DE2308732A1 - Neue 4,6-dioxo-pyridochinolin-2,8-dicarbonsaeure-derivate - Google Patents
Neue 4,6-dioxo-pyridochinolin-2,8-dicarbonsaeure-derivateInfo
- Publication number
- DE2308732A1 DE2308732A1 DE19732308732 DE2308732A DE2308732A1 DE 2308732 A1 DE2308732 A1 DE 2308732A1 DE 19732308732 DE19732308732 DE 19732308732 DE 2308732 A DE2308732 A DE 2308732A DE 2308732 A1 DE2308732 A1 DE 2308732A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- hydrogen
- radical
- dioxopyrido
- dicarboxylic acid
- 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.)
- Pending
Links
- -1 amine cation Chemical class 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 239000001257 hydrogen Substances 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 62
- 239000000243 solution Substances 0.000 claims description 61
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- 229910052783 alkali metal Inorganic materials 0.000 claims description 28
- 150000001340 alkali metals Chemical class 0.000 claims description 27
- 239000000460 chlorine Chemical group 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
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- 239000002184 metal Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
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- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 4
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- 229910001413 alkali metal ion Inorganic materials 0.000 claims 1
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- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
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- 238000001953 recrystallisation Methods 0.000 description 15
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 13
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 13
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- 238000000354 decomposition reaction Methods 0.000 description 11
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- 241001465754 Metazoa Species 0.000 description 10
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 10
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- 239000000443 aerosol Substances 0.000 description 9
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 9
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 8
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 208000006673 asthma Diseases 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
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- 239000013078 crystal Substances 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 229960004418 trolamine Drugs 0.000 description 6
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
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- 239000003380 propellant Substances 0.000 description 4
- WHSSOGYCQXMHCL-UHFFFAOYSA-N quinoline-2,8-dicarboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C(=O)O)=CC=C21 WHSSOGYCQXMHCL-UHFFFAOYSA-N 0.000 description 4
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- 230000001225 therapeutic effect Effects 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
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- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23003472A | 1972-02-28 | 1972-02-28 | |
| US23377272A | 1972-03-10 | 1972-03-10 | |
| US30397172A | 1972-11-06 | 1972-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2308732A1 true DE2308732A1 (de) | 1973-09-06 |
Family
ID=27398041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732308732 Pending DE2308732A1 (de) | 1972-02-28 | 1973-02-22 | Neue 4,6-dioxo-pyridochinolin-2,8-dicarbonsaeure-derivate |
Country Status (10)
| Country | Link |
|---|---|
| AR (1) | AR199285A1 (enrdf_load_stackoverflow) |
| CA (1) | CA984842A (enrdf_load_stackoverflow) |
| CH (1) | CH587847A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2308732A1 (enrdf_load_stackoverflow) |
| ES (1) | ES412088A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2181767B1 (enrdf_load_stackoverflow) |
| GB (2) | GB1427914A (enrdf_load_stackoverflow) |
| NL (1) | NL7302689A (enrdf_load_stackoverflow) |
| PH (1) | PH11020A (enrdf_load_stackoverflow) |
| SE (1) | SE397353B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4126617A (en) * | 1974-12-11 | 1978-11-21 | The Upjohn Company | DI-Tham salt of 10-cl,1,4,6,9 tetrahydro-5-methyl 4,6 dioxopyrido[3,2-g]quinoline-2,8-dicarboxylate |
| DE2560525C2 (enrdf_load_stackoverflow) * | 1975-12-19 | 1989-07-13 | C.H. Boehringer Sohn, 6507 Ingelheim, De |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE35639B1 (en) * | 1970-10-05 | 1976-04-14 | Ici Ltd | Pyridoquinoline derivatives |
-
1973
- 1973-02-01 CA CA162,631A patent/CA984842A/en not_active Expired
- 1973-02-02 GB GB3200075A patent/GB1427914A/en not_active Expired
- 1973-02-02 GB GB539773A patent/GB1425154A/en not_active Expired
- 1973-02-12 PH PH14338A patent/PH11020A/en unknown
- 1973-02-14 AR AR24658973A patent/AR199285A1/es active
- 1973-02-22 DE DE19732308732 patent/DE2308732A1/de active Pending
- 1973-02-26 CH CH277173A patent/CH587847A5/xx not_active IP Right Cessation
- 1973-02-26 SE SE7302647A patent/SE397353B/xx unknown
- 1973-02-27 ES ES412088A patent/ES412088A1/es not_active Expired
- 1973-02-27 NL NL7302689A patent/NL7302689A/xx not_active Application Discontinuation
- 1973-02-27 FR FR7306958A patent/FR2181767B1/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4126617A (en) * | 1974-12-11 | 1978-11-21 | The Upjohn Company | DI-Tham salt of 10-cl,1,4,6,9 tetrahydro-5-methyl 4,6 dioxopyrido[3,2-g]quinoline-2,8-dicarboxylate |
| DE2560525C2 (enrdf_load_stackoverflow) * | 1975-12-19 | 1989-07-13 | C.H. Boehringer Sohn, 6507 Ingelheim, De |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7302689A (enrdf_load_stackoverflow) | 1973-08-30 |
| GB1425154A (en) | 1976-02-18 |
| FR2181767B1 (enrdf_load_stackoverflow) | 1977-01-28 |
| ES412088A1 (es) | 1976-06-01 |
| AR199285A1 (es) | 1974-08-23 |
| SE397353B (sv) | 1977-10-31 |
| PH11020A (en) | 1977-10-25 |
| CA984842A (en) | 1976-03-02 |
| FR2181767A1 (enrdf_load_stackoverflow) | 1973-12-07 |
| CH587847A5 (enrdf_load_stackoverflow) | 1977-05-13 |
| GB1427914A (en) | 1976-03-10 |
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| OHA | Expiration of time for request for examination |