FI91749C - Menetelmä kinoliini-karboksyylihappojohdannaisten valmistamiseksi - Google Patents
Menetelmä kinoliini-karboksyylihappojohdannaisten valmistamiseksi Download PDFInfo
- Publication number
- FI91749C FI91749C FI882326A FI882326A FI91749C FI 91749 C FI91749 C FI 91749C FI 882326 A FI882326 A FI 882326A FI 882326 A FI882326 A FI 882326A FI 91749 C FI91749 C FI 91749C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- carboxylic acid
- acid
- compound
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 7
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 25
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 239000000047 product Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000022244 formylation Effects 0.000 description 4
- 238000006170 formylation reaction Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NIBFJPXGNVPNHK-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-4-carbaldehyde Chemical group C1=CC(C=O)=C2OC(F)(F)OC2=C1 NIBFJPXGNVPNHK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- -1 formylpiperazine quinol compound Chemical class 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- WNNSMMJBBOPPOT-UHFFFAOYSA-N 7-chloro-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(Cl)C=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 WNNSMMJBBOPPOT-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KCXCSXLUYCTARV-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(4-formylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCN(CC3)C=O)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 KCXCSXLUYCTARV-UHFFFAOYSA-N 0.000 description 1
- NPILVNLCZWJDLC-UHFFFAOYSA-N 4-oxo-1-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=CC=CC=C2C(=O)C(C(=O)O)=CN1N1CCNCC1 NPILVNLCZWJDLC-UHFFFAOYSA-N 0.000 description 1
- LXBOHKNFMYPYOJ-UHFFFAOYSA-N 6-fluoro-1-(methylamino)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C1=C2N(NC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 LXBOHKNFMYPYOJ-UHFFFAOYSA-N 0.000 description 1
- ISPVACVJFUIDPD-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ISPVACVJFUIDPD-UHFFFAOYSA-N 0.000 description 1
- RCNJBEXSAWUACU-UHFFFAOYSA-N 7-chloro-6-fluoro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(Cl)C=C2N(NC)C=C(C(O)=O)C(=O)C2=C1 RCNJBEXSAWUACU-UHFFFAOYSA-N 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- LEBMVNWAZSHDSU-UHFFFAOYSA-N CNN1C=C(C(C2=CC(=C(C=C12)N1CCN(CC1)C=O)F)=O)C(=O)O Chemical compound CNN1C=C(C(C2=CC(=C(C=C12)N1CCN(CC1)C=O)F)=O)C(=O)O LEBMVNWAZSHDSU-UHFFFAOYSA-N 0.000 description 1
- BFGDJPQDLMOZQQ-UHFFFAOYSA-N N-Formylnorfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C=O)CC1 BFGDJPQDLMOZQQ-UHFFFAOYSA-N 0.000 description 1
- 241000606856 Pasteurella multocida Species 0.000 description 1
- 241001138501 Salmonella enterica Species 0.000 description 1
- 241000607760 Shigella sonnei Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940115939 shigella sonnei Drugs 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- C07D215/48—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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU864292A HU196987B (en) | 1986-10-15 | 1986-10-15 | Process for producing quinoline-carboxylic acid derivatives |
| HU429286 | 1986-10-15 | ||
| HU429287 | 1987-10-01 | ||
| HU429287 | 1987-10-01 | ||
| HU8700044 | 1987-10-14 | ||
| PCT/HU1987/000044 WO1988002748A1 (en) | 1986-10-15 | 1987-10-14 | Process for the preparation of quinoline-carboxylic acid derivatives |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI882326A0 FI882326A0 (fi) | 1988-05-18 |
| FI882326A7 FI882326A7 (fi) | 1988-05-18 |
| FI91749B FI91749B (fi) | 1994-04-29 |
| FI91749C true FI91749C (fi) | 1994-08-10 |
Family
ID=26317755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI882326A FI91749C (fi) | 1986-10-15 | 1988-05-18 | Menetelmä kinoliini-karboksyylihappojohdannaisten valmistamiseksi |
Country Status (7)
| Country | Link |
|---|---|
| KR (1) | KR880701712A (cs) |
| CA (1) | CA1312603C (cs) |
| CS (1) | CS269995B2 (cs) |
| DK (1) | DK322888A (cs) |
| ES (1) | ES2005432A6 (cs) |
| FI (1) | FI91749C (cs) |
| NO (1) | NO169389C (cs) |
-
1987
- 1987-10-14 CA CA000549293A patent/CA1312603C/en not_active Expired - Fee Related
- 1987-10-15 CS CS877469A patent/CS269995B2/cs unknown
- 1987-10-15 ES ES8703122A patent/ES2005432A6/es not_active Expired
-
1988
- 1988-05-18 FI FI882326A patent/FI91749C/fi not_active IP Right Cessation
- 1988-06-06 NO NO882493A patent/NO169389C/no unknown
- 1988-06-09 KR KR1019880700653A patent/KR880701712A/ko not_active Ceased
- 1988-06-14 DK DK322888A patent/DK322888A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO169389C (no) | 1992-06-17 |
| FI882326A0 (fi) | 1988-05-18 |
| FI882326A7 (fi) | 1988-05-18 |
| NO882493D0 (no) | 1988-06-06 |
| FI91749B (fi) | 1994-04-29 |
| KR880701712A (ko) | 1988-11-04 |
| NO882493L (no) | 1988-06-06 |
| DK322888D0 (da) | 1988-06-14 |
| CA1312603C (en) | 1993-01-12 |
| CS746987A2 (en) | 1989-09-12 |
| DK322888A (da) | 1988-06-14 |
| CS269995B2 (en) | 1990-05-14 |
| NO169389B (no) | 1992-03-09 |
| ES2005432A6 (es) | 1989-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: CHINOIN GYOGYSZER ES VEGYESZETI TERMEKEK GYARA RT. |