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 OBTAININGInfo
- 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
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compound
- group
- physiologically
- solvate
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 230000001225 therapeutic Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 12
- 239000011780 sodium chloride Substances 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- ULSDMUVEXKOYBU-UHFFFAOYSA-N 4-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-1,3-oxazolidin-2-one Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CC1COC(=O)N1 ULSDMUVEXKOYBU-UHFFFAOYSA-N 0.000 claims 2
- 206010027599 Migraine Diseases 0.000 claims 2
- 208000008085 Migraine Disorders Diseases 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- OOOAMVGIUWTNRH-UHFFFAOYSA-N 4-[[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]methyl]-1,3-oxazolidin-2-one Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2CC1NC(=O)OC1 OOOAMVGIUWTNRH-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 230000000875 corresponding Effects 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 230000000069 prophylaxis Effects 0.000 claims 1
- 0 Cc1ccc2[n]cc(*)c2c1 Chemical compound Cc1ccc2[n]cc(*)c2c1 0.000 description 1
Claims (14)
в которой n является целым числом от 0 до 3, W является группой формулы (i), (ii) или (iii)
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)
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)
in which n is an integer from 0 to 3, W is a group of formula (i), (ii) or (iii)
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)
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.
в которой n является целым числом от 0 до 3, W является группой формулы (i), (ii) или (iii)
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)
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)
где n и W имеют определенные выше значения, с соединением формулы (III)
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)
где n и W имеют определенные выше значения,
с соединением формулы (ХХУIII)
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)
или (ХХУ)
где n, R и Х имеют определенные выше значения, а Z является группой формулы (vi),
с соединением формулы (У11)
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)
in which n is an integer from 0 to 3, W is a group of formula (i), (ii) or (iii)
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)
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)
where n and W are as defined above, with a compound of formula (III)
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
where n and W are as defined above,
with the compound of the formula (XXYIII)
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
or (xxx)
where n, R and X are as defined above, and Z is a group of formula (vi),
with the compound of the formula (Y11)
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.
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 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU501147304 Addition | 1992-02-06 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU95112537A true RU95112537A (en) | 1997-08-10 |
RU2160736C2 RU2160736C2 (en) | 2000-12-20 |
Family
ID=26297174
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU95112537/04A RU2160736C2 (en) | 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 |
Country Status (37)
Country | Link |
---|---|
US (3) | US5399574A (en) |
EP (2) | EP0636623B1 (en) |
JP (1) | JP2738461B2 (en) |
KR (1) | KR100215627B1 (en) |
AT (2) | ATE156823T1 (en) |
AU (1) | AU646871B2 (en) |
CA (2) | CA2282890C (en) |
CZ (1) | CZ288351B6 (en) |
DE (3) | DE69127260T2 (en) |
DK (1) | DK0486666T3 (en) |
EG (1) | EG19650A (en) |
ES (1) | ES2104708T3 (en) |
FI (3) | FI105686B (en) |
GR (1) | GR3024828T3 (en) |
HK (1) | HK1000534A1 (en) |
HR (1) | HRP940524B1 (en) |
HU (2) | HU219974B (en) |
IE (1) | IE911931A1 (en) |
IL (3) | IL98392A (en) |
LT (1) | LT3264B (en) |
LU (1) | LU90205I2 (en) |
LV (1) | LV10274B (en) |
MC (1) | MC2210A1 (en) |
MX (1) | MX9203421A (en) |
MY (1) | MY110226A (en) |
NL (1) | NL980001I2 (en) |
NO (2) | NO300634B1 (en) |
NZ (1) | NZ238424A (en) |
PL (1) | PL166214B1 (en) |
PT (1) | PT97888B (en) |
RU (1) | RU2160736C2 (en) |
SA (1) | SA05260104B1 (en) |
SI (2) | SI21560B (en) |
SK (1) | SK281621B6 (en) |
UA (1) | UA37178C2 (en) |
WO (1) | WO1991018897A1 (en) |
YU (1) | YU48855B (en) |
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- 1991-06-06 WO PCT/GB1991/000908 patent/WO1991018897A1/en active IP Right Grant
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1992
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1994
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