Garenoxacin mesylate hydrate → Garenoxacin

HRID 1018543Notes

Reaction equation

HRID 1018543 reaction equation
O.CS(O)(=O)=O.[CH:7]1([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:24]4[CH:25]=[C:26]5[C:30](=[CH:31][CH:32]=4)[C@@H:29]([CH3:33])[NH:28][CH2:27]5)[C:18]=3[O:20][CH:21]([F:23])[F:22])[C:13](=[O:34])[C:12]([C:35]([OH:37])=[O:36])=[CH:11]2)[CH2:9][CH2:8]1.OC1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O>>[CH:7]1([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:24]4[CH:25]=[C:26]5[C:30](=[CH:31][CH:32]=4)[C@@H:29]([CH3:33])[NH:28][CH2:27]5)[C:18]=3[O:20][CH:21]([F:23])[F:22])[C:13](=[O:34])[C:12]([C:35]([OH:37])=[O:36])=[CH:11]2)[CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 157690Garenoxacin mesylate hydrateHCID 440995(+)-Lactose

Product 1

HCID 124093GarenoxacinYield 0%

Procedure

380.4 g of (R)-1-cyclopropyl-8-difluoromethoxy-7-(1-methyl-2,3-dihydro-1H-5-isoindolyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid methanesulfonate monohydrate, 83.1 g of lactose, 36 g of corn starch and 27 g of carboxymethyl starch sodium (Primojel, Matsutani Kagaku) are mixed, and the mixture is thereafter introduced into a kneader (small size bench kneader, Koike Tekko) and then kneaded while 180 g of a 6% aqueous hydroxypropyl cellulose solution (HPC-L, Nippon Soda) is gradually added. The kneaded product is subjected to size reduction by a power mill (PS-04S, Dalton, 2-mm herringbone screen) and then dried by blowing air at 40° C. overnight. After the drying, the product is subjected to size reduction by a power mill (20-mesh square screen), and thereafter, 2.7 g of magnesium stearate is added thereto and mixed therewith to prepare a powder for tableting. This powder is tableted by a rotary type tablet machine (HP-18, Hata Tekko) using a punch having a diameter of 7.5 mm so that the weight of one tablet becomes 180 mg to obtain tablets each containing 100 mg of (R)-1-cyclopropyl-8-difluoromethoxy-7-(1-methyl-2,3-dihydro-1H-5-isoindolyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (as free base). This tablet is subjected to film coating in an aqueous system by conventional procedure (4 mg of hydroxypropylmethyl cellulose (TC-5), 0.8 mg of Macrogol 6000, 0.4 mg of titanium oxide and 0.4 mg of talc per tablet) to obtain a film-coated tablet.

Workup

  1. additionthe mixture is thereafter introduced into a kneader (small size bench kneader, Koike Tekko)
  2. additionis gradually added
  3. customdried
  4. customat 40° C.
  5. customovernight
  6. addition2.7 g of magnesium stearate is added
  7. additionmixed
  8. customto prepare a powder for tableting

Sources & evidence

ORD record
ord-5fbe8df629ec45e88eaada7d90e42097
Source dataset
uspto-grants-2002_11
Patent number
US06482835B2

Reaction notes

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