CS740088A2 - Method of 1-tertiary alkylsubstituted naphthyridine and quinoline carboxylic acids preparation - Google Patents
Method of 1-tertiary alkylsubstituted naphthyridine and quinoline carboxylic acids preparationInfo
- Publication number
- CS740088A2 CS740088A2 CS887400A CS740088A CS740088A2 CS 740088 A2 CS740088 A2 CS 740088A2 CS 887400 A CS887400 A CS 887400A CS 740088 A CS740088 A CS 740088A CS 740088 A2 CS740088 A2 CS 740088A2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- oxo
- naphthyridine
- dimethylethyl
- opt
- dihydro
- Prior art date
Links
- 150000005054 naphthyridines Chemical class 0.000 title 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- CTXPWRRGJDHGNC-UHFFFAOYSA-N 1-tert-butyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C1=C2N(C(C)(C)C)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 CTXPWRRGJDHGNC-UHFFFAOYSA-N 0.000 abstract 1
- GNGUWCPRUDOETC-UHFFFAOYSA-N 1-tert-butyl-6-fluoro-7-(8-methyl-3,8-diazabicyclo[3.2.1]octan-3-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound CC(C)(C)N1C=C(C(O)=O)C(=O)C(C=C2F)=C1C=C2N(C1)CC2CCC1N2C GNGUWCPRUDOETC-UHFFFAOYSA-N 0.000 abstract 1
- IKFOCZDQWAIDRX-UHFFFAOYSA-N 3H-1,8-naphthyridin-4-one 4-oxo-3H-quinoline-3-carboxylic acid Chemical compound C1=CC=C2C(=O)CC=NC2=N1.C1=CC=C2C(=O)C(C(=O)O)C=NC2=C1 IKFOCZDQWAIDRX-UHFFFAOYSA-N 0.000 abstract 1
- NXKOWQUWRFWFDS-NOZJJQNGSA-N 7-[(3s,4r)-3-amino-4-methylpyrrolidin-1-yl]-1-tert-butyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C1[C@@H](N)[C@H](C)CN1C(C(=C1)F)=NC2=C1C(=O)C(C(O)=O)=CN2C(C)(C)C NXKOWQUWRFWFDS-NOZJJQNGSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 229910003204 NH2 Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 abstract 1
- -1 trifluoroacetylamino Chemical group 0.000 abstract 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
4-Oxo-naphthyridine- and 4-oxo-quinoline-3- carboxylic acid derivs. of formula (I) and pharmaceutically acceptable acid addn. and base salts are new. In (I), R1=tert. alkyl from tBu, -C(Me)2Et, -C(Ph)Me2, -CMe=CH2 and gps. of formulae (a)-(d), all opt. contg. 1-3 halogens; R=H or Me; X=F, Cl, Br, CF3 or CCl3; Y=CH, CF, CCl, CBr or N; W=NR2, S or O; R2=H, 1-6C alkyl (opt. substd. by 1-3 OH, F, Cl, NH2, alkylamino, trifluoroacetylamino or phenyl gps.), 3-6C cycloalkyl or 3-6C cycloalkenyl; A, B, C, D=H, 1-4C alkyl (opt. substd. as above), NH2, OH, F, Cl or phenyl; n=0, 1, 2 or 3; and when N(R2)2 is present and is not NH2, then R2=Me or Et; provided that when R1= (b), then Z is not gp. (f) where one R2 is H and A-D=H. - Among pref. cpds. the following are typical; 1-(1,1-dimethylethyl)-1,4- dihydro-6-fluoro-7 piperazinyl-4-oxo-3-quinoline carboxylic acid, methanesulphonate (IA); 7-(8-methyl-3,8-diazabicyclo (3.2.1)octan-3-yl)-1- (1,1-dimethylethyl)-1,4 dihydro-6-fluoro-4-oxo-3- quinolinecarboxylic acid, hydrochloride; and 7-(trans-3-amino-4- methylpyrrolidin-1-yl) -1-(1,1-dimethylethyl)- 1,4-dihydro-6-fluoro-4 oxo-1,8-naphthyridine-3- carboxylic acid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91675286A | 1986-10-08 | 1986-10-08 | |
| CS877295A CS270597B2 (en) | 1986-10-08 | 1987-10-08 | Method of tertiary alkylsubstituted naphthyridine and quinoline carboxylic acids production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS740088A2 true CS740088A2 (en) | 1989-11-14 |
| CS270598B2 CS270598B2 (en) | 1990-07-12 |
Family
ID=25746476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS887400A CS270598B2 (en) | 1986-10-08 | 1988-11-10 | Method of 1-tertiary alkylsubstituted naphthyridine and quinoline carboxylic acids preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS270598B2 (en) |
-
1988
- 1988-11-10 CS CS887400A patent/CS270598B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS270598B2 (en) | 1990-07-12 |
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