GB1219721A - Pharmaceutical compositions - Google Patents
Pharmaceutical compositionsInfo
- Publication number
- GB1219721A GB1219721A GB8529/69A GB852969A GB1219721A GB 1219721 A GB1219721 A GB 1219721A GB 8529/69 A GB8529/69 A GB 8529/69A GB 852969 A GB852969 A GB 852969A GB 1219721 A GB1219721 A GB 1219721A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- methyl
- decyloxy
- carboxylate
- hydroxy
- 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
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 239000000543 intermediate Substances 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- CASBYSXOFBAEDS-UHFFFAOYSA-N 1-decoxy-2-nitrobenzene Chemical compound CCCCCCCCCCOC1=CC=CC=C1[N+]([O-])=O CASBYSXOFBAEDS-UHFFFAOYSA-N 0.000 abstract 1
- PVFWLRKOYPBTIB-UHFFFAOYSA-N 2-decoxy-N,N-diethyl-5-nitroaniline Chemical compound C(CCCCCCCCC)OC1=C(N(CC)CC)C=C(C=C1)[N+](=O)[O-] PVFWLRKOYPBTIB-UHFFFAOYSA-N 0.000 abstract 1
- FJFVPTKENBLYAC-UHFFFAOYSA-N 2-decoxy-N,N-diethylaniline Chemical compound C(CCCCCCCCC)OC1=C(N(CC)CC)C=CC=C1 FJFVPTKENBLYAC-UHFFFAOYSA-N 0.000 abstract 1
- JAKHLQNEMUMGKP-UHFFFAOYSA-N 3,4-diethylaniline Chemical compound CCC1=CC=C(N)C=C1CC JAKHLQNEMUMGKP-UHFFFAOYSA-N 0.000 abstract 1
- RGQMYMUHYKCPMO-UHFFFAOYSA-N 4-(2-propan-2-yloxypropyl)aniline Chemical compound CC(C)OC(C)CC1=CC=C(N)C=C1 RGQMYMUHYKCPMO-UHFFFAOYSA-N 0.000 abstract 1
- YJANSSSMZDZFKU-UHFFFAOYSA-N 4-bromo-1,2-diethylbenzene Chemical compound CCC1=CC=C(Br)C=C1CC YJANSSSMZDZFKU-UHFFFAOYSA-N 0.000 abstract 1
- SQKIEOHVIQZXNX-UHFFFAOYSA-N 4-decoxy-3-N,3-N-diethylbenzene-1,3-diamine Chemical compound C(C)N(C=1C=C(N)C=CC1OCCCCCCCCCC)CC SQKIEOHVIQZXNX-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- VZGBYOVWARGTNX-UHFFFAOYSA-N N-[4-(2-propan-2-yloxypropyl)phenyl]acetamide Chemical compound C(C)(C)OC(CC1=CC=C(C=C1)NC(C)=O)C VZGBYOVWARGTNX-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 abstract 1
- UDHGQKGSVIWMQC-UHFFFAOYSA-N dimethyl 2-(dimethoxymethyl)propanedioate Chemical compound COC(OC)C(C(=O)OC)C(=O)OC UDHGQKGSVIWMQC-UHFFFAOYSA-N 0.000 abstract 1
- ZJAJYXYKRRRCMK-UHFFFAOYSA-N dimethyl 2-(methoxymethyl)propanedioate Chemical compound COCC(C(=O)OC)C(=O)OC ZJAJYXYKRRRCMK-UHFFFAOYSA-N 0.000 abstract 1
- IZUIRUXCEZRABH-UHFFFAOYSA-N ethyl 6-decyl-7-(diethylamino)-4-oxo-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=C(C=C12)CCCCCCCCCC)N(CC)CC)C(=O)OCC IZUIRUXCEZRABH-UHFFFAOYSA-N 0.000 abstract 1
- QSNZUXZJCZHSQP-UHFFFAOYSA-N methyl 4-oxo-7-propan-2-yloxy-6-propyl-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=C(C=C12)CCC)OC(C)C)C(=O)OC QSNZUXZJCZHSQP-UHFFFAOYSA-N 0.000 abstract 1
- OBCCLVREHLEMJK-UHFFFAOYSA-N methyl 6-decoxy-7-(diethylamino)-4-oxo-1H-quinoline-3-carboxylate Chemical compound OC1=C(C=NC2=CC(=C(C=C12)OCCCCCCCCCC)N(CC)CC)C(=O)OC OBCCLVREHLEMJK-UHFFFAOYSA-N 0.000 abstract 1
- NMYCTBARPUAEQN-UHFFFAOYSA-N methyl 7-(diethylamino)-4-oxo-6-propyl-1h-quinoline-3-carboxylate Chemical compound N1C=C(C(=O)OC)C(=O)C2=C1C=C(N(CC)CC)C(CCC)=C2 NMYCTBARPUAEQN-UHFFFAOYSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- WEIMMECSAQVSGO-UHFFFAOYSA-N n-(3-hydroxy-4-propylphenyl)acetamide Chemical compound CCCC1=CC=C(NC(C)=O)C=C1O WEIMMECSAQVSGO-UHFFFAOYSA-N 0.000 abstract 1
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 abstract 1
- 150000003248 quinolines Chemical class 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 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)
- Quinoline Compounds (AREA)
Abstract
1,219,721. Quinoline derivatives; intermediates therefor. MERCK & CO. Inc. 17 Feb., 1969 [19 Feb., 1968; 9 Dec., 1968], No. 8529/69. Heading C2C. [Also in Division A5] Methyl 6 - decyloxy - 7 - diethylamino - 4- hydroxy - quinoline - 3 - carboxylate is prepared from dimethyl dimethoxymethylmalonate and 3 - diethylamino - 4 - decyloxy - aniline in turn prepared through the following intermediates: 2 - Decyloxy nitrobenzene; 2 - decyloxy - N,N- diethyl aniline; and 2 - decyloxy - 5 - nitro- N,N - diethyl aniline. Ethyl 6 - decyl - 7 - diethylamino - 4 - hydroxy - quinoline - 3 - carboxylate and the corresponding methyl ester are prepared similarly. Methyl 4 - hydroxy - 6,7 - diethyl quinoline- 3-carboxylate is prepared by cyclising methyl α- carboxymethoxy - # - (3,4 - diethylanilino)- acrylate prepared through the following intermediates: 4 - Bromo - 1,2 - diethyl benzene; and 3,4- diethyl aniline. Methyl 4 - hydroxy - 6 - propyl - 7 - isopropoxyquinoline-3-carboxylate is prepared from dimethylmethoxymethylmalonate and 2 - isopropoxy - 4 - amino - propyl benzene in turn prepared through the following intermediates: 2 - n - Propyl - 5 - acetamido phenol; and 2- isopropoxy - 4 - acetamido - n - propyl benzene. The preparation of the hydrochloride, sulphate and naphthalene-1,5-disulphonate of methyl 4- hydroxy - 6 - n - propyl - 7 - diethylaminoquinoline-3-carboxylate from the corresponding bases are also described.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70666868A | 1968-02-19 | 1968-02-19 | |
| US78245368A | 1968-12-09 | 1968-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1219721A true GB1219721A (en) | 1971-01-20 |
Family
ID=27107727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8529/69A Expired GB1219721A (en) | 1968-02-19 | 1969-02-17 | Pharmaceutical compositions |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1908262A1 (en) |
| FR (1) | FR2002194A1 (en) |
| GB (1) | GB1219721A (en) |
| IL (1) | IL31508A (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1007590A (en) * | 1962-04-09 | 1965-10-13 | Norwich Pharma Co | Lower alkyl esters of 6,7-di(lower)alkoxy-4-hydroxy-3-quinolinecarboxylic acid |
| US3478084A (en) * | 1965-12-22 | 1969-11-11 | Merck & Co Inc | Lower alkyl alpha-carboalkoxy-beta-(3,4-disubstituted anilino) acrylates |
| GB1168801A (en) * | 1966-05-13 | 1969-10-29 | May & Baker Ltd | Quinoline Derivatives |
-
1969
- 1969-01-28 IL IL31508A patent/IL31508A/en unknown
- 1969-02-17 GB GB8529/69A patent/GB1219721A/en not_active Expired
- 1969-02-19 DE DE19691908262 patent/DE1908262A1/en active Pending
- 1969-02-19 FR FR6904138A patent/FR2002194A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IL31508A0 (en) | 1969-04-30 |
| FR2002194A1 (en) | 1969-10-17 |
| DE1908262A1 (en) | 1969-09-11 |
| IL31508A (en) | 1972-02-29 |
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