IE33474L - Quinoline derivatives - Google Patents
Quinoline derivativesInfo
- Publication number
- IE33474L IE33474L IE690903A IE90369A IE33474L IE 33474 L IE33474 L IE 33474L IE 690903 A IE690903 A IE 690903A IE 90369 A IE90369 A IE 90369A IE 33474 L IE33474 L IE 33474L
- Authority
- IE
- Ireland
- Prior art keywords
- propionic acid
- chloro
- ethyl ester
- benzoyl
- compounds
- Prior art date
Links
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title abstract 3
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 11
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 229920002554 vinyl polymer Polymers 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- -1 methylenedioxy Chemical group 0.000 abstract 2
- 150000003248 quinolines Chemical class 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 abstract 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
- 230000000078 anti-malarial effect Effects 0.000 abstract 1
- 239000003430 antimalarial agent Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1,253,741. Quinoline derivatives. F. HOFFMANN-LA ROCHE & CO. A.G. 2 July, 1969 [2 July, 1968], No. 33311/69. Heading C2C. Quinoline derivatives of the Formulµ I and II: wherein E 1 is H, OH, halogen, C 1-7 alkyl, C 1-7 alkoxy or methylenedioxy, R 2 is C 1-7 alkyl or C 2-7 alkenyl and m is 1 or 2, with the proviso that when R 1 is methylenedioxy m is 1, the compounds of Formulµ I and II being novel provided that when (R 1 ) m is H, OH or C 1-7 alkoxy in position 6, R 2 is other than vinyl or ethyl, and their antipodes and racemates and acid addition salts thereof are prepared by treating compounds of Formulµ V and VI: these compounds being novel provided that when (R 1 ) m is H, OH or OCH 3 in position- 6, R 2 is other than vinyl or ethyl, their racemates or antipodes thereof with a stereoselective reducing agent, if desired reducing any compound obtained in which R 2 is C 2-7 alkenyl to give corresponding compounds in which R 2 is C 2-7 alkyl, and also, if desired, converting bases obtained into acid addition salts. Compounds of Formulµ V and VI above are obtained by cyclizing compounds of the general Formula IV: X is halogen, with the proviso that when (R 1 ) m is H or OCH 3 in position 6 and R 2 is vinyl or ethyl, X is other than bromine, or antipodes or racemates thereof, or compound of general Formula X above, where R<SP>1</SP> 2 is C 1-7 alkyl or antipodes or racemates thereof, or compounds of the general Formula X above, wherein R is H or C 1-5 alkyl or antipodes or racemates thereof, by means of a cyclization agent, dehalogenating the product obtained from compounds of Formula Xa or antipodes or racemates thereof and, if desired, converting the so-obtained bases into acid addition salts. The following intermediates are prepared:- α - [1 - Benzoyl - 3 - ethyl - 4 - piperidylmethyl]- # - oxo - # - (7 - methoxy - 4 - quinolyl)propionic acid ethyl ester, α-[1-benzoyl-3-ethyl-4-piperidylmethyl] - # - oxo - # - (6,7 - dimethoxy - 4- quinolyl)propionic acid ethyl ester, α-[1-benzoyl - 3 - ethyl - 4 - piperidylmethyl] - # - oxo - #- (6 - methyl - 4 - quinolyl)propionic acid ethyl ester, α - [1 - benzoyl - 3 - ethyl - 4 - piperidylmethyl] - # - oxo - # - (6 - chloro - 4 - quinolyl)propionic acid ethyl ester, α-[l-benzoyl-3-ethyl-4- piperidylmethyl] - # - oxo - # - (7 - chloro - 4- quinolyl)propionic acid ethyl ester, α-[1-benzoyl - 3 - vinyl - 4 - piperidylmethyl]- # - oxo - #- (7 - chloro - 4 - quinolyl)propionic acid ethyl ester, 7<SP>1</SP> - methoxydihydrocinchotoxine, 6<SP>1</SP>,7<SP>1</SP>- dimethoxy - dihydrocinchotoxine, 6<SP>1</SP> - dimethyldihydrocinchotoxine, 6<SP>1</SP> - chlorodihydrocinchotoxine, 7<SP>1</SP> - chlorodihydrocinchotoxine, 7<SP>1</SP>- chlorocinchotoxine, N - chlorodihydroquinotoxine, N - chloro - 7<SP>1 </SP>- methoxydihydrocinchotoxine, N - chloroquinotoxine, N - chloro - 6<SP>1</SP>,7<SP>1</SP>- dimethoxydihydrocinchotoxine, N - chloro- 6<SP>1</SP> - methyldihydrocinchotoxine, N - chloro - 6<SP>1</SP>- chlorodihydrocinchotoxine, N - chloro - 7<SP>1</SP>- chlorodihydrocinchotoxine, N - chloro - 7<SP>1</SP>- chlorocinchotoxine, 3 - (1 - chloro - 3 - ethyl- 4 - piperidine)propionic acid ethyl ester, 3- [3 - (2 - chloroethyl) - 4 - piperidine]propionic acid ethyl ester trifluoroacetate, 3-[1-benzoyl-3- (2 - chloroethyl) - 4 - piperidine]propionic acid ethyl ester, 3-[1-benzoyl-3-(2-iodoethyl)-4-piperidine]propionic acid ethyl ester, and 3-[1- benzoyl - 3 - vinyl - 4 - piperidine]propionic acid ethyl ester. The above intermediates are obtained in one or more of the possible configurations. Pharmaceutical compositions, having antimalarial and antiarrhythmic properties, contain the above novel compounds of Formulµ I, II, V and VI, or acid addition salts thereof, in association with compatible pharmaceutical carriers. The compositions may be in a forms suitable for oral, parenteral or rectal administration.
[GB1253741A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74191368A | 1968-07-02 | 1968-07-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33474L true IE33474L (en) | 1970-01-02 |
| IE33474B1 IE33474B1 (en) | 1974-07-10 |
Family
ID=24982727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE903/69A IE33474B1 (en) | 1968-07-02 | 1969-07-02 | A process for the manufacture of quinoline derivatives |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS4915278B1 (en) |
| AT (2) | AT319481B (en) |
| BE (1) | BE735450A (en) |
| CA (2) | CA956312A (en) |
| CH (2) | CH521975A (en) |
| DE (2) | DE1933599A1 (en) |
| DK (2) | DK136069B (en) |
| FR (1) | FR2012151A1 (en) |
| GB (1) | GB1253741A (en) |
| IE (1) | IE33474B1 (en) |
| IL (1) | IL32534A (en) |
| NL (1) | NL166475C (en) |
| PH (1) | PH12608A (en) |
| SE (2) | SE367823B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH590275A5 (en) * | 1970-03-16 | 1977-07-29 | Hoffmann La Roche | |
| GB1441244A (en) * | 1972-11-17 | 1976-06-30 | Rech Et Dapplications Scient S | Derivatives of quinoline and method of preparing the same |
| NL7908031A (en) * | 1979-11-01 | 1981-06-01 | Acf Chemiefarma Nv | NEW QUINOLINE DERIVATIVES AND PHARMACEUTICAL PREPARATIONS CONTAINING SUCH A COMPOUND AND METHOD FOR PREPARING THESE COMPOUNDS. |
| FR2844270B1 (en) | 2002-09-11 | 2006-05-19 | Aventis Pharma Sa | QUINOLYL PROPYL PIPERIDINE DERIVATIVES, THEIR PROCESS AND PREPARATION INTERMEDIATES AND THE COMPOSITIONS CONTAINING THEM |
| AU2011202542A1 (en) | 2010-07-14 | 2012-02-02 | Indian Institute Of Science | Benzothiophene carboxamide compounds, composition and applications thereof |
-
1969
- 1969-06-26 CH CH977369A patent/CH521975A/en not_active IP Right Cessation
- 1969-06-26 CH CH1402971A patent/CH533123A/en not_active IP Right Cessation
- 1969-07-01 AT AT626969A patent/AT319481B/en not_active IP Right Cessation
- 1969-07-01 BE BE735450D patent/BE735450A/xx not_active IP Right Cessation
- 1969-07-01 FR FR6922135A patent/FR2012151A1/fr not_active Withdrawn
- 1969-07-02 SE SE941269A patent/SE367823B/xx unknown
- 1969-07-02 SE SE7206590A patent/SE375775B/xx unknown
- 1969-07-02 IE IE903/69A patent/IE33474B1/en unknown
- 1969-07-02 DE DE19691933599 patent/DE1933599A1/en not_active Ceased
- 1969-07-02 IL IL32534A patent/IL32534A/en unknown
- 1969-07-02 CA CA055,885A patent/CA956312A/en not_active Expired
- 1969-07-02 DK DK359169AA patent/DK136069B/en not_active IP Right Cessation
- 1969-07-02 GB GB33311/69A patent/GB1253741A/en not_active Expired
- 1969-07-02 DE DE1967178A patent/DE1967178C2/en not_active Expired
- 1969-07-02 NL NL6910144.A patent/NL166475C/en not_active IP Right Cessation
-
1971
- 1971-01-21 AT AT49171A patent/AT341115B/en not_active IP Right Cessation
- 1971-06-04 JP JP46039235A patent/JPS4915278B1/ja active Pending
- 1971-06-23 DK DK308971AA patent/DK136982B/en unknown
- 1971-11-01 CA CA126,551A patent/CA962682A/en not_active Expired
- 1971-12-16 PH PH13115A patent/PH12608A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE33474B1 (en) | 1974-07-10 |
| ATA49171A (en) | 1977-05-15 |
| DK136069C (en) | 1978-01-16 |
| DK136982C (en) | 1978-07-10 |
| IL32534A0 (en) | 1969-09-25 |
| CH533123A (en) | 1973-01-31 |
| AT341115B (en) | 1978-01-25 |
| DK136069B (en) | 1977-08-08 |
| NL166475C (en) | 1981-08-17 |
| CH521975A (en) | 1972-04-30 |
| DE1967178C2 (en) | 1984-11-22 |
| GB1253741A (en) | 1971-11-17 |
| FR2012151A1 (en) | 1970-03-13 |
| SE375775B (en) | 1975-04-28 |
| BE735450A (en) | 1970-01-02 |
| DE1933599A1 (en) | 1970-02-26 |
| AT319481B (en) | 1974-12-27 |
| CA962682A (en) | 1975-02-11 |
| JPS4915278B1 (en) | 1974-04-13 |
| NL6910144A (en) | 1970-01-06 |
| NL166475B (en) | 1981-03-16 |
| SE367823B (en) | 1974-06-10 |
| DK136982B (en) | 1977-12-27 |
| IL32534A (en) | 1975-07-28 |
| CA956312A (en) | 1974-10-15 |
| PH12608A (en) | 1979-06-27 |
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