LU87633A1 - Derives peptidiques - Google Patents

Derives peptidiques Download PDF

Info

Publication number: LU87633A1
Authority: LU; Luxembourg
Prior art keywords: group; peptide; somatostatin; chelating; free form
Prior art date: 1988-12-05

Application number

LU87633A

Other languages

English (en)

French (fr)

Original Assignee

Sandoz Sa

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.)

1988-12-05

Filing date

1989-12-05

Publication date

1991-09-18

1988-12-05 Priority claimed from GB888828364A external-priority patent/GB8828364D0/en

1989-07-13 Priority claimed from GB898916115A external-priority patent/GB8916115D0/en

1989-07-21 Priority claimed from GB898916761A external-priority patent/GB8916761D0/en

1989-12-05 Application filed by Sandoz Sa filed Critical Sandoz Sa

1991-09-18 Publication of LU87633A1 publication Critical patent/LU87633A1/fr

Links

108090000765 processed proteins & peptides Proteins 0.000 title claims description 42
108010056088 Somatostatin Proteins 0.000 claims description 62
150000003839 salts Chemical class 0.000 claims description 44
229910052739 hydrogen Inorganic materials 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 40
239000013522 chelant Substances 0.000 claims description 37
238000000034 method Methods 0.000 claims description 28
206010028980 Neoplasm Diseases 0.000 claims description 26
125000003277 amino group Chemical group 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
108050001286 Somatostatin Receptor Proteins 0.000 claims description 18
102000011096 Somatostatin receptor Human genes 0.000 claims description 18
239000002738 chelating agent Substances 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
-1 oxime derivatives of propyleneamine Chemical class 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 claims description 12
229960003330 pentetic acid Drugs 0.000 claims description 12
150000003254 radicals Chemical class 0.000 claims description 12
125000006850 spacer group Chemical group 0.000 claims description 12
102000007079 Peptide Fragments Human genes 0.000 claims description 11
108010033276 Peptide Fragments Proteins 0.000 claims description 11
230000008569 process Effects 0.000 claims description 11
206010027476 Metastases Diseases 0.000 claims description 10
150000001413 amino acids Chemical group 0.000 claims description 10
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 9
235000001014 amino acid Nutrition 0.000 claims description 9
125000000524 functional group Chemical group 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
238000003384 imaging method Methods 0.000 claims description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
108010016626 Dipeptides Proteins 0.000 claims description 6
150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 6
235000008206 alpha-amino acids Nutrition 0.000 claims description 6
125000000539 amino acid group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 5
230000008030 elimination Effects 0.000 claims description 5
238000003379 elimination reaction Methods 0.000 claims description 5
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239000012216 imaging agent Substances 0.000 claims description 5
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125000003884 phenylalkyl group Chemical group 0.000 claims description 5
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125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 claims description 4
229930182832 D-phenylalanine Natural products 0.000 claims description 4
125000003877 L-cysteinyl radical group Chemical group 0.000 claims description 4
229910003204 NH2 Inorganic materials 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
WDLRUFUQRNWCPK-UHFFFAOYSA-N Tetraxetan Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 WDLRUFUQRNWCPK-UHFFFAOYSA-N 0.000 claims description 3
125000003275 alpha amino acid group Chemical group 0.000 claims description 3
150000001414 amino alcohols Chemical class 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
UWPXWOJLMYFRGY-VKHMYHEASA-N (2s)-2-(difluoroamino)-2,3,3-trifluoropropanoic acid Chemical compound OC(=O)[C@](F)(C(F)F)N(F)F UWPXWOJLMYFRGY-VKHMYHEASA-N 0.000 claims description 2
DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 claims description 2
NKIJBSVPDYIEAT-UHFFFAOYSA-N 1,4,7,10-tetrazacyclododec-10-ene Chemical class C1CNCCN=CCNCCN1 NKIJBSVPDYIEAT-UHFFFAOYSA-N 0.000 claims description 2
MDAXKAUIABOHTD-UHFFFAOYSA-N 1,4,8,11-tetraazacyclotetradecane Chemical compound C1CNCCNCCCNCCNC1 MDAXKAUIABOHTD-UHFFFAOYSA-N 0.000 claims description 2
GRUVVLWKPGIYEG-UHFFFAOYSA-N 2-[2-[carboxymethyl-[(2-hydroxyphenyl)methyl]amino]ethyl-[(2-hydroxyphenyl)methyl]amino]acetic acid Chemical compound C=1C=CC=C(O)C=1CN(CC(=O)O)CCN(CC(O)=O)CC1=CC=CC=C1O GRUVVLWKPGIYEG-UHFFFAOYSA-N 0.000 claims description 2
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
150000008574 D-amino acids Chemical class 0.000 claims description 2
108010016076 Octreotide Proteins 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
150000001576 beta-amino acids Chemical class 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
125000006289 hydroxybenzyl group Chemical group 0.000 claims description 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
229910052738 indium Inorganic materials 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
229960002700 octreotide Drugs 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
150000004032 porphyrins Chemical class 0.000 claims description 2
239000012217 radiopharmaceutical Substances 0.000 claims description 2
229940121896 radiopharmaceutical Drugs 0.000 claims description 2
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125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 7
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims 3
239000003937 drug carrier Substances 0.000 claims 3
239000008024 pharmaceutical diluent Substances 0.000 claims 3
239000003795 chemical substances by application Substances 0.000 claims 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
239000005977 Ethylene Substances 0.000 claims 1
HPECNYCQLSVCHH-BZSNNMDCSA-N Phe-Cys-Phe Chemical compound C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O)N HPECNYCQLSVCHH-BZSNNMDCSA-N 0.000 claims 1
QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical group CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
238000001959 radiotherapy Methods 0.000 claims 1
238000011084 recovery Methods 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
229940124597 therapeutic agent Drugs 0.000 claims 1
239000003446 ligand Substances 0.000 description 35
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
229910021645 metal ion Inorganic materials 0.000 description 13
NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 13
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238000001727 in vivo Methods 0.000 description 11
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
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150000007513 acids Chemical class 0.000 description 4
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239000007858 starting material Substances 0.000 description 4
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QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
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GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical compound [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 description 1
ISWQCIVKKSOKNN-UHFFFAOYSA-L Tiron Chemical compound [Na+].[Na+].OC1=CC(S([O-])(=O)=O)=CC(S([O-])(=O)=O)=C1O ISWQCIVKKSOKNN-UHFFFAOYSA-L 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
241000221012 Viscum Species 0.000 description 1
229910052769 Ytterbium Inorganic materials 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
RUSUZAGBORAKPY-UHFFFAOYSA-N acetic acid;n'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.NCCNCCNCCN RUSUZAGBORAKPY-UHFFFAOYSA-N 0.000 description 1
125000004450 alkenylene group Chemical group 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229960002684 aminocaproic acid Drugs 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229960003071 bacitracin Drugs 0.000 description 1
229930184125 bacitracin Natural products 0.000 description 1
CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 description 1
229940098773 bovine serum albumin Drugs 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
208000029742 colonic neoplasm Diseases 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
238000002591 computed tomography Methods 0.000 description 1
238000011109 contamination Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000011033 desalting Methods 0.000 description 1
238000002405 diagnostic procedure Methods 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
210000005095 gastrointestinal system Anatomy 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
238000011534 incubation Methods 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
208000020816 lung neoplasm Diseases 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
201000000050 myeloid neoplasm Diseases 0.000 description 1
239000013110 organic ligand Substances 0.000 description 1
230000002611 ovarian Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
201000002528 pancreatic cancer Diseases 0.000 description 1
208000007312 paraganglioma Diseases 0.000 description 1
210000003899 penis Anatomy 0.000 description 1
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
208000028591 pheochromocytoma Diseases 0.000 description 1
230000001817 pituitary effect Effects 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
238000002600 positron emission tomography Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
208000023958 prostate neoplasm Diseases 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000000163 radioactive labelling Methods 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000002791 soaking Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
229910052713 technetium Inorganic materials 0.000 description 1
229940056501 technetium 99m Drugs 0.000 description 1
GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
238000003325 tomography Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
210000003708 urethra Anatomy 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
238000012800 visualization Methods 0.000 description 1
NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
JPZXHKDZASGCLU-LBPRGKRZSA-N β-(2-naphthyl)-alanine Chemical compound C1=CC=CC2=CC(C[C@H](N)C(O)=O)=CC=C21 JPZXHKDZASGCLU-LBPRGKRZSA-N 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
- 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
- C07K14/575—Hormones
- C07K14/655—Somatostatins
- C07K14/6555—Somatostatins at least 1 amino acid in D-form
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
- 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)
Biochemistry (AREA)
Endocrinology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Molecular Biology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Bioinformatics & Cheminformatics (AREA)
Gastroenterology & Hepatology (AREA)
Zoology (AREA)
Toxicology (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Peptides Or Proteins (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

LU87633A 1988-12-05 1989-12-05 Derives peptidiques LU87633A1 (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
GB8828364		1988-12-05
GB888828364A GB8828364D0 (en)	1988-12-05	1988-12-05	Improvements in/relating to organic compounds
GB898916115A GB8916115D0 (en)	1989-07-13	1989-07-13	Improvements in or relating to organic compounds
GB8916115		1989-07-13
GB8916761		1989-07-21
GB898916761A GB8916761D0 (en)	1989-07-21	1989-07-21	Improvements in or relating to organic compounds

Publications (1)

Publication Number	Publication Date
LU87633A1 true LU87633A1 (fr)	1991-09-18

Family

ID=27264222

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87633A LU87633A1 (fr)	1988-12-05	1989-12-05	Derives peptidiques

Country Status (24)

Country	Link
JP (2)	JP2726320B2 (de)
KR (1)	KR0156541B1 (de)
AT (1)	AT403476B (de)
AU (1)	AU633859B2 (de)
BE (1)	BE1002296A5 (de)
CA (1)	CA2004532C (de)
CH (1)	CH678329A5 (de)
DE (1)	DE3991505B4 (de)
DK (1)	DK175338B1 (de)
ES (1)	ES2023533A6 (de)
FI (1)	FI102540B1 (de)
FR (1)	FR2639947B1 (de)
GB (1)	GB2225579B (de)
HK (1)	HK189995A (de)
HU (2)	HUT53375A (de)
IE (1)	IE62091B1 (de)
IL (1)	IL92534A (de)
LU (1)	LU87633A1 (de)
MY (1)	MY106120A (de)
NL (1)	NL194828C (de)
PT (1)	PT92487B (de)
SA (1)	SA96160495B1 (de)
SE (1)	SE508799C2 (de)
WO (1)	WO1990006949A2 (de)

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AU639371B2 (en) *	1987-07-10	1993-07-22	Novartis Ag	Method of treating breast cancer
DE3822557C2 (de) *	1987-07-10	1998-07-02	Ciba Geigy Ag	Arzneimittel, enthaltend Somatostatine
GB9111199D0 (en) *	1991-05-23	1991-07-17	Sandoz Ltd	Improvements in or relating to organic compounds
US5460785A (en) *	1989-08-09	1995-10-24	Rhomed Incorporated	Direct labeling of antibodies and other protein with metal ions
US5700444A (en) *	1992-02-20	1997-12-23	Rhomed Incorporated	Chemotactic peptide pharmaceutical applications
US5985240A (en) *	1989-08-09	1999-11-16	Rhomed Incorporated	Peptide radiopharmaceutical applications
US5443816A (en) *	1990-08-08	1995-08-22	Rhomed Incorporated	Peptide-metal ion pharmaceutical preparation and method
GB9004017D0 (en) *	1990-02-22	1990-04-18	Krenning Eric P	Improvements in or relating to organic compounds
US5382654A (en) *	1992-02-05	1995-01-17	Mallinckrodt Medical, Inc.	Radiolabelled peptide compounds
US5849261A (en) *	1991-02-08	1998-12-15	Diatide, Inc.	Radiolabeled vasoactive intestinal peptides for diagnosis and therapy
US7238340B1 (en)	1991-11-27	2007-07-03	Cis Bio International	Monoamine, diamide, thiol-containing metal chelating agents
US5443815A (en) *	1991-11-27	1995-08-22	Diatech, Inc.	Technetium-99m labeled peptides for imaging
IE920416A1 (en) *	1991-02-08	1992-08-12	Biomeasure	Method of treating benign and malignant proliferative skin¹disease
AU657770B2 (en) *	1991-06-03	1995-03-23	Mallinckrodt Medical, Inc.	Radiolabelled somatostatin derivatives, their preparation and use
WO1993004702A1 (en) *	1991-08-29	1993-03-18	Mallinckrodt Medical, Inc.	Use of gentisic acid or gentisyl alcohol for stabilising radiolabeled peptides and proteins
US5225180A (en) *	1991-09-10	1993-07-06	Diatech, Inc.	Technetium-99m labeled somatostatin-derived peptides for imaging
US5783170A (en) *	1991-11-27	1998-07-21	Diatide, Inc.	Peptide-metal chelate conjugates
AU683833B2 (en) *	1992-01-03	1997-11-27	Rhomed Incorporated	Protein- and peptide-metal ion pharmaceutical applications
US5738838A (en) *	1992-02-20	1998-04-14	Rhomed Incorporated	IKVAV peptide radiopharmaceutical applications
US5556609A (en) *	1992-02-20	1996-09-17	Rhomed Incorporated	YIGSR peptide radiopharmaceutical applications
EP0642357B1 (de) *	1992-02-05	2001-07-25	Mallinckrodt Inc.	Radioaktiv markierte somatostatin
US5371184A (en) *	1992-02-05	1994-12-06	Mallinckrodt Medical, Inc.	Radiolabelled peptide compounds
US5643549A (en) *	1992-02-20	1997-07-01	Rhomed Incorporated	Leukostimulatory agent for in vivo leukocyte tagging
EP0636032A1 (de) *	1992-03-25	1995-02-01	Mallinckrodt Medical, Inc.	Methode zur Feststellung und Lokalisierung von Tumorgeweben während einerOperation
US6017512A (en) *	1992-06-23	2000-01-25	Diatide, Inc.	Radiolabeled peptides
US5871711A (en) *	1992-06-23	1999-02-16	Diatide, Inc.	Radioactively-labeled somatostatin-derived peptides for imaging and therapeutic uses
US5620675A (en) *	1992-06-23	1997-04-15	Diatech, Inc.	Radioactive peptides
US5716596A (en) *	1992-06-23	1998-02-10	Diatide, Inc.	Radioactively labeled somatostatin-derived peptides for imaging and therapeutic uses
US5650134A (en) *	1993-01-12	1997-07-22	Novartis Ag (Formerly Sandoz Ltd.)	Peptides
FI940109A7 (fi) *	1993-01-12	1994-10-11	Novartis Ag	Peptidejä
CA2154667A1 (en) *	1993-02-02	1994-08-18	Linda M. Gustavson	Directed biodistribution of small molecules
US5879657A (en) *	1993-03-30	1999-03-09	The Dupont Merck Pharmaceutical Company	Radiolabeled platelet GPIIb/IIIa receptor antagonists as imaging agents for the diagnosis of thromboembolic disorders
US5932189A (en) *	1994-07-29	1999-08-03	Diatech, Inc.	Cyclic peptide somatostatin analogs
EP0720621B1 (de) *	1993-06-23	2001-02-07	Diatide, Inc.	Radiomarkierte somatostatin derivate zur abbildung und zur therapeutischen verwendung
CA2190727C (en) *	1994-05-19	2006-07-18	Sudhakar Kasina	Aromatic amine substituted bridged nitrogen and sulfur donor atom ligands for imaging
US6051206A (en) *	1994-06-03	2000-04-18	Diatide, Inc	Radiolabeled somatostatin-derived peptides for imaging and therapeutic uses
GB9417873D0 (en) *	1994-09-06	1994-10-26	Sandoz Ltd	Organic compounds
US5632969A (en) *	1994-10-13	1997-05-27	Merck & Co., Inc.	N3 S2 chelating ligands optionally radiolabelled with Tc or Re, useful for diagnostic or therapeutic applications
US5556939A (en) *	1994-10-13	1996-09-17	Merck Frosst Canada, Inc.	TC or RE radionuclide labelled chelate, hexapeptide complexes useful for diagnostic or therapeutic applications
US5830431A (en) *	1995-06-07	1998-11-03	Mallinckrodt Medical, Inc.	Radiolabeled peptide compositions for site-specific targeting
GB9708265D0 (en)	1997-04-24	1997-06-18	Nycomed Imaging As	Contrast agents
FI965181L (fi) *	1996-12-20	1998-06-21	Map Medical Technologies Oy	Polyalkoholi-peptidijohdannaiset
US6630570B1 (en)	1999-04-09	2003-10-07	Insitut für Diagnostikforschung GmbH	Short-chain peptide-dye conjugates as contrast media for optical diagnosis
DE19917713A1 (de) *	1999-04-09	2000-10-19	Diagnostikforschung Inst	Kurzkettige Peptid-Farbstoffkonjugate als Konstrastmittel für die optische Diagnostik
US7175953B2 (en)	1999-04-09	2007-02-13	Institute Fuer Diagnostik Forschung	Short-warp peptide-dye conjugate as contrast agent for optical diagnostic
US6685914B1 (en)	1999-09-13	2004-02-03	Bristol-Myers Squibb Pharma Company	Macrocyclic chelants for metallopharmaceuticals
ATE427125T1 (de)	2001-04-23	2009-04-15	Mallinckrodt Inc	Tc und re markierte radioaktive glycosylierte octreotid-derivate
US7968080B2 (en)	2003-08-20	2011-06-28	The Regents Of The University Of California	Somatostatin analogs with inhibitory activity to growth hormone release
US7611693B2 (en) *	2003-09-17	2009-11-03	Board Of Regents, The Univerisity Of Texas System	Mechanism-based targeted pancreatic beta cell imaging and therapy
EP2067786A1 (de)	2007-12-07	2009-06-10	ITALFARMACO S.p.A.	Neue nichtselektive Analoga von Somatostatin
EP2922578B1 (de)	2012-11-21	2018-12-12	Serene, Llc	Tin-117m-somatostatinrezeptor-bindende verbindungen
CN119708199A (zh)	2023-09-27	2025-03-28	钱杭江医药科技(嘉兴)有限公司	生长抑素肽类类似物、螯合物及其应用

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CA1222691A (en) *	1981-12-29	1987-06-09	Wilhelmus T. Goedemans	Method of preparing radionuclide-labelled proteins, in particular antibodies or antibody fragments
US4652519A (en) *	1983-02-03	1987-03-24	Yeda Research And Development Company Limited	Bifunctional chelating agents and process for their production
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DE3511206A1 (de) *	1985-03-28	1986-10-09	Sandoz-Patent-GmbH, 7850 Lörrach	Neue polypeptidderivate, ihre herstellung und pharmazeutische praeparate, welche diese polypeptidderivate enthalten
HUT42101A (en) *	1985-01-07	1987-06-29	Sandoz Ag	Process for preparing stomatostatine derivatives and pharmaceutical compositions containing such compounds
DE3522638A1 (de) *	1985-06-25	1987-01-08	Diamalt Ag	Neue somatostatin-derivate
US4678667A (en) *	1985-07-02	1987-07-07	501 Regents of the University of California	Macrocyclic bifunctional chelating agents
CA1266344A (en) *	1986-02-14	1990-02-27	Miki Kurami	High molecular compounds having amino groups, and their utilization
US4732974A (en) *	1986-03-05	1988-03-22	Mallinckrodt, Inc.	Metal ion labeling of carrier molecules
US4861869A (en) *	1986-05-29	1989-08-29	Mallinckrodt, Inc.	Coupling agents for joining radionuclide metal ions with biologically useful proteins
HU906340D0 (en) *	1986-10-13	1991-04-29	Sandoz Ag	Synthesis in solid phase for producing peptonic alcohols
CH679045A5 (de) *	1987-06-29	1991-12-13	Sandoz Ag
US5073541A (en) *	1987-11-18	1991-12-17	Administrators Of The Tulane Educational Fund	Treatment of small cell lung cancer with somatostatin analogs
FR2638968B1 (fr) *	1988-11-11	1994-10-07	Sandoz Sa	Nouvelle utilisation therapeutique de la somatostatine et de ses analogues et derives

1989
- 1989-11-29 MY MYPI89001655A patent/MY106120A/en unknown
- 1989-11-30 WO PCT/EP1989/001448 patent/WO1990006949A2/en not_active Ceased
- 1989-11-30 CH CH2578/90A patent/CH678329A5/de not_active IP Right Cessation
- 1989-11-30 AT AT0901789A patent/AT403476B/de active
- 1989-11-30 DE DE3991505A patent/DE3991505B4/de not_active Expired - Lifetime
- 1989-12-01 GB GB8927255A patent/GB2225579B/en not_active Expired - Lifetime
- 1989-12-04 KR KR1019890018033A patent/KR0156541B1/ko not_active Expired - Lifetime
- 1989-12-04 NL NL8902981A patent/NL194828C/nl not_active IP Right Cessation
- 1989-12-04 JP JP1315124A patent/JP2726320B2/ja not_active Expired - Lifetime
- 1989-12-04 HU HU896359A patent/HUT53375A/hu unknown
- 1989-12-04 IE IE386689A patent/IE62091B1/en not_active IP Right Cessation
- 1989-12-04 SE SE8904087A patent/SE508799C2/sv unknown
- 1989-12-04 AU AU45871/89A patent/AU633859B2/en not_active Expired
- 1989-12-04 FI FI895809A patent/FI102540B1/fi active IP Right Grant
- 1989-12-04 CA CA002004532A patent/CA2004532C/en not_active Expired - Lifetime
- 1989-12-04 FR FR8915993A patent/FR2639947B1/fr not_active Expired - Lifetime
- 1989-12-04 PT PT92487A patent/PT92487B/pt active IP Right Grant
- 1989-12-04 IL IL9253489A patent/IL92534A/en not_active IP Right Cessation
- 1989-12-05 ES ES8904151A patent/ES2023533A6/es not_active Expired - Lifetime
- 1989-12-05 LU LU87633A patent/LU87633A1/fr unknown
- 1989-12-05 DK DK198906126A patent/DK175338B1/da not_active IP Right Cessation
- 1989-12-05 BE BE8901294A patent/BE1002296A5/fr not_active IP Right Cessation
1995
- 1995-06-15 HU HU95P/P00214P patent/HU211468A9/hu unknown
- 1995-12-21 HK HK189995A patent/HK189995A/xx not_active IP Right Cessation
1996
- 1996-01-01 SA SA96160495A patent/SA96160495B1/ar unknown
1997
- 1997-08-04 JP JP20891597A patent/JP3686503B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NL194828B (nl)	2002-12-02
GB2225579B (en)	1993-03-17
FR2639947A1 (fr)	1990-06-08
IE62091B1 (en)	1994-12-14
CH678329A5 (de)	1991-08-30
FI102540B (fi)	1998-12-31
AU633859B2 (en)	1993-02-11
KR0156541B1 (ko)	1998-10-15
SA96160495B1 (ar)	2006-08-23
WO1990006949A3 (en)	1990-07-26
CA2004532C (en)	2000-02-22
ATA901789A (de)	1997-07-15
JPH1095737A (ja)	1998-04-14
PT92487B (pt)	1996-01-31
AU4587189A (en)	1990-06-14
DK612689A (da)	1990-06-06
HU896359D0 (en)	1990-02-28
JP2726320B2 (ja)	1998-03-11
HU211468A9 (en)	1995-11-28
FI895809A0 (fi)	1989-12-04
DE3991505B4 (de)	2006-04-20
GB8927255D0 (en)	1990-01-31
AT403476B (de)	1998-02-25
JPH02184698A (ja)	1990-07-19
SE8904087D0 (sv)	1989-12-04
JP3686503B2 (ja)	2005-08-24
FI102540B1 (fi)	1998-12-31
NL194828C (nl)	2003-04-03
HK189995A (en)	1995-12-29
GB2225579A (en)	1990-06-06
FR2639947B1 (fr)	1995-04-21
KR900009697A (ko)	1990-07-05
ES2023533A6 (es)	1992-01-16
WO1990006949A2 (en)	1990-06-28
HUT53375A (en)	1990-10-28
IE893866L (en)	1990-06-05
PT92487A (pt)	1990-06-29
IL92534A (en)	1994-06-24
CA2004532A1 (en)	1990-06-05
DK175338B1 (da)	2004-08-30
MY106120A (en)	1995-03-31
BE1002296A5 (fr)	1990-11-20
SE508799C2 (sv)	1998-11-09
SE8904087L (sv)	1991-06-05
NL8902981A (nl)	1990-07-02
DK612689D0 (da)	1989-12-05

Publication	Publication Date	Title
LU87633A1 (fr)	1991-09-18	Derives peptidiques
EP2790732B1 (de)	2016-03-09	Geklickte, somatostatinkonjugierte analoga für biologische anwendungen
EP1872800B1 (de)	2012-10-17	Radioaktiv markierte Peptid beinhaltende zusammensetzungen für ortspezifisches Targeting
US5776894A (en)	1998-07-07	Chelated somatostatin peptides and complexes thereof, pharmaceutical compositions containing them and their use in treating tumors
US5753627A (en)	1998-05-19	Use of certain complexed somatostatin peptides for the invivo imaging of somatostatin receptor-positive tumors and metastasis
JP2005508886A (ja)	2005-04-07	ソマトスタチン類似体とそれらの使用、全てのソマトスタチンレセプターと結合するソマトスタチン類似体およびそれらの使用
BE1004645A3 (fr)	1993-01-05	Nouvelle utilisation therapeutique de peptides derives de la somatostatine.
JP6410339B2 (ja)	2018-10-24	放射性核種標識オクトレオチド誘導体
EP0741747A1 (de)	1996-11-13	Serinproteasen-inhibitoren mit chelatbildender gruppe
EP0498771A2 (de)	1992-08-12	MSH Peptidderivate
FI101967B (fi)	1998-09-30	Menetelmä farmaseuttisesti käyttökelpoisen radionuklidin kanssa komple ksoidun ligandin valmistamiseksi
FR2697255A1 (fr)	1994-04-29	Nouveaux dérivés bihaptènes liant le technétium, application au diagnostic et à la thérapeutique, kits et réactifs immunologiques les mettant en Óoeuvre.
EP0115227B1 (de)	1987-03-18	Peptidische Verbindungen, Verfahren zu deren Herstellung und deren pharmazeutische Verwendung
TW202540073A (zh)	2025-10-16	靶向ｓｓｔｒ受體的放射性化合物及其用途
CY1893A (en)	1996-08-30	Detectable somatostatin analogues containing a chelating group
FR2629824A1 (fr)	1989-10-13	Nouveaux peptides de la somatostatine, leur preparation et leur utilisation comme medicaments