GB1152885A - Indazole-3-yl-Oxyalkanoic Acids and process for the preparation thereof - Google Patents
Indazole-3-yl-Oxyalkanoic Acids and process for the preparation thereofInfo
- Publication number
- GB1152885A GB1152885A GB2438467A GB2438467A GB1152885A GB 1152885 A GB1152885 A GB 1152885A GB 2438467 A GB2438467 A GB 2438467A GB 2438467 A GB2438467 A GB 2438467A GB 1152885 A GB1152885 A GB 1152885A
- Authority
- GB
- United Kingdom
- Prior art keywords
- indazole
- oxy
- reacting
- benzyl
- indazol
- 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
- 239000002253 acid Substances 0.000 title abstract 6
- 150000007513 acids Chemical class 0.000 title abstract 5
- -1 methoxy, nitro, amino Chemical group 0.000 abstract 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 4
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 150000002825 nitriles Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- VFBKPWOCFBXTQH-UHFFFAOYSA-N 2-(1-benzylindazol-3-yl)acetic acid Chemical compound C(C1=CC=CC=C1)N1N=C(C2=CC=CC=C12)CC(=O)O VFBKPWOCFBXTQH-UHFFFAOYSA-N 0.000 abstract 1
- APUOHIMFFPIDRF-UHFFFAOYSA-N 2-(n-nitrosoanilino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N(N=O)C1=CC=CC=C1 APUOHIMFFPIDRF-UHFFFAOYSA-N 0.000 abstract 1
- UBJSKHUOHFBLPD-UHFFFAOYSA-N 2-[1-[(3-chlorophenyl)methyl]-3-oxoindazol-2-yl]acetic acid Chemical compound ClC=1C=C(CN2N(C(C3=CC=CC=C23)=O)CC(=O)O)C=CC1 UBJSKHUOHFBLPD-UHFFFAOYSA-N 0.000 abstract 1
- VGUGHPUPUKPCGV-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]-3-oxoindazol-2-yl]acetic acid Chemical compound ClC1=CC=C(CN2N(C(C3=CC=CC=C23)=O)CC(=O)O)C=C1 VGUGHPUPUKPCGV-UHFFFAOYSA-N 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 abstract 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 abstract 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 abstract 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002366 halogen compounds Chemical class 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- SQNVFBHILRFQJY-UHFFFAOYSA-N n-(methylsulfamoyl)methanamine Chemical group CNS(=O)(=O)NC SQNVFBHILRFQJY-UHFFFAOYSA-N 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 230000009935 nitrosation Effects 0.000 abstract 1
- 238000007034 nitrosation reaction Methods 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 229960000380 propiolactone Drugs 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
Abstract
1,152,885. lndazol-3-yl-oxyalkanoic acids. AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO. 25 May, 1967 [29 Aug., 1966; 21 April, 1967], No. 24384/67. Heading C2C. Novel indazol-3-yl-oxyalkanoic acids of the general formula wherein X is hydrogen, chlorine, methoxy, nitro, amino or acetamino, R is hydrogen, phenyl or benzyl; phenyl and benzyl may be substituted with methyl, methoxy, halogen, trifluoromethyl or dimethylsulphamide and n is 1 or 2, and the non-toxic salts thereof with metals or organic bases and, when X=NH 2 the acid addition salts with organic and inorganic acids are prepared by reacting an alkali metal salt of the corresponding 3-oxy-indazole with a halogen compound of the formula Halogen-(CH 2 ) n -CR<SP>1</SP>, wherein R<SP>1</SP> is carboxy, carbethoxy, nitrile or carboxyamide, and where R<SP>1</SP> is other than carboxy, hydrolysing the resulting ester, nitrile or amide. Compounds in which n is 2 may also be prepared by reacting the sodium salt of the appropriate 3-oxy-indazole with propiolactone. In addition, benzyl and substituted benzyl derivatives may be obtained by reacting the corresponding unsubstituted indazole-3-ylalkanoic acids with the appropriate benzyl halide in an aqueous alkaline medium, and the 5 - nitro - 5 - amino- and 5 - acetamino - derivatives by nitrating the corresponding compound, wherein X is hydrogen, followed by reduction and acylation with acetic acid, if desired. Ethyl (1 - m - chlorobenzyl - indazol - 3 - one-2- yl) acetate and (1-p-chlorobenzyl-indazol-3-one- 2-yl) acetic acid are obtained as by-products by reacting an alkali metal salt of the appropriate 3-oxy-indazole with ethyl bromoacetal and bromoacetic acid respectively. (1-m-chlorobenzyl - indazol - 3 - one - 2 - yl) acetic acid is made by hydrolysing the above ester. The amide and nitrile of (1-benzyl-indazol- 3-yl) acetic acid and ethyl (1-m-chlorobenzylindazol-3-yl) acetate are prepared by reacting an alkali metal salt of the corresponding 3-oxyindazole with chloroacetamide, chloroacetonitrile and ethyl bromoacetate respectively. 1 - (2,6 - Dimethyl - 3 - dimethylsulphamoyl) phenyl-3-oxy-indazole is made by treating with zinc dust an acetic acid solution of N-(2,6- dimethyl - 3 - limethylsulphamoyl) phenyl - N- nitroso-anthranilic acid, resulting from the nitrosation of the corresponding substituted anthranilic acid. The sodium salt of 1-m-chlorobenzyl-3-oxyindazole is obtained by reacting 1-m-chlorobenzyl-3-oxy-indazole with sodium methoxide. The following starting materials are stated to be novel: 1-m-chlorophenyl-, 1-trifluoromethylphenyl-, 1-p-fluorophenyl-, and 1-mbromophenyl- 3 -oxy-indazoles. Therapeutic compositions, having anti-inflammatory activity contain the above novel indazole-3-yl-alkenoic acids or non-toxic salts thereof as the active ingredient.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1972366A IT1043762B (en) | 1966-08-29 | 1966-08-29 | INDAZOL 3 OXYACETIC ACIDS AND PROCESS FOR THEIR PREPARATION |
| IT2181066 | 1966-08-29 | ||
| IT1526767 | 1967-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1152885A true GB1152885A (en) | 1969-05-21 |
Family
ID=27272871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2438467A Expired GB1152885A (en) | 1966-08-29 | 1967-05-25 | Indazole-3-yl-Oxyalkanoic Acids and process for the preparation thereof |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH504442A (en) |
| DK (1) | DK115996B (en) |
| FR (1) | FR7174M (en) |
| GB (1) | GB1152885A (en) |
| NO (1) | NO118028B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19610882A1 (en) * | 1996-03-20 | 1997-09-25 | Dresden Arzneimittel | New 1,3,5-trisubstituted indazole derivatives with antiasthmatic, antiallergic, anti-inflammatory and immunomodulating effects, processes for their preparation and their use as medicines |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3664036D1 (en) * | 1985-02-12 | 1989-07-27 | Acraf | (1-phenylmethyl-5-hydroxy-1h-indazol-3-yl)-oxyacetic acid and salts thereof for use as a medicament, and pharmaceutical compositions containing them |
-
1967
- 1967-05-25 GB GB2438467A patent/GB1152885A/en not_active Expired
- 1967-05-26 DK DK276967A patent/DK115996B/en unknown
- 1967-05-30 NO NO16837867A patent/NO118028B/no unknown
- 1967-05-30 CH CH759167A patent/CH504442A/en not_active IP Right Cessation
- 1967-09-29 FR FR122803A patent/FR7174M/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19610882A1 (en) * | 1996-03-20 | 1997-09-25 | Dresden Arzneimittel | New 1,3,5-trisubstituted indazole derivatives with antiasthmatic, antiallergic, anti-inflammatory and immunomodulating effects, processes for their preparation and their use as medicines |
Also Published As
| Publication number | Publication date |
|---|---|
| CH504442A (en) | 1971-03-15 |
| FR7174M (en) | 1969-08-11 |
| DK115996B (en) | 1969-12-01 |
| NO118028B (en) | 1969-10-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE | Patent expired |