CA1044239A - 6-alkoxy-7-hydroxyquinoline-3-carboxylic acids and derivatives thereof - Google Patents
6-alkoxy-7-hydroxyquinoline-3-carboxylic acids and derivatives thereofInfo
- Publication number
- CA1044239A CA1044239A CA207,894A CA207894A CA1044239A CA 1044239 A CA1044239 A CA 1044239A CA 207894 A CA207894 A CA 207894A CA 1044239 A CA1044239 A CA 1044239A
- Authority
- CA
- Canada
- Prior art keywords
- group
- compound
- process according
- formula
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 238000006798 ring closing metathesis reaction Methods 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000002252 acyl group Chemical group 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- -1 ortho-formic acid ester Chemical class 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 3
- 239000011736 potassium bicarbonate Substances 0.000 claims description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical group [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 3
- 229940086066 potassium hydrogencarbonate Drugs 0.000 claims description 3
- YIFCWYUSYGFFMH-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedioic acid Chemical class CCOC=C(C(O)=O)C(O)=O YIFCWYUSYGFFMH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001448 anilines Chemical class 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 230000000875 corresponding effect Effects 0.000 claims 4
- OGFGOEBARPUXOW-UHFFFAOYSA-N ethyl 6-acetyloxy-7-ethoxy-4-oxo-1H-quinoline-3-carboxylate Chemical compound C(C)(=O)OC=1C=C2C(=C(C=NC2=CC1OCC)C(=O)OCC)O OGFGOEBARPUXOW-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 238000006136 alcoholysis reaction Methods 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- AZCOMUGSJJOYHH-UHFFFAOYSA-N diethyl 2-[(3-ethoxy-4-hydroxyanilino)methylidene]propanedioate Chemical compound CCOC(=O)C(=CNC1=CC(OCC)=C(O)C=C1)C(=O)OCC AZCOMUGSJJOYHH-UHFFFAOYSA-N 0.000 claims 1
- GLUQMYQDGHKVIX-UHFFFAOYSA-N ethyl 7-ethoxy-6-hydroxy-4-oxo-1h-quinoline-3-carboxylate Chemical compound CCOC1=C(O)C=C2C(=O)C(C(=O)OCC)=CNC2=C1 GLUQMYQDGHKVIX-UHFFFAOYSA-N 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 239000012188 paraffin wax Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
- 230000002192 coccidiostatic effect Effects 0.000 abstract description 5
- 150000002148 esters Chemical class 0.000 abstract description 4
- 230000002378 acidificating effect Effects 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 241000448280 Elates Species 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000002440 hydroxy compounds Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- GIHYKBDWFSOKNN-UHFFFAOYSA-N 2-ethoxy-4-nitrophenol Chemical compound CCOC1=CC([N+]([O-])=O)=CC=C1O GIHYKBDWFSOKNN-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- FKHZSVWGOFCGCJ-UHFFFAOYSA-N C(C)(=O)OC1=C(C=C(C=C1)[N+](=O)[O-])OCC Chemical compound C(C)(=O)OC1=C(C=C(C=C1)[N+](=O)[O-])OCC FKHZSVWGOFCGCJ-UHFFFAOYSA-N 0.000 description 1
- GAKQMSVBEZWYGU-UHFFFAOYSA-N C(C)(=O)OC1=C(C=C(N)C=C1)OCC Chemical compound C(C)(=O)OC1=C(C=C(N)C=C1)OCC GAKQMSVBEZWYGU-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ZAQRIDPUFKWJDQ-UHFFFAOYSA-N acetic acid;hydrate;hydrochloride Chemical compound O.Cl.CC(O)=O ZAQRIDPUFKWJDQ-UHFFFAOYSA-N 0.000 description 1
- HZWXJJCSDBQVLF-UHFFFAOYSA-N acetoxysulfonic acid Chemical compound CC(=O)OS(O)(=O)=O HZWXJJCSDBQVLF-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000003224 coccidiostatic agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229940058961 hydroxyquinoline derivative for amoebiasis and other protozoal diseases Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—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
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001404 HU167573B (enrdf_load_stackoverflow) | 1973-08-28 | 1973-08-28 | |
| HUCI001403 HU167572B (enrdf_load_stackoverflow) | 1973-08-28 | 1973-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1044239A true CA1044239A (en) | 1978-12-12 |
Family
ID=26318396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA207,894A Expired CA1044239A (en) | 1973-08-28 | 1974-08-27 | 6-alkoxy-7-hydroxyquinoline-3-carboxylic acids and derivatives thereof |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55120566A (en) | 1979-03-09 | 1980-09-17 | Mitsui Toatsu Chem Inc | New quinoline derivative |
| DE4014171A1 (de) * | 1990-05-03 | 1991-11-07 | Basf Ag | Cyanochinolinverbindungen |
-
1974
- 1974-08-23 SE SE7410745A patent/SE406911B/xx unknown
- 1974-08-26 NL NL7411324A patent/NL7411324A/xx not_active Application Discontinuation
- 1974-08-26 PL PL1974187261A patent/PL92578B1/pl unknown
- 1974-08-26 AT AT688374A patent/AT338789B/de not_active IP Right Cessation
- 1974-08-27 GB GB3745174A patent/GB1467225A/en not_active Expired
- 1974-08-27 DK DK454774AA patent/DK141167B/da not_active IP Right Cessation
- 1974-08-27 CH CH1168574A patent/CH615917A5/de not_active IP Right Cessation
- 1974-08-27 NO NO743064A patent/NO145788C/no unknown
- 1974-08-27 CA CA207,894A patent/CA1044239A/en not_active Expired
- 1974-08-27 SU SU7402057994A patent/SU567402A3/ru active
- 1974-08-27 JP JP49098309A patent/JPS5082077A/ja active Pending
- 1974-08-28 DD DD180757A patent/DD114077A1/xx unknown
- 1974-08-28 IN IN1940/CAL/1974A patent/IN140826B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO145788B (no) | 1982-02-22 |
| JPS5082077A (enrdf_load_stackoverflow) | 1975-07-03 |
| GB1467225A (en) | 1977-03-16 |
| DK141167B (da) | 1980-01-28 |
| CH615917A5 (en) | 1980-02-29 |
| DD114077A1 (enrdf_load_stackoverflow) | 1975-07-12 |
| SE7410745L (enrdf_load_stackoverflow) | 1975-03-03 |
| NL7411324A (nl) | 1975-03-04 |
| PL92578B1 (enrdf_load_stackoverflow) | 1977-04-30 |
| IN140826B (enrdf_load_stackoverflow) | 1976-12-25 |
| SE406911B (sv) | 1979-03-05 |
| SU567402A3 (ru) | 1977-07-30 |
| AT338789B (de) | 1977-09-12 |
| DK454774A (enrdf_load_stackoverflow) | 1975-04-28 |
| DK141167C (enrdf_load_stackoverflow) | 1980-06-23 |
| NO145788C (no) | 1982-06-02 |
| ATA688374A (de) | 1977-01-15 |
| NO743064L (enrdf_load_stackoverflow) | 1975-03-24 |
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