CA1079268A - Substances immunologiques - Google Patents

Substances immunologiques

Info

Publication number: CA1079268A
Authority: CA; Canada
Prior art keywords: amino; bis; chloroethyl; polymer carrier; phenyl
Prior art date: 1975-02-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA314,487A

Other languages

English (en)

Inventor

George F. Rowland

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.)

GD Searle and Co Ltd

Original Assignee

GD Searle and Co Ltd

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.)

1975-02-04

Filing date

1978-10-27

Publication date

1980-06-10

1975-02-04 Priority claimed from GB4695/75A external-priority patent/GB1496011A/en

1976-02-04 Priority claimed from CA245,033A external-priority patent/CA1062156A/fr

1978-10-27 Application filed by GD Searle and Co Ltd filed Critical GD Searle and Co Ltd

1978-10-27 Priority to CA314,487A priority Critical patent/CA1079268A/fr

1980-06-10 Application granted granted Critical

1980-06-10 Publication of CA1079268A publication Critical patent/CA1079268A/fr

Status Expired legal-status Critical Current

Links

239000000463 material Substances 0.000 title description 8
230000001900 immune effect Effects 0.000 title description 2
229920000642 polymer Polymers 0.000 claims abstract description 79
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 69
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 32
229940127089 cytotoxic agent Drugs 0.000 claims abstract description 32
239000002254 cytotoxic agent Substances 0.000 claims abstract description 32
108060003951 Immunoglobulin Proteins 0.000 claims abstract description 28
102000018358 immunoglobulin Human genes 0.000 claims abstract description 28
FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 claims description 45
238000000034 method Methods 0.000 claims description 34
229920002307 Dextran Polymers 0.000 claims description 33
125000003277 amino group Chemical group 0.000 claims description 29
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 26
238000002360 preparation method Methods 0.000 claims description 26
229920002643 polyglutamic acid Polymers 0.000 claims description 22
108090000765 processed proteins & peptides Proteins 0.000 claims description 20
108010020346 Polyglutamic Acid Proteins 0.000 claims description 19
150000004986 phenylenediamines Chemical class 0.000 claims description 19
229920000656 polylysine Polymers 0.000 claims description 16
-1 2,4-diamino-6-pteridinyl Chemical group 0.000 claims description 15
229920002873 Polyethylenimine Polymers 0.000 claims description 15
108010039918 Polylysine Proteins 0.000 claims description 15
229960005190 phenylalanine Drugs 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 13
229960002989 glutamic acid Drugs 0.000 claims description 13
SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 12
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims description 10
JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 10
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 9
150000001718 carbodiimides Chemical class 0.000 claims description 9
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 9
235000008729 phenylalanine Nutrition 0.000 claims description 9
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AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
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125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 8
229940080818 propionamide Drugs 0.000 claims description 8
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 6
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 claims description 4
WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 claims description 4
229920001577 copolymer Polymers 0.000 claims description 4
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 claims description 4
229960004679 doxorubicin Drugs 0.000 claims description 4
229920000724 poly(L-arginine) polymer Polymers 0.000 claims description 4
108010011110 polyarginine Proteins 0.000 claims description 4
KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 claims description 3
102000016607 Diphtheria Toxin Human genes 0.000 claims description 3
108010053187 Diphtheria Toxin Proteins 0.000 claims description 3
102000008946 Fibrinogen Human genes 0.000 claims description 3
108010049003 Fibrinogen Proteins 0.000 claims description 3
229920000805 Polyaspartic acid Polymers 0.000 claims description 3
229940012952 fibrinogen Drugs 0.000 claims description 3
108010064470 polyaspartate Proteins 0.000 claims description 3
IERHLVCPSMICTF-UHFFFAOYSA-N Cytosine arabinoside monophosphate Chemical compound O=C1N=C(N)C=CN1C1C(O)C(O)C(COP(O)(O)=O)O1 IERHLVCPSMICTF-UHFFFAOYSA-N 0.000 claims 2
KVLZELYWWJRKHH-JTQLQIEISA-N (2s)-2-[4-[bis(2-chloroethyl)amino]anilino]propanoic acid Chemical compound OC(=O)[C@H](C)NC1=CC=C(N(CCCl)CCCl)C=C1 KVLZELYWWJRKHH-JTQLQIEISA-N 0.000 claims 1
TXFLGZOGNOOEFZ-UHFFFAOYSA-N bis(2-chloroethyl)amine Chemical compound ClCCNCCCl TXFLGZOGNOOEFZ-UHFFFAOYSA-N 0.000 claims 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
239000000243 solution Substances 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
210000004027 cell Anatomy 0.000 description 22
229960002086 dextran Drugs 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
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239000003814 drug Substances 0.000 description 19
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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239000011780 sodium chloride Substances 0.000 description 14
238000007792 addition Methods 0.000 description 13
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 11
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241000283707 Capra Species 0.000 description 9
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239000002244 precipitate Substances 0.000 description 7
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
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DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000000969 carrier Substances 0.000 description 6
229940072221 immunoglobulins Drugs 0.000 description 6
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208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
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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
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UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
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239000008272 agar Substances 0.000 description 1
ZRPDXDBGEYHEBJ-UHFFFAOYSA-N alpha-(hydroxymethyl)serine Chemical compound OCC(N)(CO)C(O)=O ZRPDXDBGEYHEBJ-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
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235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
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239000012491 analyte Substances 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
210000000628 antibody-producing cell Anatomy 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-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
230000004071 biological effect Effects 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical group ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
239000001045 blue dye Substances 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
230000004540 complement-dependent cytotoxicity Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
239000012043 crude product Substances 0.000 description 1
229940104302 cytosine Drugs 0.000 description 1
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
229910000071 diazene Inorganic materials 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 1
229960000961 floxuridine Drugs 0.000 description 1
239000010200 folin Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
229940106780 human fibrinogen Drugs 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000028709 inflammatory response Effects 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
208000003747 lymphoid leukemia Diseases 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229960001924 melphalan Drugs 0.000 description 1
230000001613 neoplastic effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229920001308 poly(aminoacid) Polymers 0.000 description 1
229920001184 polypeptide Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000010791 quenching Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
PIEPQKCYPFFYMG-UHFFFAOYSA-N tris acetate Chemical compound CC(O)=O.OCC(N)(CO)CO PIEPQKCYPFFYMG-UHFFFAOYSA-N 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
239000010457 zeolite Substances 0.000 description 1

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CA314,487A 1975-02-04 1978-10-27 Substances immunologiques Expired CA1079268A (fr)

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Application Number	Priority Date	Filing Date	Title
CA314,487A CA1079268A (fr)	1975-02-04	1978-10-27	Substances immunologiques

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Application Number	Priority Date	Filing Date	Title
GB4695/75A GB1496011A (en)	1974-11-22	1975-02-04	Defoaming composition
CA245,033A CA1062156A (fr)	1975-02-04	1976-02-04	Produits immunologiques
CA314,487A CA1079268A (fr)	1975-02-04	1978-10-27	Substances immunologiques

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CA1079268A true CA1079268A (fr)	1980-06-10

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CA314,487A Expired CA1079268A (fr)	1975-02-04	1978-10-27	Substances immunologiques

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5057313A (en) *	1986-02-25	1991-10-15	The Center For Molecular Medicine And Immunology	Diagnostic and therapeutic antibody conjugates
US5084560A (en) *	1986-06-30	1992-01-28	Oncogen	Immunoconjugates and methods for their use in tumor therapy
US5162505A (en) *	1989-09-19	1992-11-10	Centocor	Proteins modified with positively charged carriers and compositions prepared therefrom

1978
- 1978-10-27 CA CA314,487A patent/CA1079268A/fr not_active Expired

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5057313A (en) *	1986-02-25	1991-10-15	The Center For Molecular Medicine And Immunology	Diagnostic and therapeutic antibody conjugates
US5084560A (en) *	1986-06-30	1992-01-28	Oncogen	Immunoconjugates and methods for their use in tumor therapy
US5162505A (en) *	1989-09-19	1992-11-10	Centocor	Proteins modified with positively charged carriers and compositions prepared therefrom

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Date	Code	Title	Description
1997-06-10	MKEX	Expiry

Publication	Publication Date	Title
CA1062156A (fr)	1979-09-11	Produits immunologiques
US5140104A (en)	1992-08-18	Amine derivatives of folic acid analogs
AU610062B2 (en)	1991-05-16	Diagnostic and therapeutic antibody conjugates
US5057313A (en)	1991-10-15	Diagnostic and therapeutic antibody conjugates
KR101711903B1 (ko)	2017-03-03	복합 다가 면역원성 콘쥬게이트의 제조 방법
JP2564586B2 (ja)	1996-12-18	葉酸類縁体のアミン誘導体
Alkan et al.	1971	Antigen recognition and the immune response: the capacity of L-tyrosine-azobenzenearsonate to serve as a carrier for a macromolecular hapten
CA2128330A1 (fr)	1993-07-22	Systeme de liberation simultanee de medicaments activables par des enzymes en presence de lumiere
JPS5843926A (ja)	1983-03-14	選択性制癌剤
AU619614B2 (en)	1992-01-30	Antibody-drug conjugates
Tsukada et al.	1984	An anti-α-fetoprotein antibody-daunorubicin conjugate with a novel poly-L-glutamic acid derivative as intermediate drug carrier
JP3273608B2 (ja)	2002-04-08	治療薬の部位特異的インビボ活性化
EP0325270A2 (fr)	1989-07-26	Conjuges anticancereux
Umemoto et al.	1989	Preparation and in vitro cytotoxicity of a methotrexate‐anti‐MM46 monoclonal antibody conjugate via an oligopeptide spacer
CA1079268A (fr)	1980-06-10	Substances immunologiques
US5672688A (en)	1997-09-30	Immunoglobulin Fc fragment bound to an alkylating, antibiotic, or antimetabolic antitum or substance
Kato et al.	1984	A novel method of conjugation of daunomycin with antibody with a poly (L-glutamic acid) derivative as intermediate drug carrier. An anti-. alpha.-fetoprotein antibody-daunomycin conjugate
JP2736255B2 (ja)	1998-04-02	イムノグロブリン結合体
JPS62167800A (ja)	1987-07-24	オシド単位の酸化およびシツフ塩基の形成により変性されたリボソ−ム不活性化糖タンパク、およびこの糖タンパクを含む生体内持続性免疫毒素
EP0485749A2 (fr)	1992-05-20	Modification chimique d'anticorps pour la création d'immunoconjugués
JPH08509698A (ja)	1996-10-15	蛋白質複合体、それを含む組成物及びその医薬としての用途
Schneider et al.	1979	Monovalent elicitation of passive cutaneous anaphylaxis by N1-DNCP-N6-BPO-diaminohexane
Hoes et al.	1993	Design of soluble conjugates of biodegradable polymeric carriers and adriamycin
CA2121990A1 (fr)	1994-10-29	Conjugues anticorps-medicament
EP0489220A1 (fr)	1992-06-10	Dérivés N,N-bis(succinyl-peptidiques) cytotoxiques d'1,4-bis(aminoalkyl)-5,8-dihydroxyanthraquinones et leurs conjuqués d'anticorps

CA1079268A - Substances immunologiques - Google Patents

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Applications Claiming Priority (3)

Publications (1)

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ID=27164318

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Cited By (3)

Cited By (3)

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