GB1380065A - 5-amino-isophthalic acid derivatives - Google Patents
5-amino-isophthalic acid derivativesInfo
- Publication number
- GB1380065A GB1380065A GB4629171A GB4629171A GB1380065A GB 1380065 A GB1380065 A GB 1380065A GB 4629171 A GB4629171 A GB 4629171A GB 4629171 A GB4629171 A GB 4629171A GB 1380065 A GB1380065 A GB 1380065A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diethyl
- anilino
- nitro
- amino
- benzylamino
- 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
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- ZIVMDGVNLSYXMB-UHFFFAOYSA-N 2-anilino-5-ethoxycarbonyl-3-nitrobenzoic acid Chemical compound N(C1=CC=CC=C1)C1=C(C=C(C(=O)OCC)C=C1C(=O)O)[N+](=O)[O-] ZIVMDGVNLSYXMB-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- BOEMWLSLLLDXOD-UHFFFAOYSA-N 3-nitro-2-phenyl-5-sulfanylcarbonylbenzoic acid Chemical class [N+](=O)([O-])C=1C(=C(C=C(C(=S)O)C1)C(=O)O)C1=CC=CC=C1 BOEMWLSLLLDXOD-UHFFFAOYSA-N 0.000 abstract 1
- UURIZAOKVAUQLS-UHFFFAOYSA-N 4-anilino-3-carbamoyl-5-nitrobenzoic acid Chemical compound N(C1=CC=CC=C1)C1=C(C=C(C(=O)O)C=C1C(N)=O)[N+](=O)[O-] UURIZAOKVAUQLS-UHFFFAOYSA-N 0.000 abstract 1
- SAWOKKQTYAWLPF-UHFFFAOYSA-N 4-anilino-5-nitrobenzene-1,3-dicarboxylic acid Chemical compound N(C1=CC=CC=C1)C1=C(C=C(C(=O)O)C=C1[N+](=O)[O-])C(=O)O SAWOKKQTYAWLPF-UHFFFAOYSA-N 0.000 abstract 1
- SHOLOUDRJYYCPP-UHFFFAOYSA-N 4-chloro-5-nitrobenzene-1,3-dicarboxylic acid Chemical compound ClC1=C(C=C(C(=O)O)C=C1[N+](=O)[O-])C(=O)O SHOLOUDRJYYCPP-UHFFFAOYSA-N 0.000 abstract 1
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical class NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 abstract 1
- BTNBVTZQYKXTOH-UHFFFAOYSA-N CC(C=C1)=CC=C1OC(C([N+]([O-])=O)=CC(C(O)=O)=C1)=C1C(O)=O Chemical class CC(C=C1)=CC=C1OC(C([N+]([O-])=O)=CC(C(O)=O)=C1)=C1C(O)=O BTNBVTZQYKXTOH-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- ISMPMSKDEONVNN-UHFFFAOYSA-N diethyl 4-anilino-5-nitrobenzene-1,3-dicarboxylate Chemical compound CCOC(=O)C1=CC(=C(NC2=CC=CC=C2)C(=C1)C(=O)OCC)[N+]([O-])=O ISMPMSKDEONVNN-UHFFFAOYSA-N 0.000 abstract 1
- YMIRYOHQZMNFNE-UHFFFAOYSA-N diethyl 5-(benzylamino)-4-(4-chlorophenyl)sulfanylbenzene-1,3-dicarboxylate Chemical compound C(C1=CC=CC=C1)NC=1C(=C(C=C(C(=O)OCC)C1)C(=O)OCC)SC1=CC=C(C=C1)Cl YMIRYOHQZMNFNE-UHFFFAOYSA-N 0.000 abstract 1
- RTWGEUOEQKHYAD-UHFFFAOYSA-N diethyl 5-(benzylamino)-4-phenoxybenzene-1,3-dicarboxylate Chemical compound C(C1=CC=CC=C1)NC=1C(=C(C=C(C(=O)OCC)C1)C(=O)OCC)OC1=CC=CC=C1 RTWGEUOEQKHYAD-UHFFFAOYSA-N 0.000 abstract 1
- NPJIYUOYXHYHIC-UHFFFAOYSA-N ethyl 1-(benzylamino)-5-ethoxycarbothioyl-2-phenylcyclohexa-2,4-diene-1-carboxylate Chemical compound C(C1=CC=CC=C1)NC1(CC(C(=S)OCC)=CC=C1C1=CC=CC=C1)C(=O)OCC NPJIYUOYXHYHIC-UHFFFAOYSA-N 0.000 abstract 1
- SAHDHWGGWWYQOO-UHFFFAOYSA-N ethyl 4-anilino-3-carbonochloridoyl-5-nitrobenzoate Chemical compound N(C1=CC=CC=C1)C1=C(C=C(C(=O)OCC)C=C1C(=O)Cl)[N+](=O)[O-] SAHDHWGGWWYQOO-UHFFFAOYSA-N 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- 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
- C07C205/59—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 the carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C205/60—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 the carbon skeleton being further substituted by singly-bound oxygen atoms in ortho-position to the carboxyl group, e.g. nitro-salicylic acids
-
- 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
- C07C205/58—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 the carbon skeleton being further substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Abstract
1380065 5-Aminoisophthalic acid derivatives LOVENS KEMISKE FABRIK PRODUKTIONSAKTIESELSKAB 28 Sept 1972 [5 Oct 1971 14 Dec 1971] 46291/71 Heading C2C [Also in Division A5] Novel therapeutic compounds (I) (including salts and esters thereof) in which X, is -O-, -S-, or -NH-; R 1 is hydrogen or an aliphatic radical with from one to four carbon atoms; R 2 and R 3 are hydrogen or a saturated or unsaturated, straight or branched optionally substituted aliphatic radical with from one to six carbon atoms, or an aryl- or heterocyclic-substituted aliphatic radical with from one to four carbon atoms; and R 4 is an unsubstituted or substituted phenyl radical; are made by standard methods. The invention also comprises novel-3-benzylamino-5-ethoxy-carbonyl - 4 - (phenory-, -phenylthio- and -pchlorophenylthio)-benzoic acids. Compounds (IV) and (V), where COOE signifies an ester or free carboxy group, are also prepared as well as 4-chloro-5-nitroisophthalic acid and its diethyl ester, diethyl 4 - anilino - 5 - nitroisophthalate, ethyl - 4- anilino - 5 - carboxy - 3 - nitrobenzoate and its potassium salt, ethyl 4-anilino-5-chlorocarbonyl-3- nitrobenzoate, 4 - anilino - 5 - carbamoyl - 3- nitrobenzoic acid, 4-anilino-5-nitro-isophthalic acid, ethyl 4-anilino-5-carboxy-3-nitrobenzoate, 5-amino- and 5-nitro-4-phenylthio-isophthalic acids, diethyl 3-benzylamino-4-phenylthioisophthalate, 4 - p - chlorophenylthio - 5 - amino and -nitro - isophthalic acids, diethyl 5 - benzylamino- 4-(p-chlorophenylthio)-isophthalate, diethyl 5- nitro and -amino-4-phenoxyisophthalates diethyl 5-benzylamino-4-phenoxyisophthalate and diethyl 5-amino- and 5-nitro-4-p-tolyloxyisophthalates
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE789679D BE789679A (en) | 1971-10-05 | NEW DERIVATIVES OF 5-AMINO ISOPHTHALIC ACID AND THEIR PREPARATION PROCEDURES | |
| GB4629171A GB1380065A (en) | 1971-10-05 | 1971-10-05 | 5-amino-isophthalic acid derivatives |
| IE1238/72A IE37392B1 (en) | 1971-10-05 | 1972-09-12 | 5-amino-isophthalic acid derivatives |
| ZA726390A ZA726390B (en) | 1971-10-05 | 1972-09-19 | New 5-aminoisophthauc acid(3-amino-5-carboxybenzoic acid),to salts and esters of these compounds and to methods for their preparation |
| AU47031/72A AU466298B2 (en) | 1971-10-05 | 1972-09-25 | Derivatives of 5-amino isophthalic acid and salts and esters thereof |
| CA152,555A CA1002964A (en) | 1971-10-05 | 1972-09-26 | Methods for producing new diuretics |
| NL7213059A NL7213059A (en) | 1971-10-05 | 1972-09-27 | |
| US292525A US3864385A (en) | 1971-10-05 | 1972-09-27 | New 5-Aminoisophthalic Acid Derivatives, Salts And Esters Thereof And Methods For Their Preparation |
| LU66227A LU66227A1 (en) | 1971-10-05 | 1972-10-03 | |
| FR7235179A FR2158208B1 (en) | 1971-10-05 | 1972-10-04 | |
| DE19722248596 DE2248596A1 (en) | 1971-10-05 | 1972-10-04 | NEW DERIVATIVES OF AMINOISOPHTALIC ACID |
| SE7212799A SE400551B (en) | 1971-10-05 | 1972-10-04 | PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE 3-AMINO-5-CARBAMYLBENZOIC ACID DERIVATIVES |
| JP47099744A JPS4844229A (en) | 1971-10-05 | 1972-10-04 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4629171A GB1380065A (en) | 1971-10-05 | 1971-10-05 | 5-amino-isophthalic acid derivatives |
| GB5810071 | 1971-12-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1380065A true GB1380065A (en) | 1975-01-08 |
Family
ID=26265784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4629171A Expired GB1380065A (en) | 1971-10-05 | 1971-10-05 | 5-amino-isophthalic acid derivatives |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3864385A (en) |
| JP (1) | JPS4844229A (en) |
| BE (1) | BE789679A (en) |
| CA (1) | CA1002964A (en) |
| DE (1) | DE2248596A1 (en) |
| FR (1) | FR2158208B1 (en) |
| GB (1) | GB1380065A (en) |
| IE (1) | IE37392B1 (en) |
| LU (1) | LU66227A1 (en) |
| NL (1) | NL7213059A (en) |
| SE (1) | SE400551B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4204970A (en) * | 1978-12-07 | 1980-05-27 | Standard Oil Company (Indiana) | Lubricant compositions containing alkylated aromatic amino acid antioxidants |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50102767A (en) * | 1974-01-22 | 1975-08-14 | ||
| JPS62192494A (en) * | 1986-02-20 | 1987-08-24 | Echiren Chem Kk | Hydraulic fluid composition for use in hydraulic brake of automobile |
| WO1990005525A1 (en) * | 1988-11-23 | 1990-05-31 | Pfizer Inc. | Quinuclidine derivatives as substance p antagonists |
| ATE284392T1 (en) * | 1998-11-03 | 2004-12-15 | Abbott Gmbh & Co Kg | SUBSTITUTED 2-PHENYLBENZIMIDAZOLES, THEIR PRODUCTION AND USE |
| WO2006110683A1 (en) * | 2005-04-11 | 2006-10-19 | Abbott Laboratories | 2-substituted-1h-benzimidazole-4-carboxamides are parp inhibitors |
| TWI375673B (en) * | 2005-04-11 | 2012-11-01 | Abbott Lab | 1h-benzimidazole-4-carboxamides substituted with a quaternary carbon at the 2-position are potent parp inhibitors |
| WO2007059230A2 (en) * | 2005-11-15 | 2007-05-24 | Abbott Laboratories | Substituted 1h-benzimidazole-4-carboxamides are potent parp inhibitors |
| US20070259937A1 (en) * | 2006-05-02 | 2007-11-08 | Giranda Vincent L | Substituted 1h-benzimidazole-4-carboxamides are potent parp inhibitors |
| US8067613B2 (en) * | 2007-07-16 | 2011-11-29 | Abbott Laboratories | Benzimidazole poly(ADP ribose)polymerase inhibitors |
| WO2010083199A1 (en) * | 2009-01-19 | 2010-07-22 | Abbott Laboratories | Benzthiazole inhibitors of poly(adp-ribose)polymerase |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1252959B (en) * | 1964-12-31 | 1967-10-26 | Bayer Ag | Acaricidal agents |
-
0
- BE BE789679D patent/BE789679A/en unknown
-
1971
- 1971-10-05 GB GB4629171A patent/GB1380065A/en not_active Expired
-
1972
- 1972-09-12 IE IE1238/72A patent/IE37392B1/en unknown
- 1972-09-26 CA CA152,555A patent/CA1002964A/en not_active Expired
- 1972-09-27 NL NL7213059A patent/NL7213059A/xx not_active Application Discontinuation
- 1972-09-27 US US292525A patent/US3864385A/en not_active Expired - Lifetime
- 1972-10-03 LU LU66227A patent/LU66227A1/xx unknown
- 1972-10-04 FR FR7235179A patent/FR2158208B1/fr not_active Expired
- 1972-10-04 DE DE19722248596 patent/DE2248596A1/en active Pending
- 1972-10-04 SE SE7212799A patent/SE400551B/en unknown
- 1972-10-04 JP JP47099744A patent/JPS4844229A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4204970A (en) * | 1978-12-07 | 1980-05-27 | Standard Oil Company (Indiana) | Lubricant compositions containing alkylated aromatic amino acid antioxidants |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2158208A1 (en) | 1973-06-15 |
| DE2248596A1 (en) | 1973-04-12 |
| IE37392B1 (en) | 1977-07-20 |
| BE789679A (en) | 1973-04-04 |
| CA1002964A (en) | 1977-01-04 |
| NL7213059A (en) | 1973-04-09 |
| FR2158208B1 (en) | 1975-08-08 |
| LU66227A1 (en) | 1973-01-23 |
| SE400551B (en) | 1978-04-03 |
| US3864385A (en) | 1975-02-04 |
| JPS4844229A (en) | 1973-06-26 |
| IE37392L (en) | 1973-04-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |