GB1205638A - 3-quinoline-carboxylic acid compounds, process for their manufacture and compositions containing them - Google Patents
3-quinoline-carboxylic acid compounds, process for their manufacture and compositions containing themInfo
- Publication number
- GB1205638A GB1205638A GB43549/67A GB4354967A GB1205638A GB 1205638 A GB1205638 A GB 1205638A GB 43549/67 A GB43549/67 A GB 43549/67A GB 4354967 A GB4354967 A GB 4354967A GB 1205638 A GB1205638 A GB 1205638A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- group
- ester
- quinoline
- nitrile
- 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
- 238000000034 method Methods 0.000 title abstract 2
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000003277 amino group Chemical group 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 230000007062 hydrolysis Effects 0.000 abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract 3
- -1 substituted Chemical class 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000005001 aminoaryl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- OONRIDKLOOHJIR-UHFFFAOYSA-N ethyl 4-chloro-6,7-dicyclopropyl-2-methoxyquinoline-3-carboxylate Chemical compound ClC1=C(C(=NC2=CC(=C(C=C12)C1CC1)C1CC1)OC)C(=O)OCC OONRIDKLOOHJIR-UHFFFAOYSA-N 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 abstract 1
- 150000002429 hydrazines Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,205,638. Quinoline-3-carboxylic acids and their derivatives. CIBA Ltd. 25 Sept., 1967 [29 Sept., 1966; 7 April, 1967; 3 July, 1967; 18 August, 1967], No. 43549/67. Heading C2C. [Also in Division A5] Novel compounds of formulµ and 3-esters, 3-amides, 3-hydrazides and 3- nitriles thereof, and 4-esters of the compounds of the second formula, wherein R represents a cycloalkyl or cycloalkenyl radical optionally substituted by aliphatic, aromatic or araliphatic residues or etherified or esterified hydroxyl groups, A represents a direct bond or a C 1- 7 alkylene group, X is O or S, R 2 is H or C 1-7 alkyl, R 3 is H, C 1-7 alkyl, C 1-7 alkenyl, a free, etherified or esterified hydroxy-C 1-7 alkyl, a free or esterified carboxy-C 1-7 alkyl, amino-C 1-7 alkyl, or aryl-C 1-7 alkyl, or a group of the formula R-A-, R and A having the previous significance, and each of the symbols R b and R c represent H, C 1-7 alkyl, a free, etherified or esterified hydroxy or mercapto group, CF 3 , NO 2 , an amino group, or aryl-C 1-7 alkyl, are prepared (a) by ring closing a di-C 1-7 -alkyl ester or a nitrile-C 1-7 -alkyl half ester of an [optionally substituted 1-(cycloaliphatyloxy- or cycloaliphatylthio - phenylamino) alkylmalonic acid which is unsubstituted in one of the positions of the phenyl residue adjacent to the amino group, or a tautomer thereof in which the amino group contains a hydrogen atom, by intramolecular condensation; (b) by converting in an optionally substituted -cycloaliphatyloxy or cycloaliphatylthio - 4 - Y 1 - quinoline - 3 - carboxylic acid or a 3-ester, 3-amide, 3-hydrazide or 3- nitrile of such a compound, in which Y 1 is halo or in a 1-substituted tautomer thereof Y 1 is a functionally converted oxo group capable of being liberated by hydrolysis, the group Y 1 into a hydroxy or an oxo group by hydrolysis; or (c) ring-closing an optionally substituted - cycloaliphatyloxy- or cycloaliphatylthio-oaminobenzoylacetic acid or an amide, ester, hydrazide or nitrile thereof, in which the amino group or the α-position of the acetic acid residue carries a C 1-7 alkanoyl group, by intramolecular condensation and then if desired the functional group in the 3-position can be converted into the free acid, ester, amide, hydrazide, nitrile or salt by conventional methods. Compounds prepared by any of these methods can be converted into other novel compounds defined above by standard methods, for example, by etherification, hydrolysis or transesterification, or by reaction with amines, ammonia, hydrazines or reactive esters. Ethyl 4 - chloro - 6,7 - bis - cyclopropyl - methoxy - quinoline - 3 - carboxylate is formed as a by-product when diethyl (3,4-bis-cyclopropylmethoxy - phenylamino) methylmalonate is reacted with phosphorus oxychloride.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58310166A | 1966-09-29 | 1966-09-29 | |
| US62908567A | 1967-04-07 | 1967-04-07 | |
| US65065567A | 1967-07-03 | 1967-07-03 | |
| US66154167A | 1967-08-18 | 1967-08-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1205638A true GB1205638A (en) | 1970-09-16 |
Family
ID=27504963
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43549/67A Expired GB1205638A (en) | 1966-09-29 | 1967-09-25 | 3-quinoline-carboxylic acid compounds, process for their manufacture and compositions containing them |
| GB2190/70A Expired GB1205639A (en) | 1966-09-29 | 1967-09-25 | Esters of [1-cycloaliphatyloxy- or 1-cycloaliphatylmercaptophenylamino)-1,1-alkylidenej]-malonic acids and process for their manufacture |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2190/70A Expired GB1205639A (en) | 1966-09-29 | 1967-09-25 | Esters of [1-cycloaliphatyloxy- or 1-cycloaliphatylmercaptophenylamino)-1,1-alkylidenej]-malonic acids and process for their manufacture |
Country Status (13)
| Country | Link |
|---|---|
| JP (2) | JPS4827317B1 (en) |
| AT (4) | AT281032B (en) |
| BE (1) | BE704458A (en) |
| CH (3) | CH529136A (en) |
| CS (1) | CS158209B2 (en) |
| DE (1) | DE1670464A1 (en) |
| DK (1) | DK137492B (en) |
| FI (1) | FI48733C (en) |
| FR (1) | FR1578721A (en) |
| GB (2) | GB1205638A (en) |
| IL (1) | IL28656A (en) |
| NL (1) | NL6713219A (en) |
| SE (2) | SE388759B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002052949A1 (en) * | 2001-01-08 | 2002-07-11 | Gormar Marketing Limited | Autoinducer compounds and their uses |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS556193U (en) * | 1978-06-29 | 1980-01-16 | ||
| ATE27451T1 (en) * | 1981-03-24 | 1987-06-15 | Ciba Geigy Ag | ACYL-QUINOLINONE DERIVATIVES, PROCESS FOR THEIR MANUFACTURE, PHARMACEUTICAL PREPARATIONS CONTAINING THEM AND THEIR USE. |
| FR2537140B1 (en) * | 1982-12-07 | 1986-07-18 | Roussel Uclaf | NOVEL 4-HYDROXY-3-QUINOLEINE CARBOXAMIDE DERIVATIVES, SALTS THEREOF, PROCESS FOR THEIR PREPARATION, APPLICATION AS MEDICAMENTS, AND COMPOSITIONS CONTAINING THEM |
-
1967
- 1967-09-18 CH CH59770A patent/CH529136A/en not_active IP Right Cessation
- 1967-09-18 CH CH1300167A patent/CH538476A/en not_active IP Right Cessation
- 1967-09-18 CH CH60570A patent/CH519304A/en not_active IP Right Cessation
- 1967-09-20 IL IL28656A patent/IL28656A/en unknown
- 1967-09-21 DE DE19671670464 patent/DE1670464A1/en active Pending
- 1967-09-25 FI FI672548A patent/FI48733C/en active
- 1967-09-25 GB GB43549/67A patent/GB1205638A/en not_active Expired
- 1967-09-25 GB GB2190/70A patent/GB1205639A/en not_active Expired
- 1967-09-26 FR FR1578721D patent/FR1578721A/fr not_active Expired
- 1967-09-28 AT AT01616/69A patent/AT281032B/en not_active IP Right Cessation
- 1967-09-28 AT AT01615/69A patent/AT281031B/en not_active IP Right Cessation
- 1967-09-28 NL NL6713219A patent/NL6713219A/xx unknown
- 1967-09-28 SE SE7001669A patent/SE388759B/en unknown
- 1967-09-28 SE SE13325/67A patent/SE342042B/xx unknown
- 1967-09-28 AT AT880867A patent/AT281030B/en not_active IP Right Cessation
- 1967-09-28 BE BE704458D patent/BE704458A/xx unknown
- 1967-09-28 DK DK482067AA patent/DK137492B/en unknown
- 1967-09-28 AT AT162069A patent/AT288841B/en not_active IP Right Cessation
- 1967-09-29 JP JP42062612A patent/JPS4827317B1/ja active Pending
- 1967-09-29 CS CS692767A patent/CS158209B2/cs unknown
-
1971
- 1971-09-23 JP JP46073946A patent/JPS4918205B1/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002052949A1 (en) * | 2001-01-08 | 2002-07-11 | Gormar Marketing Limited | Autoinducer compounds and their uses |
| AU2002219348B2 (en) * | 2001-01-08 | 2006-11-16 | Pathway Intermediates Ltd | Autoinducer compounds and their uses |
| US7651699B2 (en) | 2001-01-08 | 2010-01-26 | Pathway Intermediates Limited | Autoinducer compounds and their uses |
Also Published As
| Publication number | Publication date |
|---|---|
| DK137492B (en) | 1978-03-13 |
| DE1670464A1 (en) | 1971-02-11 |
| AT281031B (en) | 1970-05-25 |
| AT281030B (en) | 1970-05-11 |
| CS158209B2 (en) | 1974-10-15 |
| GB1205639A (en) | 1970-09-16 |
| JPS4827317B1 (en) | 1973-08-21 |
| SE388759B (en) | 1976-10-18 |
| DK137492C (en) | 1978-10-02 |
| AT281032B (en) | 1970-05-25 |
| SE342042B (en) | 1972-01-24 |
| FR1578721A (en) | 1969-08-22 |
| CH538476A (en) | 1973-06-30 |
| JPS4918205B1 (en) | 1974-05-08 |
| AT288841B (en) | 1971-03-25 |
| CH529136A (en) | 1972-10-15 |
| NL6713219A (en) | 1968-04-01 |
| BE704458A (en) | 1968-03-28 |
| FI48733B (en) | 1974-09-02 |
| CH519304A (en) | 1972-02-29 |
| IL28656A (en) | 1971-11-29 |
| FI48733C (en) | 1974-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |