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US 6,441,131 B1Granted
Peptides, method for assaying human pepsinogen II or human pepsin II, and assaying kit
AssigneeOno Pharmaceutical Co., Ltd.
InventorsAkio Hayashi, Masayoshi Matsuo
Life of this patent
Estimating the term…
Abstract
A peptide of the formula (I) (wherein each symbol is as defined in the description.) or an acid addition salt thereof. A compound of the formula (I) is a specific substrate for human pepsin II, so it can be used for assaying human pepsin II or human pepsinogen II and it is useful for diagnosis of gastric diseases such as gastric cancer and gastric ulcer.
Claims11
A peptide of the formula (I)
- wherein,
- Q is Qa—(AA)n—, wherein AA is L-amino acid, n is 0 or an integer of 1-15, Qa is hydrogen, C1-4 alkyl, an amino-protective group, D- or L-amino acid residue or NH2—(CH2)r—CO—, where r is an integer of 2-7,
- R1 and R2 are (i) hydrogen or halogen or, (ii) R1, R2 and an unsaturated bond together form an aromatic carbon ring that may be substituted by halogen,
- R3 is hydrogen or halogen,
- R4 is hydrogen, C1-3 alkyl or hydroxymethyl,
- EE is D- or L-amino acid,
- m is 0 or 1, and
- Z is an aniline derivative residue, an aminocoumarine derivative residue or an aminonaphthalene derivative residue,
- with the proviso that (I) when n is 2 or more, each AA is same or different, and that (2) the compounds wherein all of R1, R2 and R3 are hydrogen are excluded,
- or an acid addition salt thereof.
7 more elements
A peptide of the formula (I-A):
- wherein, each symbol is as defined in Table 1 (Tables 1-1˜1-4):
- TABLE 1 Definition of each symbol No. Q R4 (EE)m Z SEQ ID NO:
- (1) Pro Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:1 (2) Leu Ser 4-I-Phenyl H single bond p-NA SEQ ID NO:2 (3) Pro Gln Gln Ala 2-Naphthyl H single bond p-NA SEQ ID NO:3 (4) Pro Gln Gln Ala 4-I-Phenyl H single bond p-NA SEQ ID NO:4 (5) Pro Gln Gln Ala 4-Cl-Phenyl H single bond p-NA SEQ ID NO:5 (6) Pro Gln Gln Ala 2-Naphthyl Me single bond p-NA SEQ ID NO:6 (7) Pro Gln Gln Ala 4-I-Phenyl Me single bond p-NA SEQ ID NO:7 (8) Pro Gln Gln Ala 4-Cl-Phenyl Me single bond p-NA SEQ ID NO:8 (9) Pro Gln Gln Ala 2-Naphthyl Et single bond p-NA SEQ ID NO:9 (10) Pro Gln Gln Ala 4-I-Phenyl Et single bond p-NA SEQ ID NO:10 (11) Pro Gln Gln Ala 4-Cl-Phenyl Et single bond p-NA SEQ ID NO:11 (12) Pro Gln Gln Ala 2-Naphthyl n-Pr single bond p-NA SEQ ID NO:12 (13) Pro Gln Gln Ala 4-I-Phenyl n-Pr single bond p-NA SEQ ID NO:13 (14) Pro Gln Gln Ala 4-Cl-Phenyl n-Pr single bond p-NA SEQ ID NO:14 (15) Ac Lys Pro Gln Gln Ala 4-I-Phenyl Me single bond p-NA SEQ ID NO:15 (16) Leu Pro Gln Gln Ala 4-I-Phenyl Me single bond p-NA SEQ ID NO:16 (17) Asn Pro Gln Gln Ala 4-I-Phenyl Me single bond p-NA SEQ ID NO:17 (18) Gln Pro Gln Gln Ala 4-I-Phenyl Me single bond p-NA SEQ ID NO:18 (19) Ala Pro Gln Gln Ala 4-I-Phenyl Me single bond p-NA SEQ ID NO:19 (20) Val Pro Gln Gln Ala 4-I-Phenyl Me single bond p-NA SEQ ID NO:20 (21) Gly Pro Gln Gln Ala 4-I-Phenyl Me single bond p-NA SEQ ID NO:21 (22) Phe Pro Gln Gln Ala 4-I-Phenyl Me single bond p-NA SEQ ID NO:22 (23) Pro Gln Gln Asn 2-Naphthyl Me single bond p-NA SEQ ID NO:23 (24) Pro Gln Gln Gln 2-Naphthyl Me single bond p-NA SEQ ID NO:24 (25) Pro Gln Gln Gly 2-Naphthyl Me single bond p-NA SEQ ID NO:25 (26) Pro Gln Gln Met 2-Naphthyl Me single bond p-NA SEQ ID NO:26 (27) Pro Gln Gln Ser 2-Naphthyl Me single bond p-NA SEQ ID NO:27 (28) Pro Gln Gln Asp 2-Naphthyl Me single bond p-NA SEQ ID NO:28 (29) Pro Gln Gln Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:29 (30) Pro Gln Asn Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:30 (31) Pro Gln Ala Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:31 (32) Pro Gln Gly Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:32 (33) Pro Gln Leu Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:33 (34) Pro Gln Glu Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:34 (35) Pro Gln Asp Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:35 (36) Pro Gln Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:36 (37) Pro Asn Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:37 (38) Pro Ala Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:38 (39) Pro Val Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:39 (40) Pro Met Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:40 (41) Pro Ile Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:41 (42) Pro Gly Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:42 (43) Pro Glu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:43 (44) Pro Asp Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:44 (45) Pro Ser Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:45 (46) Pro Thr Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:46 (47) Asn Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:47 (48) Ala Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:48 (49) Val Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:49 (50) Met Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:50 (51) Ile Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:51 (52) Gly Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:52 (53) Leu Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:53 (54) Gln Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:54 (55) Lys Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:55 (56) Glu Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:56 (57) Ser Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:57 (58) Thr Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:58 (59) Tyr Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:59 (60) Ac Lys Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:60 (61) Pro Asn Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:61 (62) Ac Lys Asn Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:62 (63) Pro Ser Asn Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:63 (64) Pro Asn Asn Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:64 (65) Pro Gly Asn Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:65 (66) Ac Lys Ala Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:66 (67) β-Ala Asn Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:67 (68) Sar Asn Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:68 (69) Me-Val Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:69 (70) Me-Ala Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:70 (71) Sar Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:71 (72) Pro Leu Ser Glu 4-Cl-Phenyl Me single bond p-NA SEQ ID NO:72 (73) Pro Leu Ser Glu 3,4-DCP Me single bond p-NA SEQ ID NO:73 (74) Val Leu Ser Glu 4-Cl-Phenyl Me single bond p-NA SEQ ID NO:74 (75) D-Ala Asn Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:75 (76) D-Ala Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:76 (77) β-Ala Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:77 (78) γ-Abu Leu Ser Glu 2-Naphthyl Me single bond p-NA SEQ ID NO:78 (79) Leu Ser Glu 2-Naphthyl Me Leu p-NA SEQ ID NO:79 (80) Leu Ser Glu 2-Naphthyl Me Ala p-NA SEQ ID NO:80 (81) Leu Ser Glu 2-Naphthyl Me Gly p-NA SEQ ID NO:81 (82) Sar Leu Ser Glu 2-Naphthyl Me Ala p-NA SEQ ID NO:82 (83) Sar Leu Ser Glu 2-Naphthyl Me Gly p-NA SEQ ID NO:83 (84) Sar Leu Ser Glu 2-Naphthyl Me Ala m-ASD SEQ ID NO:84 (85) Sar Ser Gly 2-Naphthyl Me Ala DCHA SEQ ID NO:85
- in Table 1, the meaning of each abbreveated symbol is as follows:
- Me=methyl,
- Et=ethyl,
- n-Pr=n-propyl,
- Ac=acetyl,
- Sar=Nα-methyl-glycine,
- Me-Val=Nα-methyl-valine,
- Me-Ala=Nα-methyl-alanine,
- γ-Abu=γ-aminobutanoic acid,
- p-NA=p-nitroaniline residue,
- 3,4-DCP=3,4-dichlorophenyl,
- m-ASD=m-anisidine residue,
- DCHA=3,5-dichloro-4-hydroxyaniline residue.
13 more elements
Dependencies are inferred from the claim text.