RU2008115512A - ИНГИБИТОРЫ МЕТАЛЛО-β-ЛАКТАМАЗЫ - Google Patents

ИНГИБИТОРЫ МЕТАЛЛО-β-ЛАКТАМАЗЫ Download PDF

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RU2008115512A
RU2008115512A RU2008115512/04A RU2008115512A RU2008115512A RU 2008115512 A RU2008115512 A RU 2008115512A RU 2008115512/04 A RU2008115512/04 A RU 2008115512/04A RU 2008115512 A RU2008115512 A RU 2008115512A RU 2008115512 A RU2008115512 A RU 2008115512A
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alkyl
group
substituted
pharmaceutically acceptable
heterocycle
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RU2008115512/04A
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RU2462450C2 (ru
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Кен ТИКАУТИ (JP)
Кен ТИКАУТИ
Мизуйо ИДА (JP)
Мизуйо ИДА
Такао АБЕ (JP)
Такао АБЕ
Юкико ХИРАЙВА (JP)
Юкико ХИРАЙВА
Акихиро МОРИНАКА (JP)
Акихиро МОРИНАКА
Тосиаки КУДО (JP)
Тосиаки КУДО
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Мейдзи Сейка Кайся, Лтд. (Jp)
Мейдзи Сейка Кайся, Лтд.
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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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/225—Polycarboxylic acids
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/194—Carboxylic acids, e.g. valproic acid having two or more carboxyl groups, e.g. succinic, maleic or phthalic acid
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    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
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    • A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
    • A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
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    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
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    • A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
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    • 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
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
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    • 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
    • A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
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    • 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
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    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
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    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
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    • C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms
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    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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Abstract

1. Ингибитор металло-β-лактамазы, который включает соединение, представленное следующей формулой (I), или его соль или сольват: ! ! R1 обозначает C2-6-алкил, C3-7-циклоалкил, гидроксиметил, -C1-3-алкиленфенил, -C0-1-алкиленгетероцикл, -O-C1-6-алкил или -S-C1-6-алкил, которые могут быть замещены, ! R2 обозначает C1-6-алкил, C3-7-циклоалкил, гидроксиметил групп, -C1-3-алкиленфенил, -C0-1-алкиленгетероцикл, -O-C1-6-алкил или -S-C1-6-алкил, которые могут быть замещены, ! каждый M1 независимо обозначает атом водорода, фармацевтически приемлемый катион или фармацевтически приемлемую группу, которая может быть гидролизована in vivo. ! 2. Ингибитор металло-β-лактамазы по п.1, в котором ! R1 обозначает C2-6-алкил, С3-7-циклоалкил, гидроксиметил, бензил, фенетил, -C0-1-алкилен-гетероцикл, причем гетероцикл представляет собой тетрагидропиран, пиридин или пиперидин, -O-C1-6-алкил или -S-С1-6-алкил, которые могут быть замещены, ! R2 обозначает С1-6-алкил, С3-7-циклоалкил, гидроксиметил, бензил, фенетил, -C0-1-алкилен-гетероцикл, причем гетероцикл представляет собой тетрагидропиран, пиридин или пиперидин, -O-C1-6-алкил или -S-С1-6-алкил, которые могут быть замещены, ! оба M1, которые могут быть одинаковыми или разными, обозначают атом водорода, фармацевтически приемлемый катион или фармацевтически приемлемую группу, которая может быть гидролизована in vivo. ! 3. Ингибитор металло-β-лактамазы по п.1, в котором ! R1 обозначает C2-6-алкил, С3-7-циклоалкил, который может быть замещен гидроксильной группой и может быть конденсирован с арилом; гидроксиметил, -С1-3-алкиленфенил, причем указанная фенильная группа может быть замещена гидроксильной группой, С1-6-алкильной группой, гидроксиметильной группой, группой -COOM, гд�

Claims (21)

1. Ингибитор металло-β-лактамазы, который включает соединение, представленное следующей формулой (I), или его соль или сольват:
Figure 00000001
R1 обозначает C2-6-алкил, C3-7-циклоалкил, гидроксиметил, -C1-3-алкиленфенил, -C0-1-алкиленгетероцикл, -O-C1-6-алкил или -S-C1-6-алкил, которые могут быть замещены,
R2 обозначает C1-6-алкил, C3-7-циклоалкил, гидроксиметил групп, -C1-3-алкиленфенил, -C0-1-алкиленгетероцикл, -O-C1-6-алкил или -S-C1-6-алкил, которые могут быть замещены,
каждый M1 независимо обозначает атом водорода, фармацевтически приемлемый катион или фармацевтически приемлемую группу, которая может быть гидролизована in vivo.
2. Ингибитор металло-β-лактамазы по п.1, в котором
R1 обозначает C2-6-алкил, С3-7-циклоалкил, гидроксиметил, бензил, фенетил, -C0-1-алкилен-гетероцикл, причем гетероцикл представляет собой тетрагидропиран, пиридин или пиперидин, -O-C1-6-алкил или -S-С1-6-алкил, которые могут быть замещены,
R2 обозначает С1-6-алкил, С3-7-циклоалкил, гидроксиметил, бензил, фенетил, -C0-1-алкилен-гетероцикл, причем гетероцикл представляет собой тетрагидропиран, пиридин или пиперидин, -O-C1-6-алкил или -S-С1-6-алкил, которые могут быть замещены,
оба M1, которые могут быть одинаковыми или разными, обозначают атом водорода, фармацевтически приемлемый катион или фармацевтически приемлемую группу, которая может быть гидролизована in vivo.
3. Ингибитор металло-β-лактамазы по п.1, в котором
R1 обозначает C2-6-алкил, С3-7-циклоалкил, который может быть замещен гидроксильной группой и может быть конденсирован с арилом; гидроксиметил, -С1-3-алкиленфенил, причем указанная фенильная группа может быть замещена гидроксильной группой, С1-6-алкильной группой, гидроксиметильной группой, группой -COOM, где М обозначает атом водорода или фармацевтически приемлемый катион, группой -СО-NR22R23, где R22 и R23, которые могут быть одинаковыми или разными, обозначает атом водорода или С1-6-алкил, где указанный алкил может быть дополнительно замещен аминокарбонильной группой, или R22 и R23, вместе с атомом азота, с которым связаны R22 и R23, могут образовывать пяти- или шестичленное насыщенное гетероциклическое кольцо, содержащее 1-2 атома кислорода или азота, предпочтительно, морфонил, пиперазил или пиперидил, и гетероцикл может быть замещен гидроксильной группой или С1-6-алканоилоксигруппой, группой -O-R24, где R24 обозначает С1-6-алкил, причем алкил обозначает -COOM, где М обозначает атом водорода, С1-6-алкил или фармацевтически приемлемый катион, аминокарбонил, аминогруппу, гуанидиногруппу или пяти- или шестичленный ненасыщенный гетероцикл, имеющий 1-2 атома азота, или пяти- или шестичленный насыщенный гетероцикл, имеющий 1-2 атома азота, предпочтительно пирролидин, -C0-1-алкиленгетероцикл, где указанный гетероцикл представляет собой пяти- или шестичленный насыщенный или ненасыщенный гетероцикл, содержащий один атом азота или кислорода и может быть замещен гидроксильной группой, -O-С1-6-алкил, или -S-С1-6-алкил, и R2 обозначает С1-6-алкил, С3-7-циклоалкил, где указанный цикл может быть замещен гидроксильной группой или может быть конденсирован с арилом, гидроксиметил, -С1-3-алкиленфенил, -C1-3-алкиленфенил, где указанная фенильная группа может быть замещена гидроксильной группой, С1-6-алкильной группой, гидроксиметильной группой, группой -COOM, где М обозначает атом водорода или фармацевтически приемлемый катион, группой -СО-NR22R23, где R22 и R23, которые могут быть одинаковыми или разными, обозначает атом водорода или С1-6-алкил, где указанный алкил может быть дополнительно замещен аминокарбонильной группой, или R22 и R23, вместе с атомом азота, с которым связаны R22 и R23, могут образовывать пяти- или шестичленное насыщенное гетероциклическое кольцо, содержащее 1-2 атома кислорода или азота, предпочтительно, морфонил, пиперазил или пиперидил, и гетероцикл может быть замещен гидроксильной группой или С1-6-алканоилоксигруппой, группой -O-R24, где R24 обозначает С1-6-алкил, причем алкил обозначает -COOM, где М обозначает атом водорода, С1-6-алкил или фармацевтически приемлемый катион, аминокарбонил, аминогруппу, гуанидиногруппу или пяти- или шестичленный ненасыщенный гетероцикл, имеющий 1-2 атома азота, или пяти- или шестичленный насыщенный гетероцикл, имеющий 1-2 атома азота, предпочтительно пирролидин, -C0-1-алкиленгетероцикл, где указанный гетероцикл представляет собой пяти- или шестичленный насыщенный или ненасыщенный гетероцикл, содержащий один атом азота или кислорода и может быть замещен гидроксильной группой -O-С1-6-алкил, или -S-С1-6-алкил.
4. Ингибитор металло-β-лактамазы по п.1, в котором R1 обозначает C2-6-алкил; С3-7-циклоалкил, где указанный цикл может быть замещен гидроксильной группой или может быть конденсирован с арилом; гидроксиметил; -C1-3-алкиленфенил, где указанная фенильная группа может быть замещена гидроксильной группой, С1-6-алкильной группой, гидроксиметильной группой, группой -COOM, где М обозначает атом водорода или фармацевтически приемлемый катион, группой -СО-NR22R23, где R22 и R23, которые могут быть одинаковыми или разными, обозначает атом водорода или С1-6-алкил, предпочтительно, С1-4-алкил, более предпочтительно, С1-2-алкил, причем алкил может быть дополнительно замещен аминокарбонилом, или R22 и R23, вместе с атомом азота, с которым связаны
R22 и R23, могут образовывать пяти- или шестичленное насыщенное гетероциклическое кольцо, содержащее 1-2 атома кислорода или азота, предпочтительно, морфонил, пиперазил или пиперидил, и гетероцикл может быть замещен гидроксильной группой или С1-6-алканоилоксигруппой, группой -O-R24, где R24 обозначает С1-6-алкил, причем алкил обозначает -COOM, где М обозначает атом водорода, С1-6-алкил или фармацевтически приемлемый катион, аминокарбонил, аминогруппу, гуанидиногруппу или пяти- или шестичленный ненасыщенный гетероцикл, имеющий 1-2 атома азота, или пяти- или шестичленный насыщенный гетероцикл, имеющий 1-2 атома азота, -C0-1-алкиленгетероцикл, где указанный гетероцикл представляет собой пяти- или шестичленный насыщенный или ненасыщенный гетероцикл, содержащий один атом азота или кислорода и может быть замещен гидроксильной группой; -O-С1-6-алкил; или -S-С1-6-алкил.
5. Ингибитор металло-β-лактамазы по п.1, в котором R1 и R2 обозначают C2-4-алкил.
6. Фармацевтическая композиция, содержащая соединение, представленное общей формулой (I), определенной в п.1, и фармацевтически приемлемый носитель.
7. Фармацевтическая композиция по п.6, используемая в качестве ингибитора металло-β-лактамазы.
8. Фармацевтическая композиция по п.6, которую вводят совместно или последовательно с β-лактамовым антибиотиком.
9. Фармацевтическая композиция по п.8, которую вводят совместно или последовательно с дегидропептидазой и/или ингибиторами β-лактамазы, отличными от соединения общей формулы (I).
10. Фармацевтическая композиция по п.6, в которой указанным β-лактамовым антибиотиком является карбапенемовый антибиотик.
11. Фармацевтическая композиция, содержащая ингибитор металло-β-лактамазы, определенный в п.1, β-лактамовый антибиотик и, в случае необходимости, фармацевтически приемлемый носитель.
12. Фармацевтическая композиция по любому из пп.6-11, используемая в качестве антибиотика.
13. Способ лечения бактериальных инфекций, который включает совместное введение β-лактамового антибиотика и ингибитора металло-β-лактамазы, определенного в п.1.
14. Способ по п.13, в котором указанным β-лактамовым антибиотиком является карбапенемовый антибиотик.
15. Соединение, представленное следующей общей формулой (II), или его соль или сольват:
Figure 00000002
в которой
R3 обозначает C2-6-алкил, C3-7-циклоалкил или гидроксиметил, которые могут быть замещены,
R4 обозначает C1-6-алкил или C3-7-циклоалкил, которые могут быть замещены,
каждый M2 независимо обозначает атом водорода, фармацевтически приемлемый катион или фармацевтически приемлемую группу, которая может быть гидролизована in vivo.
16. Соединение, представленное следующей общей формулой (III), или его соль или сольват:
Figure 00000003
в которой
R5 обозначает этил,
R6 обозначает прямой C1-3-алкил, обе группы M3, которые могут быть одинаковыми или разными, обозначают фармацевтически приемлемый катион или фармацевтически приемлемую группу, которая может быть гидролизована in vivo.
17. Соединение, представленное следующей общей формулой (IV), или его соль или сольват:
Figure 00000004
в которой
R7 обозначает C1-6-алкил, C3-7-циклоалкил, -C1-3-алкиленфенил, -C1-алкилен-кольцо A, -O-C1-6-алкил или -S-C1-6-алкил, которые могут быть замещены,
R8 обозначает -C1-3-алкиленфенил, -C0-1-алкилен-кольцо A, -O-C1-6-алкил или -S-C1-6-алкил, которые могут быть замещены,
кольцо A обозначает пяти-десятичленное моно- или бициклическое гетероциклическое кольцо, содержащее 1-4 гетероатома, выбранных из атомов азота, кислорода и серы,
каждый M4 независимо обозначает атом водорода, фармацевтически приемлемый катион или фармацевтически приемлемую группу, которая может быть гидролизована in vivo, при условии, что, когда R7 обозначает C1-6-алкил, R8 исключает дигидрофуран.
18. Соединение по п.17, в котором кольцо A представляет собой тетрагидрофуран, фуран, пирролидин, пиперидин, пиразолидин, имидазолидин, пиперазин, морфолин, тиоморфолин, пиррол, тиофен, оксазол, изоксазол, тиазол, изотиазол, имидазол, пиразол, пиридин, пиридазин, пиримидин, пиразин, триазол, тетразол, тиадиазол, азетидин, тиазолин, хинуклидин, триазин, изобензофуран, индол, индолизин, хромен, хинолин, изохинолин, циннолин, хиназолин, хиноксалин, фталазин, пурин, птеридин или их соль или сольват.
19. Соединение, представленное следующей общей формулой (IV), или его соль или сольват:
Figure 00000005
в которой
R9 обозначает C1-6-алкил, C3-7-циклоалкил, -C1-3-алкиленфенил, -C0-1-алкилен-кольцо B, -O-C1-6-алкил или -S-C1-6-алкил, которые могут быть замещены,
R10 обозначает -C1-3-алкиленфенил, -C0-1-алкилен-кольцо B, -O-C1-6-алкил или
-S-C1-6-алкил, которые могут быть замещены,
кольцо B обозначает пиридин, пиперидин или тетрагидропиран,
каждый M5 независимо обозначает атом водорода, фармацевтически приемлемый катион или фармацевтически приемлемую группу, которая может быть гидролизована in vivo, при условии, что случай, когда R9 и R10 обозначают пиридиний, исключен.
20. Соединение по любому из пп.15-19, где указанный фармацевтически приемлемый катион представляет собой катион металла или катион аммония.
21. Применение соединения, определенного в любом из пп.1-5 и 15-20, для профилактики или лечения бактериальных инфекций.
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BRPI0616137A2 (pt) 2005-09-22 2011-06-07 Meiji Seika Kaisha inibidor da metalo-ß-lactamase, composição farmacêutica, processo para tratar infecções bacterianas, composto, e, uso do mesmo

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EP1941873A4 (en) 2012-09-26
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JP2013032361A (ja) 2013-02-14
CA2620675A1 (en) 2007-03-29
CN102964239A (zh) 2013-03-13
BRPI0616137A2 (pt) 2011-06-07
JP4122049B2 (ja) 2008-07-23
CN101267815A (zh) 2008-09-17
US8093294B2 (en) 2012-01-10
WO2007034924A1 (ja) 2007-03-29
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US9260375B2 (en) 2016-02-16
EP1941873A1 (en) 2008-07-09
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