WO1994001435B1 - New analgesic and nootropic drugs - Google Patents
New analgesic and nootropic drugsInfo
- Publication number
- WO1994001435B1 WO1994001435B1 PCT/EP1993/001743 EP9301743W WO9401435B1 WO 1994001435 B1 WO1994001435 B1 WO 1994001435B1 EP 9301743 W EP9301743 W EP 9301743W WO 9401435 B1 WO9401435 B1 WO 9401435B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- general formula
- naphtyl
- beta
- phenyl
- active ingredient
- Prior art date
Links
- 239000000730 antalgic agent Substances 0.000 title 1
- 239000002664 nootropic agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 11
- -1 CH2OH Chemical group 0.000 claims abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 4
- 125000001424 substituent group Chemical group 0.000 claims abstract 3
- 230000000202 analgesic Effects 0.000 claims abstract 2
- 230000001777 nootropic Effects 0.000 claims abstract 2
- 239000004480 active ingredient Substances 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 238000000034 method Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229960004873 LEVOMENTHOL Drugs 0.000 claims 2
- 229940041616 Menthol Drugs 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N Thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 230000000875 corresponding Effects 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims 1
- 229910006124 SOCl2 Inorganic materials 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 150000001351 alkyl iodides Chemical class 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing Effects 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
Abstract
Compounds of general formula (I), where Ar = phenyl or beta-naphtyl, R1 = one or more substituents of the phenyl or beta-naphtyl nucleus, preferably in para position, and selected out of the group consisting of H, CH3, C(CH3)3, CH2-CH-(CH3)2, O-CH3, C1, F, Br, CF3, NH2, S-CH3, SO-CH3, CN, NO2; R2 = H, CH3, C2H5, CH(CH3)2, CH2OH, C6H5; R3 = (a); where R4 = H, CH3, C2H5, CH(CH3)2, CH2-C6H5; R5 = H, CH3; X = none O, S, NH, NCH3; Y = O, NH, both in the racemic form and in the isomeric enantiomeric forms, which produce a nootropic effect, i.e. memory enhancement and learning facilitation, as well as an analgesic effect.
Claims
AMENDED CLAIMS
[received by the International Bureau on 28 February 1994 (28.02.94);
original claims 1, 5, 6-10 amended; remaining claims unchanged (4 pages)]
1) Compounds of general formula:
R1 = one or more substituents of the phenyl or beta-naphtyl nucleus, preferably in para position, and selected out of the group consisting of H, CH3. CH2-CH-(CH3)2, O-CHo, CI,
F, Br, CF3, NH2, S-CH3, CN, NO2
R2 = H, CH3, C2H5, CH(CH3)2, 
where R4 = H, CH3, C2H5,
R5 = H, CH3
X = O, S, NH, NCH3
Y = O, NH,
both in the racemic form and in the isomeric enantiomeric forms.
2. Compounds according to claim 1, wherein R3 is 3-α-tropanil.
3. Procedure for the preparation of the compounds according to claim 1 consisting in the conversion of the corresponding carboxylic acid
into the chloride by reaction with SOCl2, followed by the reaction of the acyl chloride with compound HYR3 carried out in the presence of basic substances.
4. The procedure according to claim 3. wherein the carboxylic acid of general formula (II) is obtained from α-broπto alkanoic acid of general formula
5. Analgesic and nootropic pharmaceutical compositions containing as active ingredient a compound of general formula:
R1 = one or more substituents of the phenyl or beta-naphtyl nucleus, preferably in para position, and selected out of the group consisting of H, CH3, CH2-CH-(CH3)2, O-CH3, CI,
F, Br, CF3, NH2, S-CH3, CN, N02
R2 = H, CH3, C2H5, CH(CH3)2, 
where R4 = H, CH3, C2H5, R5 = H, CH3
X = none O, S, NH, NCH3
Y = O, NH,
both in the racemic form and in the isomeric enantiomeric forms.
6. Procedure for the preparation of the compounds according to claim 5. wherein X is absent and R5=H, characterized in that the intermediate compound of general formula
with menthol, by alkylation of the menthol ester with alkyl iodide R2I, and finally by hydrolizing the alkylated menthol ester.
7 . The pharmaceutical compositions according to claim 5, containing suitable excipients for administration by the oral, intramuscular, subcutaneous, intravenous ways or as suppositories.
8. The composition according to claim 5, wherein the active ingredient is the following compound
9. The composition according to claim 5, wherein the active ingredient is the following compound
10. The pharmaceutical compositions according to claim 5, wherein the active ingredient is the following compound
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SK18-95A SK1895A3 (en) | 1992-07-08 | 1993-07-06 | Analgetic and nootropic drugs |
| KR1019950700071A KR100258336B1 (en) | 1992-07-08 | 1993-07-06 | New analgesic and nootropic drugs |
| AU45645/93A AU4564593A (en) | 1992-07-08 | 1993-07-06 | New analgesic and nootropic drugs |
| EP93915808A EP0650486A1 (en) | 1992-07-08 | 1993-07-06 | New analgesic and nootropic drugs |
| JP6502940A JPH07508739A (en) | 1992-07-08 | 1993-07-06 | Novel analgesic and nootropic agents |
| FI950029A FI950029A (en) | 1992-07-08 | 1995-01-03 | New analgesic and nootropic drugs |
| NO950053A NO307518B1 (en) | 1992-07-08 | 1995-01-06 | Therapeutically active compound for the treatment of cognitive deficits and pain |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI92A001659 | 1992-07-08 | ||
| ITMI921659A IT1255323B (en) | 1992-07-08 | 1992-07-08 | COMPOUNDS WITH ANALGESIC AND NOOTROP ACTIVITY |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1994001435A1 WO1994001435A1 (en) | 1994-01-20 |
| WO1994001435B1 true WO1994001435B1 (en) | 1994-03-31 |
Family
ID=11363636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1993/001743 WO1994001435A1 (en) | 1992-07-08 | 1993-07-06 | New analgesic and nootropic drugs |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5583142A (en) |
| EP (1) | EP0650486A1 (en) |
| JP (1) | JPH07508739A (en) |
| KR (1) | KR100258336B1 (en) |
| AU (1) | AU4564593A (en) |
| CA (1) | CA2139739A1 (en) |
| CZ (1) | CZ2295A3 (en) |
| FI (1) | FI950029A (en) |
| HU (1) | HUT73481A (en) |
| IT (1) | IT1255323B (en) |
| NO (1) | NO307518B1 (en) |
| RU (1) | RU95105457A (en) |
| SK (1) | SK1895A3 (en) |
| WO (1) | WO1994001435A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5794887A (en) | 1995-11-17 | 1998-08-18 | Komerath; Narayanan M. | Stagnation point vortex controller |
| EP2206712A1 (en) * | 2008-12-23 | 2010-07-14 | CHIESI FARMACEUTICI S.p.A. | "Alkaloid aminoester derivatives and medicinal composition thereof" |
| RU2744571C1 (en) * | 2020-04-10 | 2021-03-11 | Общество с ограниченной ответственностью "ВладМиВа"(ООО "ВладМиВа") | Dipharmacophoric compounds of nootropic-analgesic action and method for their preparation |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1289429A (en) * | 1960-03-10 | 1962-04-06 | Lepetit Spa | Process for the preparation of the new esters of tropine |
| DE1670142A1 (en) * | 1966-09-02 | 1970-07-16 | Boehringer Sohn Ingelheim | Process for the preparation of atropine, scopolamine and their N-substituted derivatives |
| DE4108393A1 (en) * | 1991-03-15 | 1992-09-17 | Boehringer Ingelheim Kg | NEW ESTERS BI-AND TRICYCLIC AMINO ALCOHOLS, THEIR PREPARATION AND THEIR USE IN MEDICINAL PRODUCTS |
-
1992
- 1992-07-08 IT ITMI921659A patent/IT1255323B/en active IP Right Grant
-
1993
- 1993-07-06 RU RU95105457/04A patent/RU95105457A/en unknown
- 1993-07-06 JP JP6502940A patent/JPH07508739A/en active Pending
- 1993-07-06 HU HU9403797A patent/HUT73481A/en unknown
- 1993-07-06 KR KR1019950700071A patent/KR100258336B1/en not_active IP Right Cessation
- 1993-07-06 CA CA002139739A patent/CA2139739A1/en not_active Abandoned
- 1993-07-06 SK SK18-95A patent/SK1895A3/en unknown
- 1993-07-06 CZ CZ9522A patent/CZ2295A3/en unknown
- 1993-07-06 AU AU45645/93A patent/AU4564593A/en not_active Abandoned
- 1993-07-06 EP EP93915808A patent/EP0650486A1/en not_active Ceased
- 1993-07-06 WO PCT/EP1993/001743 patent/WO1994001435A1/en not_active Application Discontinuation
-
1995
- 1995-01-03 FI FI950029A patent/FI950029A/en unknown
- 1995-01-06 NO NO950053A patent/NO307518B1/en not_active IP Right Cessation
- 1995-01-06 US US08/369,761 patent/US5583142A/en not_active Expired - Fee Related
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