Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P27/00—Drugs for disorders of the senses
• • 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
• • 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
  • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
• • 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
  • C07D471/10—Spiro-condensed systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
  • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
  • C07D491/10—Spiro-condensed systems
  • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring

Definitions

• the present invention belongs to the field of medicine, and relates to 2-substituted piperidine derivatives, preparation methods thereof, pharmaceutical compositions comprising the compounds, and medical uses thereof.
• C3 convertases split C3 into C3a and C3b.
• C3b forms additional AP C3 convertases (amplification) as well as C5 convertases.
• C5 convertases cleave C5 into C5a and C5b.
• the produced C5b initiates the formation of the C5b-9 membrane attack complex (MAC) with C6-C9, leading to lysis of bacteria and cells by insertion into a membrane.
• the split products C3a and C5a function as anaphylatoxins to promote pro-inflammatory responses through activation and chemotaxis of leukocytes.
• C3b also plays a key role in removing bacteria and cellular waste such as immune complexes and apoptotic cells through promoting phagocytosis by opsonization.
• the down-stream effects of mannan-induced lectin complement pathway activation depend quantitatively on alternative pathway amplification. Mol. Immunol. 47, 373–380. https: //doi. org/10.1016/j. molimm. 2009.09.005 ) .
• the spontaneous activated C3 forms C3 convertase by binding with factor B (FB) .
• C3b and Bb After cleavage of FB into Bb by factor D, C3b and Bb generate the AP C3 convertase (C3bBb) .
• the newly formed C3bBb cleaves more C3 to generate more AP C3 convertases, leading to the amplification of complement cascade.
• This invention aims to provide compounds which modulate Factor B and treat disorders associated with the dysregulation of the Complement pathway.
• the present invention in one aspect, provides a compound of formula (I) , or a tautomer, cis-or trans-isomer, mesomer, racemate, enantiomer, diastereomer, or mixture thereof, or a pharmaceutically acceptable salt, solvate, or prodrug thereof,
• A is cycloalkyl, heterocyclyl, aryl or heteroaryl
• L is bond, (CR a R b ) p ;
• R a and R b are independently selected from the group consisting of hydrogen, deuterium, halogen, amino, cyano, hydroxy, alkyl, alkoxy, alkylthio, haloalkyl, hydroxyalkyl, cycloalkyl, heterocyclyl, aryl and heteroaryl;
• R 5 together with the C atom to which they are attached form a cycloalkyl or heterocyclyl, optionally the cycloalkyl or heterocyclyl substituted with one or more substituents selected from hydrogen, deuterium, halogen, amino, cyano, hydroxy, alkyl, alkoxy, alkylalkoxy, alkoxyalkyl, alkylthio, haloalkyl and hydroxyalkyl;
• n 1, 2 or 3;
• L is bond, CH 2 .
• R 1 and R 2 are independently selected from hydrogen.
• R 3 and R 4 are independently selected from the group consisting of hydrogen, deuterium, halogen, amino, cyano, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 haloalkyl, C 1-6 haloalkenyl C 1-6 hydroxyalkyl, deuterated C 1-6 alkoxy, C 1-6 haloalkoxy, C 3-6 cycloalkyl, 4-10 membered heterocyclyl, C 6-10 aryl, 5-10 membered heteroaryl, C 3-6 cycloalkyloxy, 4-10 membered heterocyclyloxy, C 6-10 aryloxy and 5-10 membered heteroaryloxy, optionally the C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, deuterated C 1-6 alkoxy, C 1-6 haloalkoxy substituted with
• R 3 and R 4 are independently selected from the group consisting of deuterium, halogen, C 1-3 alkyl, C 1-3 alkoxy, deuterated C 1-3 alkoxy, C 1-3 haloalkoxy, C 3-6 cycloalkyl and C 3-6 cycloalkyloxy, optionally the C 1-3 alkyl, C 1-3 alkoxy, deuterated C 1-3 alkoxy, C 1-3 haloalkoxy substituted with one or more substituents selected from C 3-6 cycloalkyl, 4-6 membered heterocyclyl, C 6-10 aryl and 5-10 membered heteroaryl.
• R 5 is independently selected from the group consisting of hydrogen, deuterium, halogen, amino, cyano, hydroxy, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1- 6 alkylthio, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 3-8 cycloalkyl, 4-10 membered heterocyclyl, C 5-10 aryl and 5-10 membered heteroaryl, optionally the C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 3-8 cycloalkyl, 4-10 membered heterocyclyl, C 5-10 aryl and 5-10 membered heteroaryl substituted with one or more substituents selected from deuterium, halogen, amino, cyano, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6
• two of R 5 together with the C atom to which they are attached form C 3-6 cycloalkyl or 4-6 membered heterocyclyl containing 1, 2 or 3 heteroatoms selected from N, O or S, optionally substituted with one or more substituents selected from hydrogen, deuterium, halogen, amino, cyano, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylC 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, C 1-6 alkylthio, C 1-6 haloalkyl and C 1-6 hydroxyalkyl.
• two of R 5 together with the C atom to which they are attached form a carbon-carbon double bond.
• R 6 is selected from the group consisting of hydrogen, deuterium, halogen, amino, cyano, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 3-8 cycloalkyl, 4-10 membered heterocyclyl, C 5-10 aryl and 5-10 membered heteroaryl, – (CH 2 ) r C 1-6 alkoxy, – (CH 2 ) r C (O) OH, -S (O) NHC 1-6 alkyl, -SO 2 C 1-6 alkyl, -C (O) NHSO 2 C 1-6 alkyl and -SO 2 NHC (O) C 1-6 alkyl.
• R 6 is -F, -OMe, -CH 2 OH, -CH 2 OCH 3 , -CH 2 F, -CF 2 H, -CF 3 , –COOH, -C (O) NHSO 2 CH 3 , -S (O) NHCH 3 , or 5-6 membered heterocyclyl containing 1-3 of heteroatom selected from N, O and S, or 5-6 membered heteroaryl containing 1-3 of heteroatom selected from N, O and S.
• R 7 is hydrogen or C 1-3 alkyl.
• R 9 is selected from the group consisting of deuterium, halogen, amino, cyano, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 3-8 cycloalkyl and 4-10 membered heterocyclyl containing 1, 2 or 3 heteroatoms selected from N, O or S.
• R 9 is selected from the group consisting of deuterium, halogen, amino, cyano, hydroxy, C 1-3 alkyl, C 1-6 alkoxy, C 1-3 alkylthio, C 1-3 haloalkyl, C 1-3 hydroxyalkyl, C 3-6 cycloalkyl and 4-6 membered heterocyclyl containing 1, 2 or 3 heteroatoms selected from N, O or S.
• R 9 is selected from the group consisting of deuterium, halogen, amino, cyano, hydroxy, methyl, ethyl, cyclopropyl, cyclobutyl.
• R 9 taken together with one of R 6 form a saturated or unsaturated C 3-7 cycloalkyl or a saturated or unsaturated 3-7 membered heterocyclyl containing 1, 2 or 3 heteroatoms selected from N, O or S, optionally the C 3-7 cycloalkyl or 3-7 membered heterocyclyl is substituted with 1 or 2 substituents selected from hydrogen, deuterium, halogen, amino, cyano, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylalkoxy, C 1-6 alkoxyalkyl, C 1-6 alkylthio, C 1-6 haloalkyl and C 1-6 hydroxyalkyl, and another R 6 is selected from the group consisting of hydrogen, deuterium, halogen, amino, cyano, hydroxy, C 1-3 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 3
• R 9 taken together with one of R 6 form a saturated or unsaturated C 4-6 cycloalkyl or a saturated or unsaturated 4-7 membered heterocyclyl containing 1, 2 or 3 heteroatoms selected from N, O or S, optionally the saturated or unsaturated C 4-6 cycloalkyl or saturated or unsaturated 4-7 membered heterocyclyl is substituted with 1 or 2 substituents selected from hydrogen, deuterium, halogen, amino, cyano, hydroxy, C 1-3 alkyl, C 1-3 alkoxy, C 1-3 alkylalkoxy, C 1-3 alkoxyalkyl, C 1-3 alkylthio, C 1-3 haloalkyl and C 1-3 hydroxyalkyl, and another R 6 is selected from the group consisting of F, -OMe, -CH 2 OH, -CH 2 OCH 3 , -CH 2 F, -CF 2 H, -CF 3 , –COOH, -C (O)
• the compound of formula (I) may be compounds of formula (II) , or a tautomer, cis-or trans-isomer, mesomer, racemate, enantiomer, diastereomer, or mixture thereof, or a pharmaceutically acceptable salt, solvate, or prodrug thereof,
• the compound of formula (I) may be compounds of formula (III-a) - (III-b) , or a tautomer, cis-or trans-isomer, mesomer, racemate, enantiomer, diastereomer, or mixture thereof, or a pharmaceutically acceptable salt, solvate, or prodrug thereof,
• X is CR c R d , NR e , O or S;
• R c, R d and R e are independently selected from the group consisting of hydrogen, deuterium, halogen, amino, cyano, hydroxy, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkylthio, C 1-6 haloalkyl, C 1-6 hydroxyalkyl, C 3-8 cycloalkyl, C 3-8 heterocyclyl, C 6-10 aryl and C 6-10 heteroaryl;
• R c, R d and R e are independently selected from the group consisting of hydrogen, deuterium, halogen, amino, cyano, hydroxy, C 1-3 alkyl, C 1-3 alkoxy, C 1-3 alkylthio, C 1-3 haloalkyl, C 1-3 hydroxyalkyl, C 3-6 cycloalkyl, C 4-6 heterocyclyl, C 6-10 aryl and C 6-10 heteroaryl;
• R c, R d and R e are independently selected from the group consisting of hydrogen, deuterium, halogen, amino, cyano, hydroxy, methyl, ethyl;
• v 0, 1, 2 or 3.
• the compound of formula (I) may be compounds of formula (IV-a) -(IV-f) , or a tautomer, cis-or trans-isomer, mesomer, racemate, enantiomer, diastereomer, or mixture thereof, or a pharmaceutically acceptable salt, solvate, or prodrug thereof,
• R 10 is selected from deuterium, halogen, amino, cyano, hydroxy, C 1-3 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-3 alkoxy, C 1-3 alkylC 1-3 alkoxy, C 1-3 alkoxyC 1-3 alkyl, C 1-3 alkylthio, C 1-3 haloalkyl and C 1-3 hydroxyalkyl;
• n 1;
• z 0, 1, 2 or 3.
• the compound of formula (I) may be compounds of formula (V-a) -(V-b) , or a tautomer, cis-or trans-isomer, mesomer, racemate, enantiomer, diastereomer, or mixture thereof, or a pharmaceutically acceptable salt, solvate, or prodrug thereof,
• the compound, tautomer, cis-or trans-isomer, mesomer, racemate, enantiomer, diastereomer, or mixture thereof, or pharmaceutically acceptable salts thereof is can be administered by any suitable route of administration, e.g. oral, parenteral, buccal, sublingual, nasal, rectal, intrathecal or transdermal administration, and the pharmaceutical compositions adapted accordingly.
• the present invention relates to a method of treating a disorder or a disease in a subject mediated by complement activation, in particular mediated by activation of the complement alternative pathway, comprising administering to a subject in need thereof an effective amount of a compound any formula (I) - (VI-f) , or a pharmaceutical composition comprising the same.
• the disease or disorder is selected from the group consisting of age-related macular degeneration, geographic atrophy, diabetic retinopathy, uveitis, retinitis pigmentosa, macular edema, Behcet's uveitis, multifocal choroiditis, Vogt-Koyangi-Harada syndrome, imtermediate uveitis, birdshot retino-chorioditis, sympathetic ophthalmia, ocular dicatricial pemphigoid, ocular pemphigus, nonartertic ischemic optic neuropathy, post-operative inflammation, retinal vein occlusion, neurological disorders, multiple sclerosis, stroke, Guillain Barre Syndrome, traumatic brain injury, Parkinson's disease, disorders of inappropriate or undesirable complement activation, hemodialysis complications, hyperacute allograft rejection, xenograft rejection, interleukin-2 induced toxicity during IL-2 therapy, inflammatory disorders, inflammation
• the substituent group (s) is preferably one or more, sometimes preferably one to five, sometimes more preferably one to three, group (s) independently selected from the group consisting of selected from alkyl, alkenyl, alkynyl, alkoxy, alkylsulfo, alkylamino, halogen, thiol, hydroxy, nitro, cyano, cycloalkyl, heterocyclic alkyl, aryl, heteroaryl, cycloalkoxyl, heterocylic alkoxyl, cycloalkylthio and heterocylic alkylthio.
• the substituent group (s) is preferably one or more, sometimes preferably one to five, sometimes more preferably one to three, group (s) independently selected from the group consisting of selected from alkyl, alkenyl, alkynyl, alkoxy, alkylsulfo, alkylamino, halogen, thiol, hydroxy, nitro, cyano, cycloalkyl, heterocyclic alkyl, aryl, heteroaryl, cycloalkoxyl, heterocylic alkoxyl, cycloalkylthio and heterocylic alkylthio.
• “Spiro Cycloalkyl” refers to a 5 to 20 membered polycyclic group with rings connected through one common carbon atom (called a spiro atom) , wherein one or more rings can contain one or more double bonds, but none of the rings has a completely conjugated pi-electron system.
• a spiro cycloalkyl is 6 to 14 membered, more preferably 7 to 10 membered, and most preferably . 7 to 8 membered.
• a spiro cycloalkyl is divided into mono-spiro cycloalkyl, di-spiro cycloalkyl, or poly-spiro cycloalkyl, and preferably refers to a mono-spiro cycloalkyl or di-spiro cycloalkyl, more preferably 4-membered/4-membered, 4-membered/5-membered, 4-membered/6-membered, 5-membered/5-membered, or 5-membered/6-membered mono-spiro cycloalkyl.
• Representative examples of spiro cycloalkyl include, but are not limited to the following substituents:
• fused cycloalkyl is divided into bicyclic, tricyclic, tetracyclic or polycyclic fused cycloalkyl, and preferably refers to a bicyclic or tricyclic fused cycloalkyl, more preferably 5-membered/5-membered, or 5-membered/6-membered bicyclic fused cycloalkyl.
• fused cycloalkyls include, but are not limited to, the following substituents:
• Bridged Cycloalkyl refers to a 5 to 20 membered polycyclic hydrocarbon group, wherein every two rings in the system share two disconnected carbon atoms. The rings can have one or more double bonds, but have no completely conjugated pi-electron system.
• a bridged cycloalkyl is 6 to 14 membered, more preferably 7 to 10 membered, and most preferably 7 to 8 membered.
• bridged cycloalkyl is divided into bicyclic, tricyclic, tetracyclic or polycyclic bridged cycloalkyl, and preferably refers to a bicyclic, tricyclic or tetracyclic bridged cycloalkyl, more preferably a bicyclic or tricyclic bridged cycloalkyl.
• Representative examples of bridged cycloalkyls include, but are not limited to, the following substituents:
• the cycloalkyl can be fused to the ring of an aryl, heteroaryl or heterocyclic alkyl, wherein the ring bound to the parent structure is cycloalkyl.
• Representative examples include, but are not limited to indanylacetic, tetrahydronaphthalene, benzocycloheptyl and so on.
• the cycloalkyl is optionally substituted or unsubstituted.
• the substituent group (s) is preferably one or more, sometimes preferably one to five, sometimes more preferably one to three, substituents independently selected from the group consisting of alkyl, halogen, alkoxy, alkenyl, alkynyl, alkylsulfo, alkylamino, thiol, hydroxy, nitro, cyano, amino, cycloalkyl, heterocyclic alkyl, aryl, heteroaryl, cycloalkoxyl, heterocylic, cycloalkylthio, heterocylic alkylthio and oxo group.
• substituents include, but are not limited to, the following substituents:
• Heterocyclyl refers to a 3 to 20 membered saturated and/or partially unsaturated monocyclic or polycyclic hydrocarbon group having one or more, sometimes preferably one to five, sometimes more preferably one to three, heteroatoms selected from the group consisting of N, O, and S (O) m (wherein m is 0, 1, or 2) as ring atoms, but excluding -O-O-, -O-S-or -S-S-in the ring, the remaining ring atoms being C.
• heterocyclyl is a 3 to 12 membered having 1 to 4 heteroatoms; more preferably a 3 to 10 membered having 1 to 3 heteroatoms; most preferably a 5 to 6 membered having 1 to 2 heteroatoms.
• monocyclic heterocyclyls include, but are not limited to, pyrrolidyl, piperidyl, piperazinyl, morpholinyl, sulfo-morpholinyl, homopiperazinyl, and so on.
• Polycyclic heterocyclyl includes the heterocyclyl having a spiro ring, fused ring or bridged ring.
• “Spiro heterocyclyl” refers to a 5 to 20 membered polycyclic heterocyclyl with rings connected through one common carbon atom (called a spiro atom) , wherein said rings have one or more, sometimes preferably one to five, sometimes more preferably one to three, heteroatoms selected from the group consisting of N, O, and S (O) m (wherein m is 0, 1 or 2) as ring atoms, the remaining ring atoms being C, wherein one or more rings can contain one or more double bonds, but none of the rings has a completely conjugated pi-electron system.
• a spiro heterocyclyl is 6 to 14 membered, more preferably 7 to 10 membered, and most preferably 7 to 8 membered.
• spiro heterocyclyl is divided into mono-spiro heterocyclyl, di-spiro heterocyclyl, or poly-spiro heterocyclyl, and preferably refers to mono-spiro heterocyclyl or di-spiro heterocyclyl, more preferably 4-membered/4-membered, 4-membered/5-membered, 4-membered/6-membered, 5-membered/5-membered, or 5-membered/6-membered mono-spiro heterocyclyl.
• Representative examples of spiro heterocyclyl include, but are not limited to the following substituents:
• “Fused Heterocyclyl” refers to a 5 to 20 membered polycyclic heterocyclyl group, wherein each ring in the system shares an adjacent pair of carbon atoms with the other ring, wherein one or more rings can contain one or more double bonds, but none of the rings has a completely conjugated pi-electron system, and wherein said rings have one or more, sometimes preferably one to five, sometimes more preferably one to three, heteroatoms selected from the group consisting of N, O, and S (O) p (wherein p is 0, 1, or 2) as ring atoms, the remaining ring atoms being C.
• bridged heterocyclyl include, but are not limited to, the following substituents:
• hydrogen atmosphere means that a reaction flask was equipped with a balloon having 1 L of hydrogen.
• Factor B binding affinity of each compound tested was determined using a time-resolved fluorescence resonance energy transfer (TR-FRET) techonology. 10 nM recombinant his-tagged Factor B catalytic domain, varying concentrations of inhibitors, 4 nM LANCE Eu-W1024 Anti-6xHis Antibody and 100 nM TRFRET_tool2 tracer was incubated in 1X Kinase Buffer A for 1 h. Measurement was performed in a reaction volume of 15 ⁇ L by adding 5 ⁇ L of the test compound, 5 ⁇ L of Factor B/antibody mixture and 5 ⁇ L of tracer into white opaque 384-well assay plates.
• TR-FRET time-resolved fluorescence resonance energy transfer
• the TR-FRET signal was read on a plate reader with an excitation wavelength of 340 nm and detection wavelengths of 615 and 665 nm. Binding affinity was determined for each compound by measuring TR-FRET signal at various concentrations of compound and plotting the relative fluorescence Emission Ratio (665 nm/615 nm) against the inhibitor concentration to estimate the IC 50 from [Compound] vs Emission Ratio using the four parameters dose-response inhibition curve with a variable slope model in GraphPad Prism.
• Example compounds in present invention were tested in above assay and show IC 50 (nM) 0.5-250 nM against human Factor B.
• Recombinant human Factor B catalytic domain (a. a. 470-764, C-terminal his-tagged, produced in-house)

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