JPS621951B2 - - Google Patents
Info
- Publication number
- JPS621951B2 JPS621951B2 JP721576A JP721576A JPS621951B2 JP S621951 B2 JPS621951 B2 JP S621951B2 JP 721576 A JP721576 A JP 721576A JP 721576 A JP721576 A JP 721576A JP S621951 B2 JPS621951 B2 JP S621951B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- trifluoromethyl
- quinolinecarboxamide
- thiazolyl
- acid addition
- 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
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- CRWHDVMXBYUYKR-UHFFFAOYSA-N 7-chloro-4-oxo-n-(1,3-thiazol-2-yl)-1h-quinoline-3-carboxamide Chemical compound C=1C(Cl)=CC=C(C2=O)C=1NC=C2C(=O)NC1=NC=CS1 CRWHDVMXBYUYKR-UHFFFAOYSA-N 0.000 claims description 4
- JWTYLQVSJNLMNU-UHFFFAOYSA-N 8-chloro-4-oxo-n-(1,3-thiazol-2-yl)-1h-quinoline-3-carboxamide Chemical compound ClC1=CC=CC(C2=O)=C1NC=C2C(=O)NC1=NC=CS1 JWTYLQVSJNLMNU-UHFFFAOYSA-N 0.000 claims description 4
- -1 N-[2-pyridinyl]-3-quinolinecarboxamide Chemical compound 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- KSFTWHMRYGAGTB-UHFFFAOYSA-N N-(1,3-thiazol-2-yl)quinoline-3-carboxamide Chemical compound N1=CC(=CC2=CC=CC=C12)C(=O)NC=1SC=CN1 KSFTWHMRYGAGTB-UHFFFAOYSA-N 0.000 claims description 3
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000000202 analgesic effect Effects 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 4
- UZWINQJCKNAAFE-UHFFFAOYSA-N 7-chloro-4-oxo-1h-quinoline-3-carbonyl chloride Chemical compound ClC1=CC=C2C(=O)C(C(=O)Cl)=CNC2=C1 UZWINQJCKNAAFE-UHFFFAOYSA-N 0.000 description 4
- IISJJIASHFVTDW-UHFFFAOYSA-N 8-chloro-4-oxo-1h-quinoline-3-carbonyl chloride Chemical compound C1=CC=C2C(=O)C(C(=O)Cl)=CNC2=C1Cl IISJJIASHFVTDW-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- OJXCWHCTIMXMND-UHFFFAOYSA-N 4-oxo-n-(1,3-thiazol-2-yl)-7-(trifluoromethyl)-1h-quinoline-3-carboxamide Chemical compound C1=NC2=CC(C(F)(F)F)=CC=C2C(O)=C1C(=O)NC1=NC=CS1 OJXCWHCTIMXMND-UHFFFAOYSA-N 0.000 description 3
- SUZLPICITRHWOF-UHFFFAOYSA-N 4-oxo-n-(1,3-thiazol-2-yl)-8-(trifluoromethyl)-1h-quinoline-3-carboxamide Chemical compound C1=NC2=C(C(F)(F)F)C=CC=C2C(O)=C1C(=O)NC1=NC=CS1 SUZLPICITRHWOF-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- QFBRTAZCGKXPJK-UHFFFAOYSA-N 4-chloro-6,7-dihydro-5h-cyclopenta[d]pyrimidine Chemical compound ClC1=NC=NC2=C1CCC2 QFBRTAZCGKXPJK-UHFFFAOYSA-N 0.000 description 2
- RUXWBOOVPAHUFB-UHFFFAOYSA-N 4-oxo-8-(trifluoromethyl)-1h-quinoline-3-carbonyl chloride Chemical compound N1C=C(C(Cl)=O)C(=O)C2=C1C(C(F)(F)F)=CC=C2 RUXWBOOVPAHUFB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 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
- OBRAOYCABNWDNA-UHFFFAOYSA-N n-(1,3-oxazol-2-yl)-4-oxo-8-(trifluoromethyl)-1h-quinoline-3-carboxamide Chemical compound C1=NC2=C(C(F)(F)F)C=CC=C2C(O)=C1C(=O)NC1=NC=CO1 OBRAOYCABNWDNA-UHFFFAOYSA-N 0.000 description 2
- JXVMDKANKRHYFL-UHFFFAOYSA-N n-methyl-4-oxo-n-(1,3-thiazol-2-yl)-8-(trifluoromethyl)-1h-quinoline-3-carboxamide Chemical compound C=1N=C2C(C(F)(F)F)=CC=CC2=C(O)C=1C(=O)N(C)C1=NC=CS1 JXVMDKANKRHYFL-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ACTKAGSPIFDCMF-UHFFFAOYSA-N 1,3-oxazol-2-amine Chemical compound NC1=NC=CO1 ACTKAGSPIFDCMF-UHFFFAOYSA-N 0.000 description 1
- AKZMUICDVDUPLC-UHFFFAOYSA-N 2-(1,3-thiazol-2-yl)quinoline-3-carboxamide Chemical compound S1C(=NC=C1)C1=NC2=CC=CC=C2C=C1C(=O)N AKZMUICDVDUPLC-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- LGOJPRTUKCSZLM-UHFFFAOYSA-N 4-oxo-7-(trifluoromethyl)-1h-quinoline-3-carbonyl chloride Chemical compound N1C=C(C(Cl)=O)C(=O)C=2C1=CC(C(F)(F)F)=CC=2 LGOJPRTUKCSZLM-UHFFFAOYSA-N 0.000 description 1
- GQZVPBYGGIQINZ-UHFFFAOYSA-N 4-oxo-8-(trifluoromethyl)-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C(=O)O)=CNC2=C1C(F)(F)F GQZVPBYGGIQINZ-UHFFFAOYSA-N 0.000 description 1
- YZFUAAJMHYXNRX-UHFFFAOYSA-N 4-oxo-n-pyridin-2-yl-8-(trifluoromethyl)-1h-quinoline-3-carboxamide Chemical compound C1=NC2=C(C(F)(F)F)C=CC=C2C(O)=C1C(=O)NC1=CC=CC=N1 YZFUAAJMHYXNRX-UHFFFAOYSA-N 0.000 description 1
- MQDCOKGAQYWIDE-UHFFFAOYSA-N 8-chloro-4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C(=O)O)=CNC2=C1Cl MQDCOKGAQYWIDE-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 241001465754 Metazoa Species 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MYTMXVHNEWBFAL-UHFFFAOYSA-L dipotassium;carbonate;hydrate Chemical compound O.[K+].[K+].[O-]C([O-])=O MYTMXVHNEWBFAL-UHFFFAOYSA-L 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 208000013465 muscle pain Diseases 0.000 description 1
- BUUDYQYASYIPBX-UHFFFAOYSA-N n-(1,3-thiazol-2-yl)-8-(trifluoromethyl)quinoline-3-carboxamide Chemical compound C=1N=C2C(C(F)(F)F)=CC=CC2=CC=1C(=O)NC1=NC=CS1 BUUDYQYASYIPBX-UHFFFAOYSA-N 0.000 description 1
- DWVCPSQPTSNMRX-UHFFFAOYSA-N n-methyl-1,3-thiazol-2-amine Chemical compound CNC1=NC=CS1 DWVCPSQPTSNMRX-UHFFFAOYSA-N 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 description 1
- HNUSZIQSLZBZTO-UHFFFAOYSA-N quinoline-3-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CN=C21 HNUSZIQSLZBZTO-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- BLTDCIWCFCUQCB-UHFFFAOYSA-N quionoline-3-carboxamide Natural products C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP721576A JPS5291876A (en) | 1976-01-27 | 1976-01-27 | Novel derivatives of 33quinolinecarboxylic acid and medicine comprising same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP721576A JPS5291876A (en) | 1976-01-27 | 1976-01-27 | Novel derivatives of 33quinolinecarboxylic acid and medicine comprising same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5291876A JPS5291876A (en) | 1977-08-02 |
| JPS621951B2 true JPS621951B2 (enrdf_load_stackoverflow) | 1987-01-16 |
Family
ID=11659765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP721576A Granted JPS5291876A (en) | 1976-01-27 | 1976-01-27 | Novel derivatives of 33quinolinecarboxylic acid and medicine comprising same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5291876A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2443467A1 (fr) * | 1978-12-08 | 1980-07-04 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
| FR2509728A1 (fr) * | 1981-07-17 | 1983-01-21 | Roussel Uclaf | Nouveaux derives de la quinoleine, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
-
1976
- 1976-01-27 JP JP721576A patent/JPS5291876A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5291876A (en) | 1977-08-02 |
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