GB1293626A - Substituted salicylic acid compounds - Google Patents
Substituted salicylic acid compoundsInfo
- Publication number
- GB1293626A GB1293626A GB2954370A GB2954370A GB1293626A GB 1293626 A GB1293626 A GB 1293626A GB 2954370 A GB2954370 A GB 2954370A GB 2954370 A GB2954370 A GB 2954370A GB 1293626 A GB1293626 A GB 1293626A
- Authority
- GB
- United Kingdom
- Prior art keywords
- halogen
- alkyl
- hydrogen
- fluorobenzoyl
- prepared
- 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
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 title abstract 3
- -1 hydroxy, amino Chemical group 0.000 abstract 11
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 abstract 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 2
- MFEOMRKVZPLQNY-UHFFFAOYSA-N (4-fluorophenyl)-(4-hydroxy-2-methylphenyl)methanone Chemical compound FC1=CC=C(C(=O)C=2C(=CC(=CC2)O)C)C=C1 MFEOMRKVZPLQNY-UHFFFAOYSA-N 0.000 abstract 1
- VWGWRNBIAWTWIB-UHFFFAOYSA-N (4-fluorophenyl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(F)C=C1 VWGWRNBIAWTWIB-UHFFFAOYSA-N 0.000 abstract 1
- DKBVXMGCXZZVTM-UHFFFAOYSA-N 1-methoxy-4-[(4-methylphenyl)methyl]benzene Chemical compound C1=CC(OC)=CC=C1CC1=CC=C(C)C=C1 DKBVXMGCXZZVTM-UHFFFAOYSA-N 0.000 abstract 1
- SLAGIIQLUQBLAF-UHFFFAOYSA-N 2-[(2-carboxy-3-hydroxyphenyl)methyl]-6-hydroxybenzoic acid Chemical class OC(=O)C1=C(O)C=CC=C1CC1=CC=CC(O)=C1C(O)=O SLAGIIQLUQBLAF-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- HLRVUOFDBXRZBI-UHFFFAOYSA-N 4-fluoro-4'-hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(F)C=C1 HLRVUOFDBXRZBI-UHFFFAOYSA-N 0.000 abstract 1
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 abstract 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004980 cyclopropylene group Chemical group 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 abstract 1
- 125000005358 mercaptoalkyl group Chemical group 0.000 abstract 1
- 125000006357 methylene carbonyl group Chemical group [H]C([H])([*:1])C([*:2])=O 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000002071 phenylalkoxy group Chemical group 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 abstract 1
- 229960004889 salicylic acid Drugs 0.000 abstract 1
- 150000003870 salicylic acids Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/105—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/19—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups having unsaturation outside the aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83660469A | 1969-06-25 | 1969-06-25 | |
| US3032070A | 1970-04-20 | 1970-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1293626A true GB1293626A (en) | 1972-10-18 |
Family
ID=26705907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2954370A Expired GB1293626A (en) | 1969-06-25 | 1970-06-18 | Substituted salicylic acid compounds |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS504653B1 (enrdf_load_stackoverflow) |
| CA (1) | CA940146A (enrdf_load_stackoverflow) |
| CH (1) | CH545265A (enrdf_load_stackoverflow) |
| DE (1) | DE2031224A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2053011A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1293626A (enrdf_load_stackoverflow) |
| NL (1) | NL7008627A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0276064A1 (en) * | 1987-01-12 | 1988-07-27 | Eli Lilly And Company | Anti-inflammatory agents |
| US4992576A (en) * | 1987-01-12 | 1991-02-12 | Eli Lilly And Company | Intermediates for leukotriene antagonists |
| US4996230A (en) * | 1990-02-16 | 1991-02-26 | Eli Lilly And Company | Leukotriene antagonists |
| US5171882A (en) * | 1987-01-12 | 1992-12-15 | Eli Lilly And Company | Leukotriene antagonists |
| US5235064A (en) * | 1987-01-12 | 1993-08-10 | Eli Lilly And Company | Leukotriene antagonists |
| US5683682A (en) * | 1989-11-15 | 1997-11-04 | Robertet S.A. | Derivatives of aromatic benzoates as inhibitors of esterase-producing micro-organisms |
| CN119019226A (zh) * | 2024-10-25 | 2024-11-26 | 山东第一医科大学(山东省医学科学院) | 一种光引发苯甲醚脱甲基的方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3635311A1 (de) * | 1986-10-17 | 1988-04-21 | Bayer Ag | Hydroxycarbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung in druck- oder waermeempfindlichen aufzeichnungsmaterialien |
| DE3635742A1 (de) * | 1986-10-21 | 1988-05-05 | Bayer Ag | Hydroxycarbonsaeurederivate und ihre verwendung in aufzeichnungsmaterialien |
| GB9214120D0 (en) * | 1991-07-25 | 1992-08-12 | Ici Plc | Therapeutic amides |
| GB9305295D0 (en) * | 1993-03-15 | 1993-05-05 | Zeneca Ltd | Therapeutic compounds |
| GB9310095D0 (en) * | 1993-05-17 | 1993-06-30 | Zeneca Ltd | Therapeutic compounds |
| DE69635254T2 (de) * | 1995-07-07 | 2006-07-13 | Astrazeneca Ab | Ortho-substituierte aromatische Verbindungen, die drei (Het)aryl-Ringe enthalten, deren Herstellung und deren Verwendung als Prostaglandin-E2-(PGE2)-Antagonisten |
| FR2762839B1 (fr) * | 1997-04-30 | 2001-05-11 | Oreal | Nouveaux derives de l'acide salicylique et leur utilisation dans une composition cosmetique et/ou dermatologique |
| JP4937435B2 (ja) * | 1998-11-05 | 2012-05-23 | 修一 広野 | 新規化合物およびその医薬用途 |
-
1970
- 1970-06-12 NL NL7008627A patent/NL7008627A/xx unknown
- 1970-06-15 CA CA085,563A patent/CA940146A/en not_active Expired
- 1970-06-18 GB GB2954370A patent/GB1293626A/en not_active Expired
- 1970-06-23 CH CH950170A patent/CH545265A/de not_active IP Right Cessation
- 1970-06-24 DE DE19702031224 patent/DE2031224A1/de active Pending
- 1970-06-24 FR FR7023324A patent/FR2053011A1/fr not_active Withdrawn
- 1970-06-25 JP JP5507370A patent/JPS504653B1/ja active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0276064A1 (en) * | 1987-01-12 | 1988-07-27 | Eli Lilly And Company | Anti-inflammatory agents |
| AU601541B2 (en) * | 1987-01-12 | 1990-09-13 | Eli Lilly And Company | Leukotriene antagonists |
| US4992576A (en) * | 1987-01-12 | 1991-02-12 | Eli Lilly And Company | Intermediates for leukotriene antagonists |
| US5171882A (en) * | 1987-01-12 | 1992-12-15 | Eli Lilly And Company | Leukotriene antagonists |
| US5235064A (en) * | 1987-01-12 | 1993-08-10 | Eli Lilly And Company | Leukotriene antagonists |
| US5683682A (en) * | 1989-11-15 | 1997-11-04 | Robertet S.A. | Derivatives of aromatic benzoates as inhibitors of esterase-producing micro-organisms |
| US4996230A (en) * | 1990-02-16 | 1991-02-26 | Eli Lilly And Company | Leukotriene antagonists |
| CN119019226A (zh) * | 2024-10-25 | 2024-11-26 | 山东第一医科大学(山东省医学科学院) | 一种光引发苯甲醚脱甲基的方法 |
| CN119019226B (zh) * | 2024-10-25 | 2025-01-07 | 山东第一医科大学(山东省医学科学院) | 一种光引发苯甲醚脱甲基的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7008627A (enrdf_load_stackoverflow) | 1970-12-29 |
| DE2031224A1 (de) | 1971-01-07 |
| FR2053011A1 (enrdf_load_stackoverflow) | 1971-04-16 |
| JPS504653B1 (enrdf_load_stackoverflow) | 1975-02-22 |
| CH545265A (de) | 1973-12-15 |
| CA940146A (en) | 1974-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |