Isoxepac
2-(11-Oxo-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetic acid · Olapatadine · Olopatadine Related CoMpound C · 6,11-DIHYDRO-11-OXO-DIBENZ[B,E]OXEPIN-2-ACETIC ACID · 6,11-Dihydro-11-oxodibenzo[b,e]oxepin-2-acetic Acid · hp549 · artil · ND4-B2
Identifikatoren & physikalische Daten
| CAS No. | 55453-87-7 |
|---|---|
| Summenformel | C16H12O4 |
| Durchschnittliche Molmasse | 268,26 g/mol |
| Monoisotopische Masse | 268,07355886 g/mol |
| SMILES | O=C(O)Cc1ccc2c(c1)C(=O)c1ccccc1CO2 |
| InChIKey | QFGMXJOBTNZHEL-UHFFFAOYSA-N |
| PubChem CID | 41448 |
| ChEMBL | CHEMBL33211 |
| ChEBI | CHEBI:135102 |
| EC No. | 611-268-9 |
| DTXSID | DTXSID8057772 |
Chemische & physikalische Eigenschaften
| XLogP | 2,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 63,6 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 20 |
| Formalladung | 0 |
| Komplexität | 392 |
| Schmelzpunkt | 130-132°C |
| Siedepunkt | 528.2±50.0 °C(Predicted) |
| Dichte | 1.39 g/cm3 |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Löslichkeit | soluble in Methanol |
| pKa (Säurekonstante) | 4.24±0.10(Predicted) |
| Aggregatzustand | Solid |
| Farbe | White to Light yellow to Light orange |
| Merck | 14,5237 |
| Hauptanwendungen | pharmaceutical (small molecule) |
| InChI | InChI=1S/C16H12O4/c17-15(18)8-10-5-6-14-13(7-10)16(19)12-4-2-1-3-11(12)9-20-14/h1-7H,8-9H2,(H,17,18) |
| InChIKey | QFGMXJOBTNZHEL-UHFFFAOYSA-N |
| SMILES | O1CC2=CC=CC=C2C(=O)C2=CC(CC(O)=O)=CC=C12 |
| CAS Datenbank | 55453-87-7(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (85.7%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P260, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 7 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (85.7%) |
| Wassergefährdungsklasse (WGK) | WGK 3 |
| UN-Transportnummer | UN 2811 6.1 / PGIII |
| Zollcode | 2932996560 |
| RTECS-Nr. | HQ4110000 |
| R-Sätze (R) | 25-62 |
| Toxizität | LD50 orally in rats: 199 mg/kg (Ueno) |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 36/37-45 |
| Gefahrenklasse | 6.1Acute Tox. 3 OralRepr. 2STOT RE 1 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Verwenden
Isoxepac is a non-steroidal anti-inflammatory with analgesic and antipyretic activity. It is more slowly absorbed and eliminated in the rat and rabbit after oral dosing than in the dog, rhesus monkey and man.It can be used to treat allergic rhinitis, urticaria, and skin diseases with itching symptoms.
Herstellung & Synthese
synthetische
Isoxic acid is an important intermediate in the synthesis of the new preferred anti-allergic drug, olopatadine hydrochloride, preparation method of isoxepac:(1) condensation: prepare p-hydroxyphenylaceticacid 8-12 part, phthalide 6-12 part, sodium methylate 8-12 part by weight; Dissolve with DMAC and to add said sodium methylate behind said p-hydroxyphenylaceticacid and the phthalide; Be that 0.1-10Pa is heated to 80-170 ℃ of reaction 3-10h at pressure then; Regulate the pH value to 1-5,4-(2-carboxyl benzyloxy) toluylic acid is separated out in crystallization;(2) cyclization: with Glacial acetic acid min. 99.5 dissolving step (1) gained 4-(2-carboxyl benzyloxy) toluylic acid, adding 3-52 weight part polyphosphoric acid again, is that 0.1-10Pa is heated to 30-100 ℃ of reaction 3-12h at pressure, and crystallisation by cooling gets the Isoxepac bullion then;(3) purify: behind the said Isoxepac bullion of acetic acid ethyl dissolution, refining decolouring gets the Isoxepac product.https://patents.google.com/patent/CN102838582A/en