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NZ737408B2 - Antibacterial compounds - Google Patents

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Publication number
NZ737408B2
NZ737408B2 NZ737408A NZ73740816A NZ737408B2 NZ 737408 B2 NZ737408 B2 NZ 737408B2 NZ 737408 A NZ737408 A NZ 737408A NZ 73740816 A NZ73740816 A NZ 73740816A NZ 737408 B2 NZ737408 B2 NZ 737408B2
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NZ
New Zealand
Prior art keywords
ring
alkyl
optionally substituted
compound
halo
Prior art date
Application number
NZ737408A
Other versions
NZ737408A (en
Inventor
Jerome Emile Georges Guillemont
Magali Madeleine Simone Motte
Pierre Jean Marie Bernard Raboisson
Abdellah Tahri
Original Assignee
Janssen Sciences Ireland Uc
Filing date
Publication date
Application filed by Janssen Sciences Ireland Uc filed Critical Janssen Sciences Ireland Uc
Priority to NZ774761A priority Critical patent/NZ774761B2/en
Priority claimed from PCT/EP2016/065499 external-priority patent/WO2017001660A1/en
Publication of NZ737408A publication Critical patent/NZ737408A/en
Publication of NZ737408B2 publication Critical patent/NZ737408B2/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/429—Thiazoles condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/438—The ring being spiro-condensed with carbocyclic or heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A61P31/06—Antibacterial agents for tuberculosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Abstract

The present invention relates to the following compounds, wherein the integers are as defined in the description, and where the compounds may be useful as medicaments, for instance for use in the treatment of tuberculosis.

Claims (25)

1. Use of a compound of formula (IA) in the manufacture of a medicament for the treatment of tuberculosis ring A ring B wherein R represents hydrogen; L represents -CH -; 10 X represents an optional phenylene or naphthylene aromatic linker group, which linker group may itself be optionally substituted by one or more substituents selected from fluoro, -OH, -OC alkyl and C alkyl, wherein the latter two alkyl moieties are 1-6 1-6 themseleves optionally substituted by one or more fluoro atoms; 15 X represents C(H) or N; b 2 2 X represents C(H), N, or O, in which case L is not present, or C=O, in which case L is also not present; q represents -CH -, -CH -CH -, –O-CH - or “-”; 2 2 2 2 20 q represents -CH - or -CH -CH -; 2 2 2 q represents -CH - or -CH -CH -; 2 2 2 q represents -CH - or -CH -CH -; 2 2 2 when X represents O or C=O, then L is not present; b 2 f g 25 when X represents C(H) or N, then L may represent hydrogen, halo, -OR , -C(O)-R , C1-6 alkyl optionally substituted by one or more halo, e.g. fluoro atoms, or an aromatic group optionally substituted by one or more substituents selected from halo, C alkyl which is optionally substituted by one or more substituents selected from fluoro, -CF and/or -SF , -OC alkyl which is optionally substituted by one or more fluoro atoms, - 5 1-6 30 O-phenyl which is optionally substituted by halo, C alkyl, C fluoroalkyl and/or - 1-6 1-6 OC alkyl) or –SF ; or, when attached to nitrogen, i.e. when X is N, L represents – 1-6 5 S(O) -C alkyl optionally substituted by one or more fluoro atoms; 2 1-6 R represents hydrogen, C alkyl optionally substituted by one or more fluoro or an 5 aromatic group which is optionally substituted by one or more substituents selected from halo, C1-6alkyl and -OC1-6alkyl, where the latter two alkyl moieties may themseleves be optionally substituted by one or more fluoro atoms; R represents hydrogen or C alkyl optionally substituted by one or more substituents 10 selected from fluoro, or -OC alkyl, which latter moiety is also optionally substuituted by one or more fluoro atoms or an aromatic group optionally substituted by one or more substituents selected from halo, C alkyl or -OC alkyl; 1-6 1-6 ring A may be attached to the –C(O)-N(R )- moiety via either one of two possible 15 bonds represented by the dotted lines, which bonds are linked to ring A at two different atoms of that ring; ring A is a 5-membered aromatic ring containing at least one heteroatom, and preferably containing at least one nitrogen atom; ring B is a 5- or 6-membered ring, which may be aromatic or non-aromatic, optionally containing one to four heteroatoms, preferably selected from nitrogen, oxygen and sulfur; 25 either ring A and/or ring B may be optionally substituted by one or more substituents selected from: halo, C alkyl optionally substituted by one or more halo, e.g. fluoro atoms and/or -OC alkyl which is optionally substituted by one or more fluoro atoms, or a pharmaceutically-acceptable salt thereof.
2. The use as claimed in Claim 1, wherein X represents in which such linker groups are optionally substituted by one or more substituents selected from fluoro, CH , CF , -OCH and –OCF .
3. 3 3 3 5 3. The use as claimed in Claim 1 or 2, wherein the spiro-cyclic moiety, i.e. the combined X and X -containing ring is represented as follows:
4. The use as claimed in any one of the preceding claims wherein: ring A is represented as follows: ; and/or ring B is represented as follows: wherein “SUB” and “Sub” represent one or more possible substituents on the relevant atom, e.g. carbon or nitrogen atom, wherein the substituents are as defined in claim 1.
5. The use as claimed in any one of the preceding claims, wherein the combined ring systems, i.e. Ring A and Ring B is represented as follows: where “SUB” represents one or more possible substituents on the bicycle, i.e. on ring A 5 and/or on ring B, and “Sub” represents a possible optional substituent on the N atom of the bicycle, wherein the substituents are as defined in claim 1 and unsubstituted in this context would mean NH.
6. The use as claimed in any one of the preceding claims, wherein: 10 at least one of X and X represents N and the other represents C(H), N or, in the case of X , O; and/or both X and X do not represent C(H).
7. The use as claimed in any one of the preceding claims, wherein L represents 15 hydrogen, halo, -OR , -C(O)R , or an aromatic group optionally substituted by one or two substituents selected from – 20 OC alkyl which isoptionally substituted by one or more fluoro atoms or –SF , or, 1-6 5 alternatively by halo.
8. The use as claimed in Claim 7, wherein R represents C alkyl or an aryl group optionally substituted by C alkyl which is 1-6 1-3 optionally substituted by one or more fluoro atoms, so forming a -CF group,and/or 5 R represents C1-3alkyl, optionally substituted by fluoro, or phenyl.
9. The use as claimed in any one of Claims 1-6, wherein when X is N and L represents -S(O) -C alkyl, then it represents -S(O) CF . 2 1-6 2 3
10. 10. The use as claimed in any one of Claims 1-9, wherein the medicament is in a combination with one or more other anti-tuberculosis agents.
11. The use as claimed in Claim 10, wherein the combination is a combined preparation for simultaneous, separate or sequential use.
12. A compound of formula (IA) as defined in Claim 1 but wherein: L represents –CH -; X is not present or X represents a carbocyclic aromatic linker group; when X represents a carbocyclic linker group it represents phenylene, e.g. a 1,4- 20 phenylene, for instance: at least one of X and X represents N and the other represents C(H), N or, in the case of X , O; the X and X -containing spiro-cycle 3- to 6-membered ring attached to a 4- to 6- 25 membered ring; in one aspect L represents an optionally substituted aromatic group, which may be phenyl or a 5- or 6-membered heterocyclic group, e.g. containing at least one nitrogen atom, so forming a pyridyl, thiazolyl or triazolyl ring; optionally the heterocyclic group is a pyridyl, where the optional substituents on aromatic L groups are selected from 30 halo, C alkyl, -CF , -OC alkyl and -OCF ; and/or 1-6 3 1-6 3 R represents an aryl group, preferably phenyl, optionally substituted by C alkyl, which is optionally substituted by fluoro; ring A and ring B together represent a 8 or 9-membered bicyclic ring, ring A is a 5- membered ring and ring B may be a 5 or 6-membered ring, in which both rings are 35 preferably aromatic, containing at least one nitrogen atom, preferably at least one nitogen atom that is common to both rings; optional substituents on ring A and ring B are halo, C alkyl and -OC alkyl, 1-3 1-3 or a pharmaceutically-acceptable salt thereof. 5
13. A compound of formula (IB) as depicted below: ring B ring A wherein the variables are as defined in any one of Claims 1-10, and where: n1, n2, n3 and n4 independently represent 1; 10 at least one of X and X represents N and the other represents CH or N.
14. A compound as claimed in Claim 13, of the following formula: ring B ring A wherein 15 R represents hydrogen; L represents –CH -; X represents a carbocyclic aromatic linker group that is: a 1,4-phenylene: 20 at least one of X and X represents N and the other represents CH or N; L represents –S(O) -C alkyl optionally substituted by one or more fluoro atoms, e.g. 2 1-6 forming –S(O) CF ; the combined ring systems, i.e. Ring A and Ring B are represented as follows: and “SUB” represents optional substituents on ring A and ring B are halo, C alkyl and -OC alkyl, or a pharmaceutically-acceptable salt thereof.
15. The compound: or a pharmaceutically-acceptable salt thereof.
16. A compound as defined in any one of Claims 12-15, for use as a pharmaceutical.
17. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and, as active ingredient, a therapeutically effective amount of a compound as defined 20 in any one of Claims 12-15.
18. Compound according to any one of Claims 12-15 for use in the treatment of tuberculosis. 25
19. Use of a compound according to any one of claims 12 to 15 in the manufacture of a medicament for the treatment of tuberculosis.
20. A combination of (a) a compound according to any one of claims 12 to 15, and (b) one or more other anti-tuberculosis agent.
21. A product containing (a) a compound according to any one of claims 12 to 15, and (b) one or more other anti-tuberculosis agent, as a combined preparation for simultaneous, separate or sequential use in the treatment of tuberculosis.
22. A process for the preparation of a compound of formula (IA) as claimed in any one of Claims 12-15 , which process comprises: (i) reaction of a compound of formula (II), ring A q q ring B 10 in which the variables are as defined in Claim 1, with a compound of formula (III), LG -L (III) wherein L is as defined in Claim 1, but wherein L is not hydrogen, halo or linked to O or S, and LG is a suitable leaving group; (ii) reaction of a compound of formula (IV), ring A ring B wherein the variables are as defined in Claim 1, such as a carboxylic acid ester derivative, with a compound of formula (V) wherein the variables are as hereinbefore defined, under amide coupling reaction conditions; (iii) coupling of a compound of formula (VI), ring A ring B wherein the variables are as defined in Claim 1, and LG represents a suitable leaving group, with a compound of formula (VII), (VII) wherein the variables are as defined in Claim 1; or 10 (iv) coupling of a compound of formula (VIII), (VIII) ring A q q ring B wherein the variables are as defined in Claim 1, and LG represents a suitable leaving group as described above with respect to LG , and may particularly represent chloro, bromo or iodo, with a compound of formula (IX), 5 LG -L (IX) wherein L is as defined in Claim 1, but wherein L is not hydrogen, halo or linked to O or S, and LG is a suitable group.
23. The use as claimed in Claim 1, substantially as herein described with reference to any one of the examples thereof. 10
24. The compound as claimed in any one of Claims 12, 13 or 15, substantially as herein described with reference to any one of the examples thereof.
25. The process as claimed in Claim 22, substantially as herein described with reference to any one of the examples thereof.
NZ737408A 2016-07-01 Antibacterial compounds NZ737408B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
NZ774761A NZ774761B2 (en) 2016-07-01 Antibacterial compounds

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP15174936 2015-07-02
EP16174718 2016-06-16
EP16174713 2016-06-16
PCT/EP2016/065499 WO2017001660A1 (en) 2015-07-02 2016-07-01 Antibacterial compounds

Publications (2)

Publication Number Publication Date
NZ737408A NZ737408A (en) 2024-07-26
NZ737408B2 true NZ737408B2 (en) 2024-10-30

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