PL92578B1 - - Google Patents
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- Publication number
- PL92578B1 PL92578B1 PL1974187261A PL18726174A PL92578B1 PL 92578 B1 PL92578 B1 PL 92578B1 PL 1974187261 A PL1974187261 A PL 1974187261A PL 18726174 A PL18726174 A PL 18726174A PL 92578 B1 PL92578 B1 PL 92578B1
- Authority
- PL
- Poland
- Prior art keywords
- general formula
- compound
- compounds
- salt
- subjected
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
- -1 2-methylpyridinyl Chemical group 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- JHAYEQICABJSTP-UHFFFAOYSA-N decoquinate Chemical compound N1C=C(C(=O)OCC)C(=O)C2=C1C=C(OCC)C(OCCCCCCCCCC)=C2 JHAYEQICABJSTP-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- VCYQNCHWCSKOTO-UHFFFAOYSA-N 4-amino-2-ethoxyphenol Chemical compound CCOC1=CC(N)=CC=C1O VCYQNCHWCSKOTO-UHFFFAOYSA-N 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229960003683 amprolium Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229960001878 decoquinate Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- PJBQYZZKGNOKNJ-UHFFFAOYSA-M hydron;5-[(2-methylpyridin-1-ium-1-yl)methyl]-2-propylpyrimidin-4-amine;dichloride Chemical compound Cl.[Cl-].NC1=NC(CCC)=NC=C1C[N+]1=CC=CC=C1C PJBQYZZKGNOKNJ-UHFFFAOYSA-M 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000006187 pill Substances 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
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 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)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001403 HU167572B (en, 2012) | 1973-08-28 | 1973-08-28 | |
| HUCI001404 HU167573B (en, 2012) | 1973-08-28 | 1973-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL92578B1 true PL92578B1 (en, 2012) | 1977-04-30 |
Family
ID=26318396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1974187261A PL92578B1 (en, 2012) | 1973-08-28 | 1974-08-26 |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5082077A (en, 2012) |
| AT (1) | AT338789B (en, 2012) |
| CA (1) | CA1044239A (en, 2012) |
| CH (1) | CH615917A5 (en, 2012) |
| DD (1) | DD114077A1 (en, 2012) |
| DK (1) | DK141167B (en, 2012) |
| GB (1) | GB1467225A (en, 2012) |
| IN (1) | IN140826B (en, 2012) |
| NL (1) | NL7411324A (en, 2012) |
| NO (1) | NO145788C (en, 2012) |
| PL (1) | PL92578B1 (en, 2012) |
| SE (1) | SE406911B (en, 2012) |
| SU (1) | SU567402A3 (en, 2012) |
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 PL PL1974187261A patent/PL92578B1/pl unknown
- 1974-08-26 AT AT688374A patent/AT338789B/de not_active IP Right Cessation
- 1974-08-26 NL NL7411324A patent/NL7411324A/xx not_active Application Discontinuation
- 1974-08-27 NO NO743064A patent/NO145788C/no unknown
- 1974-08-27 GB GB3745174A patent/GB1467225A/en not_active Expired
- 1974-08-27 JP JP49098309A patent/JPS5082077A/ja active Pending
- 1974-08-27 DK DK454774AA patent/DK141167B/da not_active IP Right Cessation
- 1974-08-27 SU SU7402057994A patent/SU567402A3/ru active
- 1974-08-27 CH CH1168574A patent/CH615917A5/de not_active IP Right Cessation
- 1974-08-27 CA CA207,894A patent/CA1044239A/en not_active Expired
- 1974-08-28 IN IN1940/CAL/1974A patent/IN140826B/en unknown
- 1974-08-28 DD DD180757A patent/DD114077A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH615917A5 (en) | 1980-02-29 |
| CA1044239A (en) | 1978-12-12 |
| NO743064L (en, 2012) | 1975-03-24 |
| IN140826B (en, 2012) | 1976-12-25 |
| SE7410745L (en, 2012) | 1975-03-03 |
| DK454774A (en, 2012) | 1975-04-28 |
| SE406911B (sv) | 1979-03-05 |
| DK141167C (en, 2012) | 1980-06-23 |
| JPS5082077A (en, 2012) | 1975-07-03 |
| GB1467225A (en) | 1977-03-16 |
| NO145788B (no) | 1982-02-22 |
| DK141167B (da) | 1980-01-28 |
| ATA688374A (de) | 1977-01-15 |
| AT338789B (de) | 1977-09-12 |
| DD114077A1 (en, 2012) | 1975-07-12 |
| SU567402A3 (ru) | 1977-07-30 |
| NO145788C (no) | 1982-06-02 |
| NL7411324A (nl) | 1975-03-04 |
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