CH628892A5 - Procedimento per la preparazione di acidi chinolinici ad attivita antiinfiammatoria. - Google Patents

Procedimento per la preparazione di acidi chinolinici ad attivita antiinfiammatoria. Download PDF

Info

Publication number: CH628892A5
Authority: CH; Switzerland
Prior art keywords: formula; quinolin; compounds; process according; reaction
Prior art date: 1977-06-22

Application number

CH768277A

Other languages

English (en)

Italian (it)

Inventor

Giorgio Ferrari

Vittorio Vecchietti

Original Assignee

Simes

Priority date (The priority date 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 date listed.)

1977-06-22

Filing date

1977-06-22

Publication date

1982-03-31

1977-06-22 Application filed by Simes filed Critical Simes

1977-06-22 Priority to CH768277A priority Critical patent/CH628892A5/it

1978-05-26 Priority to IT23904/78A priority patent/IT1192259B/it

1978-06-21 Priority to JP7432078A priority patent/JPS549285A/ja

1978-06-21 Priority to FR7818625A priority patent/FR2395262A1/fr

1978-06-22 Priority to GB7827591A priority patent/GB2001959A/en

1978-06-22 Priority to BE188769A priority patent/BE868359A/fr

1978-06-22 Priority to DE19782827472 priority patent/DE2827472A1/de

1982-03-31 Publication of CH628892A5 publication Critical patent/CH628892A5/it

Links

238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 4
239000002253 acid Substances 0.000 title description 8
150000007513 acids Chemical class 0.000 title description 5
230000003110 anti-inflammatory effect Effects 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical group OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000001204 N-oxides Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
239000007800 oxidant agent Substances 0.000 claims 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
238000001640 fractional crystallisation Methods 0.000 claims 2
238000004440 column chromatography Methods 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
-1 magnesium stearate Chemical compound 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
229940093499 ethyl acetate Drugs 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
229910019213 POCl3 Inorganic materials 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
159000000011 group IA salts Chemical class 0.000 description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000000829 suppository Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
INOGLHRUEYDAHX-UHFFFAOYSA-N 1-chlorobenzotriazole Chemical compound C1=CC=C2N(Cl)N=NC2=C1 INOGLHRUEYDAHX-UHFFFAOYSA-N 0.000 description 1
QSXJUCAKCXXATL-UHFFFAOYSA-N 2-(2-chloroquinolin-6-yl)acetic acid Chemical compound N1=C(Cl)C=CC2=CC(CC(=O)O)=CC=C21 QSXJUCAKCXXATL-UHFFFAOYSA-N 0.000 description 1
MQTVBXYPMCIEFV-UHFFFAOYSA-N 2-(2-methoxyquinolin-6-yl)acetic acid Chemical compound C1=C(CC(O)=O)C=CC2=NC(OC)=CC=C21 MQTVBXYPMCIEFV-UHFFFAOYSA-N 0.000 description 1
UUUQZSRBYQMPCR-UHFFFAOYSA-N 2-(2-pyrazol-1-ylquinolin-6-yl)acetic acid Chemical compound N1(N=CC=C1)C1=NC2=CC=C(C=C2C=C1)CC(=O)O UUUQZSRBYQMPCR-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
244000144725 Amygdalus communis Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
RAHPCKCRRKFJNL-UHFFFAOYSA-N C1=CC2=C(C=CC(=N2)N3C=CN=C3)C=C1CC(=O)O Chemical compound C1=CC2=C(C=CC(=N2)N3C=CN=C3)C=C1CC(=O)O RAHPCKCRRKFJNL-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
208000009386 Experimental Arthritis Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
229910006124 SOCl2 Inorganic materials 0.000 description 1
238000005614 Skraup synthesis reaction Methods 0.000 description 1
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000001785 acacia senegal l. willd gum Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
235000020224 almond Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
229940025084 amphetamine Drugs 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000679 carrageenan Substances 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
229940113118 carrageenan Drugs 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
GPBLWJQFTVDYFO-UHFFFAOYSA-N ethyl 2-quinolin-6-ylacetate Chemical compound N1=CC=CC2=CC(CC(=O)OCC)=CC=C21 GPBLWJQFTVDYFO-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
229960000890 hydrocortisone Drugs 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
FSSVIYSWRLKICW-UHFFFAOYSA-N n-ethyl-n-phenylacetamide Chemical compound CCN(C(C)=O)C1=CC=CC=C1 FSSVIYSWRLKICW-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012439 solid excipient Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
230000009466 transformation Effects 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- C07D215/18—Halogen atoms or nitro radicals
- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C07D215/60—N-oxides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Rheumatology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)

CH768277A 1977-06-22 1977-06-22 Procedimento per la preparazione di acidi chinolinici ad attivita antiinfiammatoria. CH628892A5 (it)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
CH768277A CH628892A5 (it)	1977-06-22	1977-06-22	Procedimento per la preparazione di acidi chinolinici ad attivita antiinfiammatoria.
IT23904/78A IT1192259B (it)	1977-06-22	1978-05-26	Acidi chinolinici ad attivita' antiinfiammatoria e procedimento per la loro preparazione
JP7432078A JPS549285A (en)	1977-06-22	1978-06-21	Quinolinic acid having antiiinflammatory action and its preparation
FR7818625A FR2395262A1 (fr)	1977-06-22	1978-06-21	Nouveaux acides quinoleiniques utiles notamment comme antiinflammatoires et leur procede de preparation
GB7827591A GB2001959A (en)	1977-06-22	1978-06-22	Substituted quinolinic acids having anti-inflammatory activity, their preparation, and their use
BE188769A BE868359A (fr)	1977-06-22	1978-06-22	Nouveaux acides quinoleiniques utiles notamment comme anti-inflammatoires et leur procede de preparation
DE19782827472 DE2827472A1 (de)	1977-06-22	1978-06-22	Chinolinsaeuren mit anti-inflammatorischer aktivitaet und verfahren zu ihrer herstellung

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH768277A CH628892A5 (it)	1977-06-22	1977-06-22	Procedimento per la preparazione di acidi chinolinici ad attivita antiinfiammatoria.

Publications (1)

Publication Number	Publication Date
CH628892A5 true CH628892A5 (it)	1982-03-31

Family

ID=4328943

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH768277A CH628892A5 (it)	1977-06-22	1977-06-22	Procedimento per la preparazione di acidi chinolinici ad attivita antiinfiammatoria.

Country Status (7)

Country	Link
JP (1)	JPS549285A (fr)
BE (1)	BE868359A (fr)
CH (1)	CH628892A5 (fr)
DE (1)	DE2827472A1 (fr)
FR (1)	FR2395262A1 (fr)
GB (1)	GB2001959A (fr)
IT (1)	IT1192259B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS58116466A (ja) *	1981-12-29	1983-07-11	Nippon Zoki Pharmaceut Co Ltd	新規キノリル酢酸誘導体及び該化合物を含有する医薬組成物
DE3839332A1 (de) *	1988-11-22	1990-05-23	Bayer Ag	Verfahren zur herstellung von substituierten 2-chlorpyridinen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3991061A (en) *	1975-07-16	1976-11-09	G. D. Searle & Co.	Azanaphthaleneacetic acid derivatives

1977
- 1977-06-22 CH CH768277A patent/CH628892A5/it not_active IP Right Cessation
1978
- 1978-05-26 IT IT23904/78A patent/IT1192259B/it active
- 1978-06-21 FR FR7818625A patent/FR2395262A1/fr active Granted
- 1978-06-21 JP JP7432078A patent/JPS549285A/ja active Pending
- 1978-06-22 DE DE19782827472 patent/DE2827472A1/de not_active Withdrawn
- 1978-06-22 BE BE188769A patent/BE868359A/fr not_active IP Right Cessation
- 1978-06-22 GB GB7827591A patent/GB2001959A/en not_active Withdrawn

Also Published As

Publication number	Publication date
BE868359A (fr)	1978-10-16
DE2827472A1 (de)	1979-01-11
JPS549285A (en)	1979-01-24
GB2001959A (en)	1979-02-14
FR2395262B1 (fr)	1981-06-26
IT7823904A0 (it)	1978-05-26
FR2395262A1 (fr)	1979-01-19
IT1192259B (it)	1988-03-31

Legal Events

Date	Code	Title	Description
1985-02-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
US4192878A (en)	1980-03-11	Derivatives of thiazolidinecarboxylic acids and related acids
US4714762A (en)	1987-12-22	Antiarteriosclerotic substituted benzimidazol-2-yl-and 3H-imidazo[4,5-b]pyridin-2-yl-phenoxy-alkanoic acids and salts and esters thereof
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