Sign In to Follow Application
View All Documents & Correspondence

Cyclic Peptide, Affinity Chromatography Support, Labeled Antibody, Antibody Drug Conjugate, And Pharmaceutical Preparation

Abstract: ABSTRACT Provided is a cyclic peptide, which is represented by Formula (I) or Formula (I") and has excellent antibody binding properties and improved chemical resistance, an affinity chromatography support, a labeled antibody, an antibody drug conjugate, and a pharmaceutical preparation. ^-Xg^Xi-X^Xm-X"-X^X^Xn-X^Xjlk-Xh-R0 - (I) In Formula (I), Xa and Xb each independently represent an amino acid residue derived from an amino acid, other than L-cysteine and D-cysteine, having a thiol group on a side chain and are bonded to each other through a disulfide bond, or, one of Xa and Xb represents an amino acid residue derived from an amino acid, other than L-cysteine and D-cysteine, having a thiol group on a side chain and the other represents an amino acid residue derived from an amino acid having a haloacetyl group on a side chain, and Xa and Xb are bonded to each other through a thioether bond. RN-Xg-[Xi-Xa-Xm-X1-X2-X3-Xn-Xb-XJ]k-Xh-Rc - (I") In Formula (T), one of Xa and Xb represents an amino acid residue derived from L-cysteine or D-cysteine and the other represents an amino acid residue derived from an amino acid having a haloacetyl group on a side chain, and Xa and Xb are bonded to each other through a thioether bond, or, one of Xa and Xb represents an amino acid residue derived from L-penicillamine or D-penicillamine and the other represents an amino acid residue derived from an amino acid having a haloacetyl group on a side chain, and Xa and Xb are bonded to each other through a thioether bond.

Get Free WhatsApp Updates!
Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
19 April 2018
Publication Number
18/2018
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
Parent Application

Applicants

FUJIFILM Corporation
26-30,Nishiazabu 2-chome, Minato-ku, Tokyo 106-8620

Inventors

1. MINAMI, Koichi
c/o FUJIFILM Corp oration, 577, Ushij ima, Kaisei-machi, Ashigara-kamigun, Kana gawa 258-8577

Specification

OUR PROPOSED CLAIM AMENDMENT (CLEAN-UP VERSION)
1. A cyclic peptide represented by Formula (I),
RN-Xg- [ X1-Xa-Xm-X1-X2-X3-Xn-Xb-X j ] k-Xh-Rc - (I) :
in Formula (I),
RN represents an N-terminal group;
Rc represents a C-terminal group;
X1 represents an L-leucine residue, an L-isoleucine residue, an L-methionine residue, an L-lysine residue, or an L-arginine residue;
X2 represents an L-valine residue or an L-isoleucine residue;
X3 represents an L-tryptophan residue;
Xa and Xb each independently represent an amino acid residue derived from an amino acid, other than L-cysteine and D-cysteine, having a thiol group on a side chain, and are bonded to each other through a disulfide bond, or, one of Xa and Xb represents an amino acid residue derived from an amino acid, other than L-cysteine and D-cysteine, having a thiol group on a side chain, and the other represents an amino acid residue derived from an amino acid having a haloacetyl group on a side chain, and Xa and Xb are bonded to each other through a thioether bond;
Xg, Xh, Xi, Xj, Xm, and Xn each represent g consecutive X's, h consecutive X's, i consecutive X's, j consecutive X's, m consecutive X's, and n consecutive X's;
X represents an amino acid residue, and in a case where there is a plurality of X's, the plurality of X's may be the same as or different from each other;
g, h, i, and j each independently represent an integer egual to or greater than 0;
m and n are integers satisfying 0 < m < 9, 0 < n < 9, and 3 < m + n < 9 simultaneously; and
k is an integer egual to or greater than 1, and in a case
where k > 2, X1, X2, X3, Xa, Xb, X±, Xj, Xm, and Xn in a repeating unit [X1-Xa-Xm-X1-X2-X3-Xn-Xb-Xj] each may be the same or different

between the repeating units.
2. The cyclic peptide according to claim 1 that is represented
by Formula (IA),
R -Xg-[XP2-X r—Xpi—X —Xm—X -X -X —Xn—X -Xqi-X S-Xq2] k-Xh-R — (IA) :
in Formula (IA),
RN, Rc, X1, X2, X3, Xa, Xb, Xg, Xh, Xm, Xn, X, g, h, m, n, and k have the same definitions as those in Formula (I);
X4r, X5S, Xpi, Xp2, Xqi, and Xq2 each represent r consecutive X4's, s consecutive X5's, pi consecutive X's, p2 consecutive X's, gl consecutive X's, and g2 consecutive X's;
X4 and X5 each independently represent an amino acid residue derived from an amino acid having a carboxy group on a side chain or an amino acid residue derived from an amino acid having a hydroxy group on a side chain, and in a case where there is a plurality of X4's or X5's, the plurality of X4's or X5's may be the same as or different from each other;
pi, p2, gl, and g2 each independently represent an integer egual to or greater than 0;
r and s each represent an integer satisfying 0 < r < 5, 0 < s < 5, and 1 < Max (r,s) < 5, where Max (r,s) represents a larger one between two numbers represented by r and s in a case where r
■$■ s and represents r or s in a case where r = s; and
in a case where k > 2, X1, X2, X3, Xa, Xb, X4r, X5S, Xm, Xn, Xp2, Xpi, Xql, and Xq2 in a repeating unit [Xp2-X4r-Xpl-Xa-Xm-X1-X2-X3-Xn-Xb-Xqi-X5s-Xq2] each may be the same or different between the repeating units.
3. The cyclic peptide according to claim 1 that is represented
by Formula (IB),
R —Xvl—X t—Xv2—[Xi~X —Xm—X —X —X —Xn—X —Xj]^—Xw2—X u—Xwl—R ••• (IB) :
in Formula (IB),
R, R, X, X, X, X, X, Xi, Xj, Xm, Xn, X, l, j, m, n, and k have the same definitions as those in Formula (I);
X6t, X7U, Xvi, Xv2, X„i, and Xw2 each represent t consecutive X6's, u consecutive X7's, vl consecutive X's, v2

consecutive X's, wl consecutive X's, and w2 consecutive X's;
X6 and X7 each independently represent an amino acid residue derived from an amino acid having an immobilizing functional group on a side chain, and in a case where there is a plurality of X6's or X7's, the plurality of X6's or X7's may be the same as or different from each other;
t and u each represent an integer satisfying 0 < t < 5, 0 < u < 5, and 1 < Max (t,u) < 5, where Max (t,u) represents a larger one between two numbers represented by t and u in a case where t
^ u and represents t or u in a case where t = u;
vl, v2, wl, and w2 each independently represent an integer egual to or greater than 0; and
in a case where k > 2, X1, X2, X3, Xa, Xb, X±, Xj, Xm, and Xn in a repeating unit [X1-Xa-Xm-X1-X2-X3-Xn-Xb-Xj] each may be the same or different between the repeating units.
4. The cyclic peptide according to any one of claims 1 to 3 that is represented by Formula (IC),
R
W v" v v rv v v va v v v v v v v v v 1 v
—Avl — A t—Av2 — LAp2— A r—Api— A —Am—A —A —A —An—A —Aqi"A s— Aq2 J k~Aw2~
X u—Xwi—R ••• (IC) :
in Formula (IC),
RN, Rc, X1, X2, X3, Xa, Xb, Xm, Xn, X, m, n, and k have the same definitions as those in Formula (I);
Xpi, XP2, Xqi, Xq2, X r, X s, X t, X u, Xvi, Xv2, Xwi, and XW2 each represent pi consecutive X's, p2 consecutive X's, gl consecutive X's, g2 consecutive X's, r consecutive X4's, s consecutive X5's, t consecutive X6's, u consecutive X7's, vl consecutive X's, v2 consecutive X's, wl consecutive X's, and w2 consecutive X's';
X4 and X5 each independently represent an amino acid residue derived from an amino acid having a carboxy group on a side chain or an amino acid residue derived from an amino acid having a hydroxy group on a side chain, and in a case where there is a plurality of X4's or X5's, the plurality of X4's or X5's may be the same as or different from each other;
X6 and X7 each independently represent an amino acid residue derived from an amino acid having an immobilizing

functional group on a side chain, and in a case where there is a plurality of X6 or X7, the plurality of X6's or X7's may be the same as or different from each other;
pi, p2, ql, and q2 each independently represent an integer equal to or greater than 0;
r and s each represent an integer satisfying 0 < r < 5, 0 < s < 5, and 1 < Max (r,s) < 5, where Max (r,s) represents a larger one between two numbers represented by r and s in a case where r
^ s and represents r or s in a case where r = s;
t and u each represent an integer satisfying 0 < t < 5, 0 < u < 5, and 1 < Max (t,u) < 5, where Max (t,u) represents a larger one between two numbers represented by t and u in a case where t
^ u and represents t or u in a case where t = u;
vl, v2, wl, and w2 each independently represent an integer equal to or greater than 0; and
in a case where k > 2, X1, X2, X3, Xa, Xb, X4r, X5S, Xm, Xn, Xp2, Xpi, Xqi, and Xq2 in a repeating unit [Xpz-X^-Xpi-X^Xm-X^X^X3-Xn-Xb-Xqi-X5s-Xq2] each may be the same or different between the repeating units.
5_. A cyclic peptide represented by Formula (Ir),
RN-Xg-[X1-Xa-Xm-X1-X2-X3-Xn-Xb-Xj]k-Xh-Rc - (i'):
in Formula (Ir),
RN represents an N-terminal group;
Rc represents a C-terminal group;
X1 represents an L-leucine residue, an L-isoleucine residue, an L-methionine residue, an L-lysine residue, or an L-arginine residue;
X2 represents an L-valine residue or an L-isoleucine residue;
X3 represents an L-tryptophan residue;
one of Xa and Xb represents an amino acid residue derived from L-cysteine or D-cysteine and the other represents an amino acid residue derived from an amino acid having a haloacetyl group on a side chain, and Xa and Xb are bonded to each other through a thioether bond, or, one of Xa and Xb represents an amino acid

residue derived from L-penicillamine or D-penicillamine, and the other represents an amino acid residue derived from an amino acid having a haloacetyl group on a side chain, and Xa and Xb are bonded to each other through a thioether bond;
Xg, Xh, Xi, Xj, Xm, and Xn each represent g consecutive X's, h consecutive X's, i consecutive X's, j consecutive X's, m consecutive X's, and n consecutive X's;
in a case where one of Xa and Xb represents an amino acid residue derived from L-cysteine or D-cysteine, X represents an amino acid residue derived from an amino acid other than L-serine, D-serine, L-homoserine, D-homoserine, L-arginine, and D-arginine,
in a case where one of Xa and Xb represents an amino acid residue derived from L-penicillamine or D-penicillamine, X represents an amino acid residue derived from an amino acid other than L-serine and D-serine, and
in a case where there is a plurality of X's, the plurality of X's may be the same as or different from each other;
g, h, i, and j each independently represent an integer egual to or greater than 0;
m and n are integers satisfying 0 < m < 9, 0 < n < 9, and 3 < m + n < 9 simultaneously; and
k is an integer egual to or greater than 1, and in a case
where k > 2, X1, X2, X3, Xa, Xb, X±, Xj, Xm, and Xn in a repeating unit [X1-Xa-Xm-X1-X2-X3-Xn-Xb-Xj] each may be the same or different between the repeating units.
6 . The cyclic peptide according to claim 5 that is represented by Formula (l'A),
R -Xg-[XP2-X r—Xpi—X —Xm—X -X -X —Xn—X -Xqi-X S-Xq2] k-Xh-R — (I A) :
in Formula (l'A),
RN, Rc, X1, X2, X3, Xa, Xb, Xg, Xh, Xm, Xn, g, h, m, n, and k
have the same definitions as those in Formula (i');
X4r, X5S, Xpi, Xp2, Xqi, and Xq2 each represent r consecutive X4's, s consecutive X5's, pi consecutive X's, p2 consecutive X's, gl consecutive X's, and g2 consecutive X's;
in a case where one of Xa and Xb represents an amino acid

residue derived from L-cysteine or D-cysteine, X represents an amino acid residue derived from an amino acid other than L-serine, D-serine, L-homoserine, D-homoserine, L-arginine, and D-arginine,
in a case where one of Xa and Xb represents an amino acid residue derived from L-penicillamine or D-penicillamine, X represents an amino acid residue derived from an amino acid other than L-serine and D-serine, and
in a case where there is a plurality of X's, the plurality of X's may be the same as or different from each other;
in a case where one of Xa and Xb represents an amino acid residue derived from L-cysteine or D-cysteine, X4 and X5 each independently represent an amino acid residue derived from an amino acid having a carboxy group on a side chain or an amino acid residue derived from an amino acid, other than L-serine, D-serine, L-homoserine, and D-homoserine, having a hydroxy group on a side chain,
in a case where one of Xa and Xb represents an amino acid residue derived from L-penicillamine or D-penicillamine, X4 and X5 each independently represent an amino acid residue derived from an amino acid having a carboxy group on a side chain or an amino acid residue derived from an amino acid, other than L-serine or D-serine, having a hydroxy group on a side chain, and
in a case where there is a plurality of X4's or X5's, the plurality of X4's or X5's may be the same as or different from each other;
pi, p2, gl, and g2 each independently represent an integer egual to or greater than 0;
r and s each represent an integer satisfying 0 < r < 5, 0 < s < 5, and 1 < Max (r,s) < 5, where Max (r,s) represents a larger one between two numbers represented by r and s in a case where r ^ s and represents r or s in a case where r = s; and
in a case where k > 2, X1, X2, X3, Xa, Xb, X4r, X5S, Xm, Xn, Xp2, Xpi, Xqi, and Xq2 in a repeating unit [Xp2-X4r-Xpi-Xa-Xm-X1-X2-X3-Xn-Xb-Xqi-X5s-Xq2] each may be the same or different between the repeating units.

1_. The cyclic peptide according to claim .5 that is represented
by Formula (l'B),
R —Xvi—X t_XV2~ [Xi—X —Xm—X -X -X —Xn—X -Xj] k-XW2-X u—Xwi—R ••• (IB):
in Formula (l'B),
RN, Rc, X1, X2, X3, Xa, Xb, X±, Xj, Xm, Xn, i, j, m, n, and k
have the same definitions as those in Formula (i');
X6t, X7U, xvi, Xv2, X„i, and Xw2 each represent t consecutive X6's, u consecutive X7's, vl consecutive X's, v2 consecutive X's, wl consecutive X's, and w2 consecutive X's;
in a case where one of Xa and Xb represents an amino acid residue derived from L-cysteine or D-cysteine, X represents an amino acid residue derived from an amino acid other than L-serine, D-serine, L-homoserine, D-homoserine, L-arginine, and D-arginine,
in a case where one of Xa and Xb represents an amino acid residue derived from L-penicillamine or D-penicillamine, X represents an amino acid residue derived from an amino acid other than L-serine and D-serine, and
in a case where there is a plurality of X's, the plurality of X's may be the same as or different from each other;
in a case where one of Xa and Xb represents an amino acid residue derived from L-cysteine or D-cysteine, X6 and X7 each independently represent an amino acid residue derived from an amino acid, other than L-serine, D-serine, L-homoserine, D-homoserine, L-arginine, and D-arginine, having an immobilizing functional group on a side chain or each independently represent an amino acid residue derived from an amino acid having an immobilizing functional group on a side chain,
in a case where one of Xa and Xb represents an amino acid residue derived from L-penicillamine or D-penicillamine, X6 and X7 each independently represent an amino acid residue derived from an amino acid, other than L-serine and D-serine, having an immobilizing functional group on a side chain, and
in a case where there is a plurality of X6's or X7's, the plurality of X6's or X7's may be the same as or different from each other;
t and u each represent an integer satisfying 0 < t < 5, 0 <

u < 5, and 1 < Max (t,u) < 5, where Max (t,u) represents a larger one between two numbers represented by t and u in a case where t
^ u and represents t or u in a case where t = u;
vl, v2, wl, and w2 each independently represent an integer egual to or greater than 0; and
in a case where k > 2, X1, X2, X3, Xa, Xb, X±, Xj, Xm, and Xn in a repeating unit [X1-Xa-Xm-X1-X2-X3-Xn-Xb-Xj] each may be the same or different between the repeating units.
_8. The cyclic peptide according to any one of claims 5_ to 1_ that is represented by Formula (l'C),
RN \r -w-6 TT r \r -w-4 TT -w-a \r yl V" V V V V V V 1 V
Avl A t Av2 L Ap2 A r Apl A Am A A A An A Aql A s Aq2 J k Aw2
X u—Xwi—R ••• (I C) :
in Formula (l'C),
RN, Rc, X1, X2, X3, Xa, Xb, Xm, Xn, m, n, and k have the same
definitions as those in Formula (Ir) ;
Xpi, Xp2, ^qi/ Xq2? X r, X s, X t, X u, Xvi, Xv2, Xwi, and XW2 each represent pi consecutive X's, p2 consecutive X's, gl consecutive X's, g2 consecutive X's, r consecutive X4's, s consecutive X5's, t consecutive X6's, u consecutive X7's, vl consecutive X's, v2 consecutive X's, wl consecutive X's, and w2 consecutive X's;
in a case where one of Xa and Xb represents an amino acid residue derived from L-cysteine or D-cysteine, X represents an amino acid residue derived from an amino acid other than L-serine, D-serine, L-homoserine, D-homoserine, L-arginine, and D-arginine,
in a case where one of Xa and Xb represents an amino acid residue derived from L-penicillamine or D-penicillamine, X represents an amino acid residue derived from an amino acid other than L-serine and D-serine, and
in a case where there is a plurality of X's, the plurality of X's may be the same as or different from each other;
in a case where one of Xa and Xb represents an amino acid residue derived from L-cysteine or D-cysteine, X4 and X5 each independently represent an amino acid residue derived from an amino acid having a carboxy group on a side chain or an amino acid residue derived from an amino acid, other than L-serine, D-

serine, L-homoserine, and D-homoserine, having a hydroxy group on a side chain,
in a case where one of Xa and Xb represents an amino acid residue derived from L-penicillamine or D-penicillamine, X4 and X5 each independently represent an amino acid residue derived from an amino acid having a carboxy group on a side chain or an amino acid residue derived from an amino acid, other than L-serine and D-serine, having a hydroxy group on a side chain, and
in a case where there is a plurality of X4's or X5's, the plurality of X4's or X5's may be the same as or different from each other;
in a case where one of Xa and Xb represents an amino acid residue derived from L-cysteine or D-cysteine, X6 and X7 each independently represent an amino acid residue derived from an amino acid, other than L-serine, D-serine, L-homoserine, D-homoserine, L-arginine, and D-arginine, having an immobilizing functional group on a side chain or each independently represent an amino acid residue derived from an amino acid having an immobilizing functional group on a side chain,
in a case where one of Xa and Xb represents an amino acid residue derived from L-penicillamine or D-penicillamine, X6 and X7 each independently represent an amino acid residue derived from an amino acid, other than L-serine and D-serine, having an immobilizing functional group on a side chain, and
in a case where there is a plurality of X6's or X7's, the plurality of X6's or X7's may be the same as or different from each other;
pi, p2, gl, and g2 each independently represent an integer egual to or greater than 0;
r and s each represent an integer satisfying 0 < r < 5, 0 < s < 5, and 1 < Max (r,s) < 5, where Max (r,s) represents a larger one between two numbers represented by r and s in a case where r ^ s and represents r or s in a case where r = s;
t and u each represent an integer satisfying 0 < t < 5, 0 < u < 5, and 1 < Max (t,u) < 5, where Max (t,u) represents a larger one between two numbers represented by t and u in a case where t

■$■ u and represents t or u in a case where t = u;
vl, v2, wl, and w2 each independently represent an integer equal to or greater than 0; and
in a case where k > 2, X1, X2, X3, Xa, Xb, X4r, X5S, Xm, Xn,
Xp2, Xpi, Xqi, and Xq2 in a repeating unit [Xpz-X^-X^-X^-X^X^-X2^3-
Xn-Xb-Xqi-X5s-Xq2] each may be the same or different between the
repeating units.
_9. The cyclic peptide according to any one of claims 1 to 8 that is an antibody binding ligand.
10. The cyclic peptide according to any one of claims 1 to 8 that is a linker for labeling antibodies.

Documents

Application Documents

# Name Date
1 201847014891-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [19-04-2018(online)].pdf 2018-04-19
2 201847014891-STATEMENT OF UNDERTAKING (FORM 3) [19-04-2018(online)].pdf 2018-04-19
3 201847014891-SEQUENCE LISTING(PDF) [19-04-2018(online)].pdf 2018-04-19
4 201847014891-SEQUENCE LISTING [19-04-2018(online)].jpg 2018-04-19
5 201847014891-REQUEST FOR EXAMINATION (FORM-18) [19-04-2018(online)].pdf 2018-04-19
6 201847014891-PROOF OF RIGHT [19-04-2018(online)].pdf 2018-04-19
7 201847014891-PRIORITY DOCUMENTS [19-04-2018(online)].pdf 2018-04-19
8 201847014891-POWER OF AUTHORITY [19-04-2018(online)].pdf 2018-04-19
9 201847014891-FORM 18 [19-04-2018(online)].pdf 2018-04-19
10 201847014891-FORM 18 [19-04-2018(online)]-1.pdf 2018-04-19
11 201847014891-FORM 1 [19-04-2018(online)].pdf 2018-04-19
12 201847014891-DECLARATION OF INVENTORSHIP (FORM 5) [19-04-2018(online)].pdf 2018-04-19
13 201847014891-COMPLETE SPECIFICATION [19-04-2018(online)].pdf 2018-04-19
14 201847014891-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [19-04-2018(online)].pdf 2018-04-19
15 Correspondence by Agent_Form 1_27-04-2018.pdf 2018-04-27
16 201847014891-FORM 3 [04-06-2018(online)].pdf 2018-06-04
17 201847014891-SEQUENCE LISTING [30-09-2021(online)].txt 2021-09-30
18 201847014891-OTHERS [30-09-2021(online)].pdf 2021-09-30
19 201847014891-FORM 3 [30-09-2021(online)].pdf 2021-09-30
20 201847014891-FER_SER_REPLY [30-09-2021(online)].pdf 2021-09-30
21 201847014891-COMPLETE SPECIFICATION [30-09-2021(online)].pdf 2021-09-30
22 201847014891-CLAIMS [30-09-2021(online)].pdf 2021-09-30
23 201847014891-ABSTRACT [30-09-2021(online)].pdf 2021-09-30
24 201847014891-FER.pdf 2021-10-17
25 201847014891-US(14)-HearingNotice-(HearingDate-13-11-2023).pdf 2023-10-31
26 201847014891-Correspondence to notify the Controller [09-11-2023(online)].pdf 2023-11-09

Search Strategy

1 SearchE_30-03-2021.pdf