RU2008126228A - 2-аминобензамидное производное - Google Patents
2-аминобензамидное производное Download PDFInfo
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- RU2008126228A RU2008126228A RU2008126228/04A RU2008126228A RU2008126228A RU 2008126228 A RU2008126228 A RU 2008126228A RU 2008126228/04 A RU2008126228/04 A RU 2008126228/04A RU 2008126228 A RU2008126228 A RU 2008126228A RU 2008126228 A RU2008126228 A RU 2008126228A
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- lower alkyl
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- 0 CC(CCC=C(*)C(C)=*1)C(C(NC2(C)/C=C/C3=C/C=C/C=C/C=C3\C(C)(*)/C=C2)=O)=C1N* Chemical compound CC(CCC=C(*)C(C)=*1)C(C(NC2(C)/C=C/C3=C/C=C/C=C/C=C3\C(C)(*)/C=C2)=O)=C1N* 0.000 description 1
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- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- 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
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- 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
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- A—HUMAN NECESSITIES
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- 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
- A61K31/428—Thiazoles condensed with carbocyclic rings
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- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a six-membered aromatic ring
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- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/18—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving halogen atoms of halogenated compounds
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- 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
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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- 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
- C07D207/10—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
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Abstract
1. Ингибитор активации VR1, который включает 2-аминобензамидное производное общей формулы (I) или его соль в качестве активного ингредиента ! ! где - бензольное кольцо или пиридиновое кольцо, ! R3 - одинаковые или отличные друг от друга и каждый представляет собой H, галоген, галоген-низший алкил, циано, нитро, низший алкил, -NR4R5, -низший алкилен-NR4R5, -низший алкилен-NR6-CO2-низший алкил, -O-низший алкил, -O-галоген-низший алкил, фенил или тиенил, ! m - 1, 2 или 3, ! R4 и R5 - одинаковые или отличные друг от друга и каждый представляет собой H или низший алкил, где R4 и R5 могут быть объединены со смежным атомом азота с образованием моноциклического азотсодержащего насыщенного гетерокольца, которое может быть замещено низшим алкилом или группой низший алкилен-OH, ! R6 - H или низший алкил, !- моноциклическое гетерокольцо, циклоалкен или бензольное кольцо, ! где кольцо, представленное как А, может быть замещено 1-4 группами, выбранными из групп -OH, -низший алкилен-OH, -низший алкилен-NR4R5, -низший алкилен-CO-NR4R5, галоген, галоген-низший алкил, низший алкил и оксо, ! R1 - низший алкил, -L-циклоалкил, L-циклоалкенил, -L-моноциклическое кислородсодержащее насыщенное гетерокольцо, -L-моноциклическое азотсодержащее насыщенное гетерокольцо, -L- азотсодержащее насыщенное гетерокольцо, содержащее мостиковую связь, -L-фенил или -L-пиридил, при условии, что тип кольца A, когда R1 представляет собой низший алкил, подразумевает кольцо, которое образует индолин, тетрагидрохинолин или 3,4-дигидро-2H-1,4-бензоксазин вместе с бензольным кольцом, с которым оно конденсировано, ! где низший алкил в группе R1 может быть замещен 1-3 группами, выбранными из групп, представленных в описанной ниже гр�
Claims (15)
1. Ингибитор активации VR1, который включает 2-аминобензамидное производное общей формулы (I) или его соль в качестве активного ингредиента
R3 - одинаковые или отличные друг от друга и каждый представляет собой H, галоген, галоген-низший алкил, циано, нитро, низший алкил, -NR4R5, -низший алкилен-NR4R5, -низший алкилен-NR6-CO2-низший алкил, -O-низший алкил, -O-галоген-низший алкил, фенил или тиенил,
m - 1, 2 или 3,
R4 и R5 - одинаковые или отличные друг от друга и каждый представляет собой H или низший алкил, где R4 и R5 могут быть объединены со смежным атомом азота с образованием моноциклического азотсодержащего насыщенного гетерокольца, которое может быть замещено низшим алкилом или группой низший алкилен-OH,
R6 - H или низший алкил,
где кольцо, представленное как А, может быть замещено 1-4 группами, выбранными из групп -OH, -низший алкилен-OH, -низший алкилен-NR4R5, -низший алкилен-CO-NR4R5, галоген, галоген-низший алкил, низший алкил и оксо,
R1 - низший алкил, -L-циклоалкил, L-циклоалкенил, -L-моноциклическое кислородсодержащее насыщенное гетерокольцо, -L-моноциклическое азотсодержащее насыщенное гетерокольцо, -L- азотсодержащее насыщенное гетерокольцо, содержащее мостиковую связь, -L-фенил или -L-пиридил, при условии, что тип кольца A, когда R1 представляет собой низший алкил, подразумевает кольцо, которое образует индолин, тетрагидрохинолин или 3,4-дигидро-2H-1,4-бензоксазин вместе с бензольным кольцом, с которым оно конденсировано,
где низший алкил в группе R1 может быть замещен 1-3 группами, выбранными из групп, представленных в описанной ниже группе G, и циклоалкил, циклоалкенил, моноциклическое кислородсодержащее насыщенное гетерокольцо, моноциклическое азотсодержащее насыщенное гетерокольцо, фенил и пиридил в группе R1 могут быть замещены 1-5 группами, выбранными из групп, представленных ниже в определении группы G, и низшего алкила, который может быть замещен группой, представленной в определении группы G,
группа G - -O-низший алкил, -OH, оксо, -S(O)p-низший алкил, -NR4R5, -NR6-CO2-низший алкил, -NR6-SO2-низший алкил, -N+(низший алкил)3, -CO2-низший алкил, -CO-NR4R5, галоген, фенил, циклоалкил, -O-низший алкилен-фенил, -NR6-циклоалкил и моноциклическое кислородсодержащее насыщенное гетерокольцо,
p - 0, 1 или 2,
L - связь или низший алкилен,
R2 - одинаковые или отличные друг от друга и каждый представляет собой H, низший алкил, галоген, галоген-низший алкил или -OH, и
n - 1 или 2.
2. Ингибитор активации VR1, который включает 2-аминобензамидное производное или его соль в качестве активного ингредиента, по п.1, где A представляет собой моноциклическое азотсодержащее гетерокольцо, где указанная кольцевая группа содержит оксогруппу или гидроксильную группу в качестве группы заместителя и может быть дополнительно замещена 1 или 2 группами, выбранными из групп -низший алкилен-OH, -низший алкилен-NR4R5, -низший алкилен-CO-NR4R5, галоген, галоген-низший алкил и низший алкил.
3. 2-Аминобензамидное производное общей формулы (I') или его соль
где X и W - один представляет собой N, а другой представляет собой CH или оба представляют собой CH,
R3a и R3b - одинаковые или отличные друг от друга и каждый представляет собой H, галоген, галоген-низший алкил, циано, нитро, низший алкил, -NR4R5, -низший алкилен-NR4R5, -низший алкилен-NR6-CO2-низший алкил, -O-низший алкил, -O-галоген-низший алкил, фенил или тиенил,
R4 и R5 - одинаковые или отличные друг от друга и каждый представляет собой H или низший алкил, где R4 и R5 могут быть объединены со смежным атомом азота с образованием моноциклического азотсодержащего насыщенного гетерокольца, которое может быть замещено низшим алкилом или группой низший алкилен-OH,
R6 - H или низший алкил,
где кольцо, представленное как А, может быть замещено 1-4 группами, выбранными из групп -OH, -низший алкилен-OH, -низший алкилен-NR4R5, -низший алкилен-CO-NR4R5, галоген, галоген-низший алкил, низший алкил и оксо,
R1 - низший алкил, циклоалкил, циклоалкенил, моноциклическое кислородсодержащее насыщенное гетерокольцо, моноциклическое азотсодержащее насыщенное гетерокольцо, фенил или пиридил, при условии, что тип кольца A, когда R1 представляет собой низший алкил, подразумевает кольцо, которое образует индолин, тетрагидрохинолин или 3,4-дигидро-2H-1,4-бензоксазин вместе с бензольным кольцом, с которым оно конденсировано,
где низший алкил в группе R1 может быть замещен 1-3 группами, выбранными из групп, представленных ниже в определении группы G, и циклоалкил, циклоалкенил, моноциклическое кислородсодержащее насыщенное гетерокольцо, моноциклическое азотсодержащее насыщенное гетерокольцо, фенил и пиридил в группе R1 могут быть замещены 1-5 группами, выбранными из групп, представленных ниже в определении группы G, и низшего алкила, который может быть замещен группой, представленной в определении группы G,
группа G - -O-низший алкил, -OH, оксо, -S(O)p-низший алкил, -NR4R5, -NR6-CO2-низший алкил, -NR6-SO2-низший алкил, -N+(низший алкил)3, -CO2-низший алкил, -CO-NR4R5, галоген, фенил, циклоалкил, -O-низший алкилен-фенил, -NR6-циклоалкил и моноциклическое кислородсодержащее насыщенное гетерокольцо,
p - 0, 1 или 2,
R2 - одинаковые или отличные друг от друга и каждый представляет собой H, низший алкил, галоген, галоген-низший алкил или -OH, и
n - 1 или 2.
4. Производное и его соль по п.3, где X представляет собой N или CH, W представляет собой CH и A представляет собой моноциклическое азотсодержащее гетерокольцо, где указанная кольцевая группа содержит оксогруппу или гидроксильную группу в качестве группы заместителя и может быть дополнительно замещена 1 или 2 группами, выбранными из группы, содержащей -низший алкилен-OH, -низший алкилен-NR4R5, -низший алкилен-CO-NR4R5, галоген, галоген-низший алкил и низший алкил.
5. Производное и его соль по п.4, где тип кольца A представляет собой кольцо, которое образует индолин, тетрагидрохинолин или 3,4-дигидро-2H-1,4-бензоксазин вместе с бензольным кольцом, с которым оно конденсировано.
6. Производное и его соль по п.5, где R1 представляет собой кольцевую группу, выбранную из циклоалкила, циклоалкенила, моноциклического кислородсодержащего насыщенного гетерокольца и моноциклического азотсодержащего насыщенного гетерокольца, которое может быть замещено 1-5 группами, выбранными из групп, представленных в определении группы G, и низшего алкила, который может быть замещен группой, представленной в определении группы G.
7. Производное и его соль по п.6, где R1 представляет собой кольцевую группу, выбранную из циклоалкила, диоксоланила и пиперидила, которая может быть замещена низшим алкилом, -NR4R5 или циклоалкилом.
8. Производное и его соль по п.4, где R1 представляет собой кольцевую группу, выбранную из циклоалкила, циклоалкенила, моноциклического кислородсодержащего насыщенного гетерокольца, моноциклического азотсодержащего насыщенного гетерокольца, фенила и пиридила, которая может быть замещена 1-5 группами, выбранными из групп, представленных в определении группы G, и низшего алкила, который может быть замещен группой, представленной в определении группы G.
9. Производное и его соль по п.8, где R1 представляет собой кольцевую группу, выбранную из циклоалкила, диоксоланила и пиперидила, которая может быть замещена низшим алкилом, -NR4R5 или циклоалкилом.
10. Производное по п.3 или его фармацевтически приемлемая соль, выбранные из группы, включающей 4-хлор-N-(1-метил-2-оксо-1,2,3,4-тетрагидрохинолин-7-ил)-2-{[(1S,2S)-2-пирролидин-1-илциклогексил]амино}бензамид, 2-(циклогексиламино)-N-(2-метил-3-оксо-3,4-дигидро-2H-1,4-бензоксазин-6-ил)-4-(трифторметил)бензамид, 4-хлор-N-[(2R)-2-метил-3-оксо-3,4-дигидро-2H-1,4-бензоксазин-6-ил]-2-{[(1R,2S)-2-пирролидин-1-илциклогексил]амино}бензамид, N-[2-оксо-4-(трифторметил)-2,3-дигидро-1H-индол-6-ил]-2-{[(1S,2S)-2-пирролидин-1-илциклогексил]амино}-4-(трифторметил)бензамид, N-(1-метил-2-оксо-1,2,3,4-тетрагидрохинолин-7-ил)-2-(пиридин-4-иламино)-4-(трифторметил)бензамид, N-(3,3-диметил-2-оксо-2,3-дигидро-1H-индол-6-ил)-2-{[(1S,2S)-2-пирролидин-1-илциклогексил]амино}-4-(трифторметил)бензамид, N-(3,3-диметил-2-оксо-2,3-дигидро-1H-индол-6-ил)-2-{[(1R,2R)-2-пирролидин-1-илциклогексил]амино}-4-(трифторметил)бензамид, 2-{[(1R,2R)-2-(диметиламино)циклогексил]амино}-N-[(2R)-2-метил-3-оксо-3,4-дигидро-2H-1,4-бензоксазин-6-ил]-4-(трифторметил)бензамид, 2-{[(1S,2S)-2-(диметиламино)циклогексил]амино}-N-(3,3-диметил-2-оксо-2,3-дигидро-1H-индол-6-ил)-4-(трифторметил)бензамид, N-(3,3-диметил-2-оксо-2,3-дигидро-1H-индол-6-ил)-2-[(1-изобутилпиперидин-4-ил)амино]-4-(трифторметил)бензамид, N-(3,3-диметил-2-оксо-2,3-дигидро-1H-индол-6-ил)-2-{[(3S)-1-пентилпирролидин-3-ил]амино}-4-(трифторметил)бензамид, N-(2-оксо-1,2-дигидрохинолин-7-ил)-2-{[(1R,2R)-2-пирролидин-1-илциклогексил]амино}-4-(трифторметил)бензамид, N-(3,3-диметил-2-оксо-2,3-дигидро-1H-индол-6-ил)-2-{[(3S)-1-пентилпирролидин-3-ил]амино}-4-(трифторметил)бензамид, 2-[(1-бутилпиперидин-4-ил)амино]-N-(3,3-диметил-2-оксо-2,3-дигидро-1-H-индол-6-ил)-4-(трифторметил)бензамид, N-(3,3-диметил-2-оксо-2,3-дигидро-1H-индол-6-ил)-2-{[(1S,2R)-2-пирролидин-1-илциклогексил]амино}-4-(трифторметил)бензамид, 2-{[(1S,2R)-2-пирролидин-1-илциклогексил]амино}-N-хинолин-7-ил-4-(трифторметил)бензамид, 2-{[(1S,2S)-2-пирролидин-1-илциклогексил]амино}-N-хинолин-7-ил-4-(трифторметил)бензамид и N-[2-оксо-4-(трифторметил)-2,3-дигидро-1H-индол-6-ил]-2-{[(1S,2R)-2-пирролидин-1-илциклогексил]амино}-6-(трифторметил)никотинамид.
11. Фармацевтическая композиция, которая включает производное по п.3 или его фармацевтически приемлемую соль и фармацевтически приемлемый носитель.
12. Фармацевтическая композиция по п.11, которая представляет собой ингибитор активации VR1.
13. Фармацевтическая композиция по п.11, которая представляет собой средство для лечения или предупреждения ноцицептивной боли, невропатической боли, раковой боли, головной боли, расстройства функции мочевого пузыря.
14. Применение производного по п.3 или его фармацевтически приемлемой соли для получения средства для лечения или предупреждения ноцицептивной боли, невропатической боли, раковой боли, головной боли, расстройства функции мочевого пузыря.
15. Способ лечения или предупреждения ноцицептивной боли, невропатической боли, раковой боли, головной боли, расстройства функции мочевого пузыря, который включает введение терапевтически эффективного количества производного по п.2 или его фармацевтически приемлемой соли пациенту.
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AU2006319916A1 (en) | 2007-06-07 |
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