗原重组疫苗
CN87102538A (zh)	1987-11-18	与斯柏葛埃林有关的新化合物及其制备方法
CN85101425A (zh)	1987-01-17	带有次苯基的斯伯格埃林有关化合物及其制备方法
CN1079744A (zh)	1993-12-22	7-氧代-7H-吡啶并[1，2，3，-d，e][1，4]苯并嗪-6-羧酸及其酯
CN1148378C (zh)	2004-05-05	15-脱氧精胍林类似物、其制备方法及其治疗应用
CN1025617C (zh)	1994-08-10	制备嘧啶衍生物及其医药上可用的盐的方法
CN1827640A (zh)	2006-09-06	血管生成抑制多肽及其制备方法和应用

CN1033633A - 新型同多肽及其制备方法 - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=10968769

Family Applications (1)

Country Status (13)

Cited By (1)

Families Citing this family (5)

Cited By (1)

Also Published As

Similar Documents

Legal Events