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RU95112537A - THERAPEUTIC HETEROCYCLIC COMPOUNDS, METHOD FOR THEIR PRODUCTION, PHARMACEUTICAL COMPOSITION, METHOD FOR ITS OBTAINING - Google Patents

THERAPEUTIC HETEROCYCLIC COMPOUNDS, METHOD FOR THEIR PRODUCTION, PHARMACEUTICAL COMPOSITION, METHOD FOR ITS OBTAINING

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Publication number
RU95112537A
RU95112537A RU95112537/04A RU95112537A RU95112537A RU 95112537 A RU95112537 A RU 95112537A RU 95112537/04 A RU95112537/04 A RU 95112537/04A RU 95112537 A RU95112537 A RU 95112537A RU 95112537 A RU95112537 A RU 95112537A
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RU
Russia
Prior art keywords
formula
compound
group
physiologically
solvate
Prior art date
Application number
RU95112537/04A
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Russian (ru)
Other versions
RU2160736C2 (en
Inventor
Дункан Робертсон Алан
Питер Хилл Алан
Чарльз Глен Роберт
Ричард Мартин Грэм
Original Assignee
Дзе Веллкам Фаундейшн Лимитед
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Priority claimed from GB909012672A external-priority patent/GB9012672D0/en
Priority claimed from GB919102182A external-priority patent/GB9102182D0/en
Application filed by Дзе Веллкам Фаундейшн Лимитед filed Critical Дзе Веллкам Фаундейшн Лимитед
Publication of RU95112537A publication Critical patent/RU95112537A/en
Application granted granted Critical
Publication of RU2160736C2 publication Critical patent/RU2160736C2/en

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Claims (14)

1. Соединение формулы (I)
Figure 00000001

в которой n является целым числом от 0 до 3, W является группой формулы (i), (ii) или (iii)
Figure 00000002

в которой R является водородом или С1-C4-алкилом, Х является -О-, -S-, -NН- или -СН2-, Y является кислородом или серой, а хиральный центр* в формуле (i) или (ii) находится в своей (S)- или (R)-форме или является смесью их в любых соотношениях; Z является группой формулы (iv), (v) или (vi)
Figure 00000003

в которой R1 и R2 независимо выбираются из водорода и С1-C4- алкила, а R3 является водородом или С1-C4-алкилом, и соли, сольваты и физиологически функциональные производные его при условии, что исключается соединение: N, N-диметил-2-[5-(2-оксо-1,3-оксазолидин-4-ил-метил)-1Н-индол-3-ил]-этиламин.1. The compound of formula (I)
Figure 00000001

in which n is an integer from 0 to 3, W is a group of formula (i), (ii) or (iii)
Figure 00000002

in which R is hydrogen or C 1 -C 4 -alkyl, X is -O-, -S-, -NH- or -CH 2 -, Y is oxygen or sulfur, and a chiral center * in the formula (i) or ( ii) is in its (S) - or (R) -form or is a mixture of them in any ratios; Z is a group of formula (iv), (v) or (vi)
Figure 00000003

in which R 1 and R 2 are independently selected from hydrogen and C 1 -C 4 is alkyl, and R 3 is hydrogen or C 1 -C 4 -alkyl, and salts, solvates and physiologically functional derivatives thereof, provided that the compound is excluded: N, N-dimethyl-2- [5- (2-oxo-1,3-oxazolidin-4-ylmethyl) -1H-indol-3-yl] -ethylamine. 2. Соединение формулы (I) по п. 1, отличающееся тем, что n является 1, или W является группой формулы (i), или Z является группой формулы (iv) или (vi), и физиологически приемлемые соли, сольваты и физиологически функциональные производные его. 2. The compound of formula (I) according to claim 1, characterized in that n is 1, or W is a group of formula (i), or Z is a group of formula (iv) or (vi), and physiologically acceptable salts, solvates and physiologically functional derivatives of it. 3. Соединение формулы (I) по п. 1, отличающееся тем, что n является 0, W является группой формулы (i), где R является водородом, Х является -O-, а Y является кислородом, и Z является группой формулы (iv) или (vi), где R1 = R2 - водород или метил, и физиологически приемлемые соли, сольваты и физиологически функциональные производные его.3. The compound of formula (I) according to claim 1, characterized in that n is 0, W is a group of formula (i), where R is hydrogen, X is -O-, and Y is oxygen, and Z is a group of formula ( iv) or (vi), where R 1 = R 2 is hydrogen or methyl, and physiologically acceptable salts, solvates and physiologically functional derivatives thereof. 4. Соединение формулы (I) по п. 1, отличающееся тем, что соединением является 3-(1-метил-4-пиперидил)-5-(2-оксо-1,3-оксазолидин-4-ил-метил)-1H-индол или в его (S)- или (R)-форме, или в виде смеси их в любых соотношениях, или физиологически приемлемой солью, сольватом или физиологически функциональным производным их. 4. The compound of formula (I) under item 1, characterized in that the compound is 3- (1-methyl-4-piperidyl) -5- (2-oxo-1,3-oxazolidin-4-yl-methyl) - 1H-indole or in its (S) - or (R) -form, or in the form of a mixture of them in any ratios, or a physiologically acceptable salt, solvate or physiologically functional derivative of them. 5. Соединение формулы (I) по любому из пп. 1 - 4, или физиологически приемлемая соль, сольват или физиологически функциональное производное его, для использования в качестве лекарственного средства. 5. The compound of formula (I) according to any one of paragraphs. 1 to 4, or a physiologically acceptable salt, solvate, or physiologically functional derivative thereof, for use as a medicine. 6. Соединение формулы (I) по любому из пп. 1 - 4, или физиологически приемлемая соль, сольват или физиологически функциональное производное его, для использования при профилактике или лечении клинического состояния, для которого показано применение агониста для "5-НТ1-подобного" рецептора.6. The compound of formula (I) according to any one of paragraphs. 1 to 4, or a physiologically acceptable salt, solvate, or physiologically functional derivative thereof, for use in the prophylaxis or treatment of a clinical condition for which the use of an agonist for the “5-HT 1 -like” receptor is indicated. 7. Соединение формулы (I) по любому из пп. 1 - 4 или физиологически приемлемая соль, сольват или физиологически функциональное производное его, для использования при профилактике или лечении мигрени. 7. The compound of formula (I) according to any one of paragraphs. 1 to 4 or a physiologically acceptable salt, solvate or physiologically functional derivative thereof, for use in the prevention or treatment of migraine. 8. Соединение формулы (I) по любому из пп. 1 - 4, или физиологически приемлемая соль, сольват или физиологически функциональное производное его, используемое при изготовлении лекарственного средства для профилактики или лечения клинического состояния, для которого показан агонист для "5-НТ1-подобного" рецептора.8. The compound of formula (I) according to any one of paragraphs. 1 to 4, or a physiologically acceptable salt, solvate, or physiologically functional derivative thereof, used in the manufacture of a medicament for the prevention or treatment of a clinical condition for which an agonist is indicated for a "5-HT 1 -like" receptor. 9. Соединение формулы (I) по любому из пп. 1 - 4, или физиологически приемлемая соль, сольват или физиологически функциональное производное его, используемое при изготовлении лекарственного средства для профилактики или лечения мигрени. 9. The compound of formula (I) according to any one of paragraphs. 1 to 4, or a physiologically acceptable salt, solvate, or physiologically functional derivative thereof, used in the manufacture of a medicament for the prevention or treatment of migraine. 10. Лекарственное средство, отличающееся тем, что в качестве активного компонента включает эффективное количество соединения формулы (I) по любому из пп. 1 - 4, или физиологически приемлемую соль, сольват или физиологически функциональное производное его, фармацевтически приемлемый носитель и, необязательно, одно или более других физиологически активных средств. 10. Drug, characterized in that as the active component includes an effective amount of the compounds of formula (I) according to any one of paragraphs. 1 to 4, or a physiologically acceptable salt, solvate, or physiologically functional derivative thereof, a pharmaceutically acceptable carrier, and, optionally, one or more other physiologically active agents. 11. Средство по п. 10 в форме таблетки или капсулы. 11. Means under item 10 in the form of a tablet or capsule. 12. Способ получения соединения формулы (I)
Figure 00000004

в которой n является целым числом от 0 до 3, W является группой формулы (i), (ii) или (iii)
Figure 00000005

где R является водородом или С1-С4-алкилом, Х является -О-, -S-, -NН- или -CH2-, Y является кислородом или серой, а хиральный центр * в формуле (i) или (ii) находится в его (S)- или (R)-форме или является смесью их в любых соотношениях; и Z является группой формулы (iv), (v) или (vi)
Figure 00000006

где R1 и R2 независимо выбираются из водорода и С1-C4-алкила, а R3 является водородом или С1-C4-алкилом, при условии, что исключается соединение N, N-диметил-2-[5-(2-оксо-1,3-оксазолидин-4-ил-метил)-1Н-индол-3-ил] -этиламин, отличающийся тем, что (а) в случае, когда Z является группой формулы (iv), осуществляют реакцию соединения формулы (II)
Figure 00000007

где n и W имеют определенные выше значения, с соединением формулы (III)
Figure 00000008
или с карбонил-защищенной формой его, где L является подходящей удаляемой группой или защищенной аминогруппой, которая может быть превращена in situ в аминогруппу или является группой -NR1R2, где R1 и R2 имеют определенные выше значения; (б) в случае, когда Z является группой формулы (V), проводят реакцию соединения формулы (XXXI)
Figure 00000009

где n и W имеют определенные выше значения,
с соединением формулы (ХХУIII)
Figure 00000010

где R3 имеет определенные выше значения, и (в) в случае, когда Z является группой формулы (vi), восстанавливают соединение формулы (I), в которой n и W имеют определенные выше значения, а Z является группой формулы (V), или в случае, когда Y является группой формулы (i) или (ii), проводят реакцию соединения формулы (ХУ)
Figure 00000011

или (ХХУ)
Figure 00000012

где n, R и Х имеют определенные выше значения, а Z является группой формулы (vi),
с соединением формулы (У11)
Figure 00000013

где Y имеет определенные выше значения, а L и L1, которые могут быть одинаковыми или различными, являются подходящими уходящими группами, и необязательно превращают соединение формулы (I), полученное таким образом, в соответствующую соль, сольват или физиологически функциональное производное его.12. The method of obtaining the compounds of formula (I)
Figure 00000004

in which n is an integer from 0 to 3, W is a group of formula (i), (ii) or (iii)
Figure 00000005

where R is hydrogen or C 1 -C 4 -alkyl, X is -O-, -S-, -NH- or -CH 2 -, Y is oxygen or sulfur, and the chiral center * in the formula (i) or (ii ) is in its (S) - or (R) -form or is a mixture of them in any ratios; and Z is a group of formula (iv), (v) or (vi)
Figure 00000006

where R 1 and R 2 are independently selected from hydrogen and C 1 -C 4 -alkyl, and R 3 is hydrogen or C 1 -C 4 -alkyl, provided that the compound N, N-dimethyl-2- [5- (2-oxo-1,3-oxazolidin-4-yl-methyl) -1H-indol-3-yl] -ethylamine, characterized in that (a) when Z is a group of formula (iv), the reaction is carried out compounds of formula (II)
Figure 00000007

where n and W are as defined above, with a compound of formula (III)
Figure 00000008
or with a carbonyl protected form thereof, where L is a suitable leaving group or a protected amino group that can be converted in situ to an amino group or is —NR 1 R 2 , where R 1 and R 2 are as defined above; (b) in the case when Z is a group of formula (V), the compounds of formula (XXXI) are reacted
Figure 00000009

where n and W are as defined above,
with the compound of the formula (XXYIII)
Figure 00000010

wherein R 3 is as defined above, and (c) in the case where Z is a group of formula (vi), the compound of formula (I) is reduced, in which n and W are as defined above, and Z is a group of formula (V), or in the case when Y is a group of formula (i) or (ii), the compounds of formula (XU) are reacted
Figure 00000011

or (xxx)
Figure 00000012

where n, R and X are as defined above, and Z is a group of formula (vi),
with the compound of the formula (Y11)
Figure 00000013

where Y is as defined above, and L and L 1 , which may be the same or different, are suitable leaving groups, and optionally convert the compound of formula (I), thus obtained, to the corresponding salt, solvate or physiologically functional derivative thereof. 13. Способ получения лекарственного средства, отличающийся тем, что (а) получают соединение формулы (I) или его физиологически приемлемую соль, сольват или физиологически функциональное производное его по способу, заявленному в п. 12, и (б) смешивают продукт реакции из стадии (а) с фармацевтически приемлемым носителем и необязательно одним или более другими физиологически активными средствами. 13. The method of obtaining a medicinal product, characterized in that (a) receive a compound of formula (I) or its physiologically acceptable salt, solvate or physiologically functional derivative of it according to the method stated in paragraph 12, and (b) mix the reaction product from stage (a) with a pharmaceutically acceptable carrier and optionally one or more other physiologically active agents. 14. Способ по п. 13, отличающийся тем, что включает дополнительную стадию (в), в которой смеси из стадии (б) придают форму таблетки или капсулы. 14. The method according to p. 13, characterized in that it includes an additional stage (c), in which the mixture from stage (b) is shaped into a tablet or capsule.
RU95112537/04A 1990-06-07 1991-06-06 Indole derivatives and physiologically acceptable salts and solvates thereof, methods of preparing thereof, drug for treatment or prophylaxes of clinical states for which administration of 5-ht1-like receptor agonist, and method of preparing thereof RU2160736C2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB909012672A GB9012672D0 (en) 1990-06-07 1990-06-07 Therapeutic heterocyclic compounds
GB9012672.3 1990-06-07
GB9102182.4 1991-02-01
GB919102182A GB9102182D0 (en) 1991-02-01 1991-02-01 Therapeutic heterocyclic compounds

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