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Nitrogen Containing Heterocyclic Compound

Abstract: ABSTRACT A compound represented by the general formula, or a salt thereof, has exceptional CXCL10 inhibitory activity and is useful as a treatment agent for the prevention and/or treatment, etc., of diseases involving overproduction of CXCL10. In the formula: R is a C|-s alky! group, etc.; R2 is a hydrogen atom, etc.; R3 is a halogen atom, etc.; ?}, "/}, and Z are CM, etc.; X is CONH, etc.; ring A is a phenyl group, etc.; R4 is a halogen atom, etc.; and m is an integer of 0-5.

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Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
12 February 2018
Publication Number
08/2018
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
Parent Application

Applicants

FUJIFILM Corporation
26-30, Nishiazabu 2-chome, Minato-ku, Tokyo 106-0031, Japan
TOYAMA CHEMICAL CO., LTD.
2-5, Nishishinjuku 3-chome, Shinjuku-ku, Tokyo 160-0023, Japan

Inventors

1. TANAKA, Tadashi
c/o TOYAMA CHEMICAL CO., LTD., Toyama Works, 4-1, Shimookui 2- chome, Toyama-shi, Toyama 930-8508, Japan
2. FUJINO, Masataka
c/o TOYAMA CHEMICAL CO., LTD., Toyama Works, 4-1, Shimookui 2- chome, Toyama-shi, Toyama 930-8508, Japan
3. FURUYA, Kentaro
c/o TOYAMA CHEMICAL CO., LTD., Toyama Works, 4-1, Shimookui 2- chome, Toyama-shi, Toyama 930-8508, Japan

Specification

A compound represented by the general formula [1] or a salt thereof:
wherein
R1 represents an optionally substituted Ci_6 alkyl group;
R2 represents a hydrogen atom, a halogen atom or an optionally substituted Ci-6 alkyl group;
R3 represents a halogen atom, an optionally substituted Ci.6 alkyl group, an optionally substituted
C2-6 alkenyl group, an optionally substituted C3.8 cycloalkyl group, an optionally substituted C4.g
cycloalkenyl group, an optionally substituted aryl group, an optionally substituted Ci.6 alkoxy
group, an optionally substituted Ci-6 alkylamino group, an optionally substituted di(Ci-6
alkyl)amino group or an optionally substituted heterocyclic group;
Z1, Z2 and Z3 are the same or different and each represent a nitrogen atom or a group represented
by the general formula CR5 wherein R5 represents a hydrogen atom, a halogen atom or an
optionally substituted Ci-6 alkyl group;
X1 represents
(1) a group represented by the general formula C(=0)N(R6) wherein the carbon atom is bonded to ring A, and R6 represents a hydrogen atom, an amino-protective group or an optionally substituted Ci_6 alkyl group,
(2) a group represented by the general formula N(R7)C(=0) wherein the nitrogen atom is bonded to ring A, and R7 represents a hydrogen atom, an amino-protective group or an optionally substituted Ci.6 alkyl group; or R7 represents, together with one substituent R4 on ring A, an optionally substituted C2.4 alkylene group, a group represented by the general formula O-Y wherein the oxygen atom is bonded to ring A, and Y1 represents an optionally substituted C1.3 alkylene group, a group represented by the general formula S(0)n- Y2 wherein the sulfur atom is bonded to ring A, Y2 represents an optionally substituted Ci_3 alkylene group, and n represents an integer of 0 to 2, or a group represented by the general formula N(R8)-Y3 wherein the nitrogen atom is bonded to ring A, Y represents an optionally substituted C1.3 alkylene group, and R represents a hydrogen atom, an amino-protective group, an optionally substituted C1.6 alkyl

group or an optionally substituted aryl group,
(3) an optionally substituted divalent cyclic hydrocarbon group resulting from the removal of one hydrogen atom from each of two adjacent atoms or
(4) an optionally substituted divalent heterocyclic group resulting from the removal of one hydrogen atom from each of two adjacent atoms;
ring A represents a cyclic hydrocarbon group or a heterocyclic group;
m number of R4 are the same or different and each represent a halogen atom, a cyano group, a
nitro group, an amino-protective group, an optionally substituted Ci.6 alkyl group, an optionally
substituted C2-6 alkenyl group, an optionally substituted C2-6 alkynyl group, an optionally
substituted C3.8 cycloalkyl group, an optionally substituted C4-g cycloalkenyl group, an optionally
substituted aryl group, an optionally substituted Ci.6 alkoxy group, an optionally substituted
aryloxy group, an optionally substituted Ci_6 alkylamino group, an optionally substituted di(Ci-6
alkyl)amino group, an optionally substituted arylamino group, an optionally substituted
carbamoyl group, an optionally substituted sulfamoyl group, an optionally substituted Ci-6
alkylthio group, an optionally substituted arylthio group, an optionally substituted Ci_6
alkylsulfonyl group, an optionally substituted arylsulfonyl group, an optionally substituted
heterocyclic group, an optionally protected amino group, an optionally protected hydroxyl group,
an optionally protected carboxyl group,
an optionally substituted C2-5 alkylene group formed together by two adjacent R ,
an optionally substituted C2-4 alkylene group formed together by one R4 and R',
a group represented by the general formula O-Y1 formed together by one R and R wherein the
oxygen atom is bonded to ring A, and Y1 represents an optionally substituted C1.3 alkylene
group,
a group represented by the general formula S(0)n-Y2 formed together by one R and R wherein
the sulfur atom is bonded to ring A, Y2 represents an optionally substituted C1-3 alkylene group,
and n represents an integer of 0 to 2, or
a group represented by the general formula N(R8)-Y3 formed together by one R and R wherein
the nitrogen atom is bonded to ring A, Y3 represents an optionally substituted C1.3 alkylene
group, and R8 represents a hydrogen atom, an amino-protective group, an optionally substituted
C1-6 alkyl group or an optionally substituted aryl group; and
m represents an integer of 0 to 5.
[Claim 2]
The compound according to claim 1 or a salt thereof, wherein R2 is a hydrogen atom or an optionally substituted Ci.6 alkyl group; and

eachofZ',Z2andZ3isCH. [Claim 3]
The compound according to claim 1 or 2 or a salt thereof, wherein R1 is a Ci-3 alkyl group, and
R3 is an optionally substituted Ci-6 alkyl group, an optionally substituted C3-s cycloalkyl group, an optionally substituted aryl group or an optionally substituted heterocyclic group. [Claim 4]
The compound according to any one of claims 1 to 3 or a salt thereof, wherein ring A is a cyclic hydrocarbon group. [Claim 5]
The compound according to any one of claims 1 to 4 or a salt thereof, wherein X is a group represented by the general formula C(=0)N(R6) wherein the carbon atom is bonded to ring A, and R6 represents a hydrogen atom, an amino-protective group or an optionally substituted Ci-6 alkyl group. [Claim 6]
The compound according to any one of claims 1 to 4 or a salt thereof, wherein X1 is a group represented by the general formula C(=0)N(R6a) wherein the carbon atom is bonded to ring A, and R6a represents a hydrogen atom or an optionally substituted Ci_3 alkyl group;
m number of R4 are the same or different and each are a halogen atom, an optionally substituted Ci_3 alkyl group, an optionally substituted C1-3 alkylamino group or an optionally protected amino group; and m is an integer of 0 to 2. [Claim 7]
The compound according to any one of claims 1 to 4 or a salt thereof, wherein R3 is an optionally substituted Cu6 alkyl group, an optionally substituted C3.8 cycloalkyl group or an optionally substituted heterocyclic group;
X1 is a group represented by the general formula C(=0)N(R6b) wherein the carbon atom is bonded to ring A, and R6b represents an optionally substituted C1-3 alkyl group; m number of R4 are the same or different and each are a halogen atom or an optionally substituted C1.3 alkyl group; and m is an integer of 0 to 2. [Claim 8]

m number of R4 are the same or different and each are a halogen atom; and m is an integer of 0 to 2. [Claim 9]
The compound according to any one of claims 1 to 4 or a salt thereof, wherein X1 is a group represented by the general formula N(R7)C(=0) wherein the nitrogen atom is bonded to ring A, and R7 represents a hydrogen atom, an amino-protective group or an optionally substituted Ci-6 alkyl group; or R7 represents, together with one substituent R4 on ring A, an optionally substituted C2^ alkylene group, a group represented by the general formula O-Y wherein the oxygen atom is bonded to ring A, and Y1 represents an optionally substituted C1-3 alkylene group, a group represented by the general formula S(0)n-Y2 wherein the sulfur atom is bonded to ring A, Y2 represents an optionally substituted C1-3 alkylene group, and n represents an integer of 0 to 2, or a group represented by the general formula N(R8)-Y3 wherein the nitrogen
o
atom is bonded to ring A, Y3 represents an optionally substituted C1.3 alkylene group, and R represents a hydrogen atom, an amino-protective group, an optionally substituted Ci.6 alkyl group or an optionally substituted aryl group. [Claim 10]
The compound according to any one of claims 1 to 4 or a salt thereof, wherein R3 is an optionally substituted Ci-6 alkyl group, an optionally substituted C3.8 cycloalkyl group or an optionally substituted heterocyclic group;
X1 is a group represented by the general formula N(R7a)C(=0) wherein the nitrogen atom is bonded to ring A, and R7a represents an optionally substituted C1-3 alkyl group, or R7a represents, together with one substituent R4 on ring A, an optionally substituted C2-3 alkylene group or a group represented by the general formula 0-Yla wherein the oxygen atom is bonded to ring A, and Yla represents an ethylene group;
m number of R4 are the same or different and each are a halogen atom, an optionally substituted C1-3 alkyl group, an optionally substituted C1-3 alkylsulfonyl group, an optionally substituted C2-3 alkylene group formed together by two adjacent R , an optionally substituted C2-3 alkylene group formed together by one R4 and R a, or a group represented by the general formula 0-Yla formed together by one R and R a wherein the oxygen atom is bonded to ring A, and Yla represents an ethylene group; and m is an integer of 0 to 2. [Claim 11]
The compound according to any one of claims 1 to 4 or a salt thereof, wherein R3 is an optionally substituted heterocyclic group;

X1 is a group represented by the general formula N(R7b)C(=0) wherein the nitrogen atom is
bonded to ring A, and R7b represents an optionally substituted C1.3 alkyl group, or R7b represents,
together with one substituent R4 on ring A, an optionally substituted C2-3 alkylene group;
m number of R4 are the same or different and each are an optionally substituted C1.3 alkyl group,
an optionally substituted C2-3 alkylene group formed together by two adjacent R , or
an optionally substituted C2-3 alkylene group formed together by one R4 and R7b; and
m is an integer of 0 to 2.
[Claim 12]
The compound according to claim 11 or a salt thereof, wherein X1 is a group represented by the general formula N(R7b)C(=0) wherein the nitrogen atom is bonded to ring A, and R7b represents an optionally substituted C1.3 alkyl group, or R7b represents, together with one substituent R4 on ring A, an optionally substituted C2-3 alkylene group; m number of R4 are the same or different and each are an optionally substituted C1-3 alkyl group, or
an optionally substituted C2-3 alkylene group formed together by one R4 and R7b; and m is an integer of 0 to 2. [Claim 13]
The compound according to any one of claims 1 to 4 or a salt thereof, wherein X is an optionally substituted divalent cyclic hydrocarbon group resulting from the removal of one hydrogen atom from each of two adjacent atoms or an optionally substituted divalent heterocyclic group resulting from the removal of one hydrogen atom from each of two adjacent atoms. [Claim 14]
The compound according to any one of claims 1 to 4 or a salt thereof, wherein R3 is an optionally substituted C1-6 alkyl group or an optionally substituted heterocyclic group; X1 is an optionally substituted divalent cyclic hydrocarbon group resulting from the removal of one hydrogen atom from each of two adjacent atoms or an optionally substituted divalent heterocyclic group resulting from the removal of one hydrogen atom from each of two adjacent atoms;
m number of R4 are the same or different and each are a halogen atom; and m is an integer of 0 to 2. [Claim 15]
The compound according to claim 14 or a salt thereof, wherein R3 is an optionally substituted heterocyclic group; and

X1 is an optionally substituted divalent heterocyclic group resulting from the removal of one hydrogen atom from each of two adjacent atoms. [Claim 16]
A pharmaceutical composition comprising a compound according to any one of claims 1 to 15 or a salt thereof. [Claim 17]
An agent for treatment of an immune disease, comprising a compound according to any one of claims 1 to 15 or a salt thereof.

Documents

Orders

Section Controller Decision Date
u/s 15 refused PRIYADHARSINI RAJANBABU 2021-02-24
u/s 15 refused PRIYADHARSINI RAJANBABU 2021-02-24

Application Documents

# Name Date
1 201847005128-STATEMENT OF UNDERTAKING (FORM 3) [12-02-2018(online)].pdf 2018-02-12
2 201847005128-PRIORITY DOCUMENTS [12-02-2018(online)].pdf 2018-02-12
3 201847005128-FORM 1 [12-02-2018(online)].pdf 2018-02-12
4 201847005128-DECLARATION OF INVENTORSHIP (FORM 5) [12-02-2018(online)].pdf 2018-02-12
5 201847005128-COMPLETE SPECIFICATION [12-02-2018(online)].pdf 2018-02-12
6 201847005128-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [12-02-2018(online)].pdf 2018-02-12
7 201847005128-Proof of Right (MANDATORY) [16-02-2018(online)].pdf 2018-02-16
8 201847005128-FORM-26 [16-02-2018(online)]_50.pdf 2018-02-16
9 201847005128-FORM-26 [16-02-2018(online)].pdf 2018-02-16
10 Correspondence by Agent_Form1, Power of Attorney_20-02-2018.pdf 2018-02-20
11 201847005128-FORM 3 [30-06-2018(online)].pdf 2018-06-30
12 201847005128-FORM 3 [16-11-2018(online)].pdf 2018-11-16
13 201847005128-certified copy of translation (MANDATORY) [16-11-2018(online)].pdf 2018-11-16
14 201847005128-PA [29-03-2019(online)].pdf 2019-03-29
15 201847005128-ASSIGNMENT DOCUMENTS [29-03-2019(online)].pdf 2019-03-29
16 201847005128-8(i)-Substitution-Change Of Applicant - Form 6 [29-03-2019(online)].pdf 2019-03-29
17 Correspondence by Agent_Power of Attorney And English Translation_02-04-2019.pdf 2019-04-02
18 201847005128-Proof of Right (MANDATORY) [15-04-2019(online)].pdf 2019-04-15
19 201847005128-FORM 3 [17-05-2019(online)].pdf 2019-05-17
20 201847005128-FORM 18 [04-06-2019(online)].pdf 2019-06-04
21 201847005128-FORM 3 [03-12-2019(online)].pdf 2019-12-03
22 201847005128-FORM 3 [30-05-2020(online)].pdf 2020-05-30
23 201847005128-FER.pdf 2020-06-30
24 201847005128-OTHERS [31-08-2020(online)].pdf 2020-08-31
25 201847005128-FER_SER_REPLY [31-08-2020(online)].pdf 2020-08-31
26 201847005128-CLAIMS [31-08-2020(online)].pdf 2020-08-31
27 201847005128-Annexure [31-08-2020(online)].pdf 2020-08-31
28 201847005128-FORM 3 [04-12-2020(online)].pdf 2020-12-04
29 201847005128-REQUEST FOR ADJOURNMENT OF HEARING UNDER RULE 129A [20-01-2021(online)].pdf 2021-01-20
30 201847005128-Correspondence to notify the Controller [12-02-2021(online)].pdf 2021-02-12
31 201847005128-US(14)-HearingNotice-(HearingDate-25-01-2021).pdf 2021-10-17
32 201847005128-US(14)-ExtendedHearingNotice-(HearingDate-24-02-2021).pdf 2021-10-17

Search Strategy

1 SearchStratogy-SureChEMBLE_30-06-2020.pdf