EA028076B1 - Насыщенные азотсодержащие и n-ацилированные гетероциклы, усиливающие действие активного антибиотика против микобактерий - Google Patents
Насыщенные азотсодержащие и n-ацилированные гетероциклы, усиливающие действие активного антибиотика против микобактерий Download PDFInfo
- Publication number
- EA028076B1 EA028076B1 EA201590828A EA201590828A EA028076B1 EA 028076 B1 EA028076 B1 EA 028076B1 EA 201590828 A EA201590828 A EA 201590828A EA 201590828 A EA201590828 A EA 201590828A EA 028076 B1 EA028076 B1 EA 028076B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- compound according
- antibiotic
- substituted
- phenyl substituted
- phenyl
- Prior art date
Links
- 230000003115 biocidal effect Effects 0.000 title claims abstract description 29
- 230000000694 effects Effects 0.000 title claims abstract description 22
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 5
- 230000003389 potentiating effect Effects 0.000 title abstract 2
- 150000002829 nitrogen Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 37
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 35
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 21
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 201000008827 tuberculosis Diseases 0.000 claims abstract description 13
- 241000894006 Bacteria Species 0.000 claims abstract description 11
- 206010062207 Mycobacterial infection Diseases 0.000 claims abstract description 11
- 208000027531 mycobacterial infectious disease Diseases 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 9
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 8
- 230000001580 bacterial effect Effects 0.000 claims abstract description 8
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 239000011737 fluorine Substances 0.000 claims abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 3
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 30
- 229960002001 ethionamide Drugs 0.000 claims description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 206010024229 Leprosy Diseases 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 230000037361 pathway Effects 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 206010003754 Atypical mycobacterial infections Diseases 0.000 claims description 8
- VRDIULHPQTYCLN-UHFFFAOYSA-N Prothionamide Chemical compound CCCC1=CC(C(N)=S)=CC=N1 VRDIULHPQTYCLN-UHFFFAOYSA-N 0.000 claims description 8
- 229960000918 protionamide Drugs 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 43
- 239000013256 coordination polymer Substances 0.000 description 16
- 229940088710 antibiotic agent Drugs 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- -1 for example Chemical class 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000002708 enhancing effect Effects 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UTBULQCHEUWJNV-UHFFFAOYSA-N 4-phenylpiperidine Chemical compound C1CNCCC1C1=CC=CC=C1 UTBULQCHEUWJNV-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- 239000012047 saturated solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 150000003556 thioamides Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 102100030817 Liver carboxylesterase 1 Human genes 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 101710169844 Sesquipedalian-1 Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 230000008520 organization Effects 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- ABGXADJDTPFFSZ-UHFFFAOYSA-N 4-benzylpiperidine Chemical compound C=1C=CC=CC=1CC1CCNCC1 ABGXADJDTPFFSZ-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 102100025169 Max-binding protein MNT Human genes 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 101100178269 Schizosaccharomyces pombe (strain 972 / ATCC 24843) hob1 gene Proteins 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- JQXXHWHPUNPDRT-YOPQJBRCSA-N chembl1332716 Chemical compound O([C@](C1=O)(C)O\C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)/C=C\C=C(C)/C(=O)NC=2C(O)=C3C(O)=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CCN(C)CC1 JQXXHWHPUNPDRT-YOPQJBRCSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- 230000006872 improvement Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229960003350 isoniazid Drugs 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
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- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
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- 150000003235 pyrrolidines Chemical class 0.000 description 1
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- BWBONKHPVHMQHE-UHFFFAOYSA-N tiocarlide Chemical group C1=CC(OCCC(C)C)=CC=C1NC(=S)NC1=CC=C(OCCC(C)C)C=C1 BWBONKHPVHMQHE-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/451—Non condensed piperidines, e.g. piperocaine having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- 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
-
- 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
-
- 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
- A61P31/08—Antibacterial agents for leprosy
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| FR1203548A FR3000065A1 (fr) | 2012-12-21 | 2012-12-21 | Composes bicycliques ayant une activite potentialisatrice de l'activite d'un antibiotique actif contre les mycobacteries-composition et produit pharmaceutiques comprenant de tels composes |
| PCT/EP2013/077732 WO2014096378A1 (fr) | 2012-12-21 | 2013-12-20 | Hétérocycles azotés saturés et n-acylés potentialisant l'activité d'un antibiotique actif contre les mycobactéries |
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|---|---|
| EA201590828A1 EA201590828A1 (ru) | 2015-11-30 |
| EA028076B1 true EA028076B1 (ru) | 2017-10-31 |
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| IL (1) | IL239504B (enExample) |
| MA (1) | MA38275B1 (enExample) |
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| PE (1) | PE20151327A1 (enExample) |
| PH (1) | PH12015501427B1 (enExample) |
| SG (1) | SG11201504492UA (enExample) |
| TN (1) | TN2015000202A1 (enExample) |
| UA (1) | UA117922C2 (enExample) |
| WO (1) | WO2014096378A1 (enExample) |
| ZA (1) | ZA201503719B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2767542C1 (ru) * | 2021-05-24 | 2022-03-17 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | Противотуберкулезное средство на основе 4-((гет)ароил)-3- гидрокси-1-(2-гидроксифенил)-5-(фенилтио)-1,5-дигидро-2Н-пиррол-2-онов |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA111305C2 (uk) | 2012-12-21 | 2016-04-11 | Пфайзер Інк. | Конденсовані лактами арилу та гетероарилу |
| FR3000064A1 (fr) | 2012-12-21 | 2014-06-27 | Univ Lille Ii Droit & Sante | Composes de type spiroisoxazoline ayant une activite potentialisatrice de l'activite d'un antibiotique-composition et produit pharmaceutiques comprenant de tels composes |
| ES2865402T3 (es) | 2012-12-21 | 2021-10-15 | Janssen Biopharma Inc | 4'-fluoronucleósidos, 4'-fluoronucleótidos y análogos de los mismos para el tratamiento del VHC |
| EP3157915B1 (en) | 2014-06-17 | 2019-02-27 | Pfizer Inc | Substituted dihydroisoquinolinone compounds |
| EP3668853B1 (en) * | 2017-08-16 | 2021-09-29 | GlaxoSmithKline Intellectual Property Development Limited | Novel compounds |
| JP2020531577A (ja) | 2017-08-16 | 2020-11-05 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | 新規化合物 |
| EP3668879B1 (en) * | 2017-08-16 | 2021-09-29 | GlaxoSmithKline Intellectual Property Development Limited | Novel compounds |
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| WO2008003861A1 (fr) * | 2006-07-04 | 2008-01-10 | Institut Pasteur De Lille | Composes a effet potentialisateur de l'activite de l'ethionamide et leurs applications |
| WO2010005783A1 (en) * | 2008-07-08 | 2010-01-14 | Boehringer Ingelheim International Gmbh | Pyrrolidinyl and piperidinyl compounds useful as nhe-1 inhibitors |
| WO2010044885A2 (en) * | 2008-10-17 | 2010-04-22 | Whitehead Institute For Biomedical Research | Soluble mtor complexes and modulators thereof |
| WO2010063774A1 (en) * | 2008-12-02 | 2010-06-10 | Galderma Research & Development | Novel 4-(azacycloalkyl)benzene-1,3-diol compounds as tyrosinase inhibitors, process for the preparation thereof and use thereof in human medicine and in cosmetics |
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| US4093726A (en) | 1976-12-02 | 1978-06-06 | Abbott Laboratories | N-(2-benzimidazolyl)-piperazines |
| US4547505A (en) * | 1983-03-25 | 1985-10-15 | Degussa Aktiengesellschaft | N-Phenyl-N-'-cycloalkylalkanoylpiperazine useful as analgetics and process for its production |
| EP1118612A1 (en) * | 2000-01-21 | 2001-07-25 | Universita Degli Studi di Firenze | Piperazine derivatives possesing nootropic activity |
| TW593556B (en) | 2002-12-27 | 2004-06-21 | Ind Tech Res Inst | Dichroic dye, composition thereof, and liquid crystal composition and liquid-crystal display element containing the same |
| US7601844B2 (en) * | 2006-01-27 | 2009-10-13 | Bristol-Myers Squibb Company | Piperidinyl derivatives as modulators of chemokine receptor activity |
| TW200938203A (en) * | 2007-12-17 | 2009-09-16 | Intervet Int Bv | Anthelmintic agents and their use |
| WO2009080432A2 (en) | 2007-12-21 | 2009-07-02 | Eth Zurich | Composition for treatment of tuberculosis |
| CN102458393B (zh) | 2009-06-25 | 2014-08-20 | 生物验证系统股份公司 | 治疗肺结核的组合物 |
| KR101179508B1 (ko) * | 2010-06-24 | 2012-09-07 | 한국과학기술연구원 | 1,6-이치환-3-아미노-4,5,6,7-테트라하이드로-1Ｈ-피라졸로［3,4-ｃ］피리딘-7-온 화합물 및 이 화합물의 제조방법 |
| US8962658B2 (en) | 2011-10-25 | 2015-02-24 | Universite De Droit Et De La Sante De Lille 2 | Fluoralkylcarbonyl-oxadiazoles |
| CA2873075A1 (en) * | 2012-05-11 | 2013-07-14 | Abbvie Inc. | Nampt inhibitors |
| AU2013292046C1 (en) * | 2012-07-20 | 2018-03-15 | Bayer Pharma Aktiengesellschaft | Novel 5-aminotetrahydroquinoline-2-carboxylic acids and use thereof |
| FR3000064A1 (fr) | 2012-12-21 | 2014-06-27 | Univ Lille Ii Droit & Sante | Composes de type spiroisoxazoline ayant une activite potentialisatrice de l'activite d'un antibiotique-composition et produit pharmaceutiques comprenant de tels composes |
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- 2013-12-20 WO PCT/EP2013/077732 patent/WO2014096378A1/fr not_active Ceased
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- 2013-12-20 BR BR112015014279A patent/BR112015014279A2/pt not_active Application Discontinuation
- 2013-12-20 CN CN201380067137.2A patent/CN104955804B/zh active Active
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| WO2010005783A1 (en) * | 2008-07-08 | 2010-01-14 | Boehringer Ingelheim International Gmbh | Pyrrolidinyl and piperidinyl compounds useful as nhe-1 inhibitors |
| WO2010044885A2 (en) * | 2008-10-17 | 2010-04-22 | Whitehead Institute For Biomedical Research | Soluble mtor complexes and modulators thereof |
| WO2010063774A1 (en) * | 2008-12-02 | 2010-06-10 | Galderma Research & Development | Novel 4-(azacycloalkyl)benzene-1,3-diol compounds as tyrosinase inhibitors, process for the preparation thereof and use thereof in human medicine and in cosmetics |
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| IRIKURA T, ET AL.: "NEW ANALGETIC AGENTS. V.1 1-BUTYRYL-4-EINNAMYLPIPERAZINE HYDROCHLORIDE AND RELATED COMPOUNDS", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 11, no. 04, 1 July 1968 (1968-07-01), pages 801 - 804, XP002930057, ISSN: 0022-2623, DOI: 10.1021/jm00310a022 * |
| MARION FLIPO, MATTHIEU DESROSES, NATHALIE LECAT-GUILLET, BAPTISTE VILLEMAGNE, NICOLAS BLONDIAUX, FLORENCE LEROUX, CATHERINE PIVETE: "Ethionamide Boosters. 2. Combining Bioisosteric Replacement and Structure-Based Drug Design To Solve Pharmacokinetic Issues in a Series of Potent 1,2,4-Oxadiazole EthR Inhibitors", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 55, no. 1, 12 January 2012 (2012-01-12), pages 68 - 83, XP055068481, ISSN: 00222623, DOI: 10.1021/jm200825u * |
| MARION FLIPO, MATTHIEU DESROSES, NATHALIE LECAT-GUILLET, BERTRAND DIRIÉ, XAVIER CARETTE, FLORENCE LEROUX, CATHERINE PIVETEAU, FAT: "Ethionamide Boosters: Synthesis, Biological Activity, and Structure−Activity Relationships of a Series of 1,2,4-Oxadiazole EthR Inhibitors", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 54, no. 8, 28 April 2011 (2011-04-28), pages 2994 - 3010, XP055019892, ISSN: 00222623, DOI: 10.1021/jm200076a * |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2767542C1 (ru) * | 2021-05-24 | 2022-03-17 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | Противотуберкулезное средство на основе 4-((гет)ароил)-3- гидрокси-1-(2-гидроксифенил)-5-(фенилтио)-1,5-дигидро-2Н-пиррол-2-онов |
Also Published As
| Publication number | Publication date |
|---|---|
| SG11201504492UA (en) | 2015-07-30 |
| PH12015501427A1 (en) | 2015-09-14 |
| US9957249B2 (en) | 2018-05-01 |
| AU2013366503A1 (en) | 2015-07-09 |
| TN2015000202A1 (en) | 2016-10-03 |
| FR3000065A1 (fr) | 2014-06-27 |
| MA38275A1 (fr) | 2017-11-30 |
| IL239504B (en) | 2018-10-31 |
| CR20150319A (es) | 2015-09-14 |
| CL2015001640A1 (es) | 2016-01-29 |
| UA117922C2 (uk) | 2018-10-25 |
| PH12015501427B1 (en) | 2015-09-14 |
| WO2014096378A1 (fr) | 2014-06-26 |
| MA38275B1 (fr) | 2018-09-28 |
| IL239504A0 (en) | 2015-08-31 |
| ZA201503719B (en) | 2016-11-30 |
| CA2895606A1 (fr) | 2014-06-26 |
| JP2016503778A (ja) | 2016-02-08 |
| AU2013366503B2 (en) | 2018-02-01 |
| HK1215254A1 (zh) | 2016-08-19 |
| JP6515035B2 (ja) | 2019-05-15 |
| EA201590828A1 (ru) | 2015-11-30 |
| EP2935212A1 (fr) | 2015-10-28 |
| MX2015008029A (es) | 2015-10-30 |
| KR20150138152A (ko) | 2015-12-09 |
| US20150307471A1 (en) | 2015-10-29 |
| GEP20186857B (en) | 2018-06-11 |
| PE20151327A1 (es) | 2015-10-12 |
| BR112015014279A2 (pt) | 2017-07-11 |
| CN104955804B (zh) | 2018-02-09 |
| EP2935212B1 (fr) | 2019-02-27 |
| CN104955804A (zh) | 2015-09-30 |
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