IP Library Granted Patent US 9,695,150
Granted Patent B2
US 9,695,150 · App. 15/350,014 · Granted Jul 4, 2017

Crystalline form of a substituted quinoline compound and pharmaceutical compositions thereof

Inventors: Ning Xi (Newbury Park, CA); Mingming Sun (Guangdong, CN)
Assignees: CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD.
C07D401/12A61K9/0053A61K9/48A61K31/436A61K31/4709A61K38/21A61K45/06C07B2200/13
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Quick Facts
Patent No.
US 9,695,150
App. No.
15/350,014
Granted
Jul 4, 2017
Kind
B2
Abstract

The present invention relates to a crystalline form of N-(3-fluoro-4-((7-(2-hydroxy-2-methylpropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide p-toluenesulfonate, the process for preparing the crystalline form thereof, and pharmaceutical compositions comprising the crystalline form thereof. This invention also relates to a method of using such a crystalline form in the treatment of hyperproliferative diseases in mammals, especially in humans.

Claims (10)

1. A crystalline form of a compound of formula (I):

wherein the crystalline form is form C having:

a) an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 7.20°, about 10.06°, about 17.40°, about 17.75°, about 18.65°, about 19.48° and about 20.13°; or

b) an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at 7.20°±0.2°, 10.06°±0.2°, 17.40°±0.2°, 17.75°±0.2°, 18.65°±0.2°, 19.48°±0.2° and 20.13°±0.2°.

2. The crystalline form of claim 1 having an X-ray powder diffraction pattern comprising peaks, in terms of 2θ, at about 7.20°, about 10.06°, about 14.96°, about 16.76, about 17.40°, about 17.75°, about 18.65°, about 19.48°, about 20.13°, about 20.90°, about 21.71°, about 22.69°, about 23.37°, about 24.40°, about 25.52°, about 26.29° and about 28.41°; or at 7.20°±0.2°, 10.06°±0.2°, 14.96±0.2°, 16.76±0.2°, 17.40°±0.2°, 17.75°±0.2°, 18.65°±0.2°, 19.48°±0.2°, 20.13°±0.2°, 20.90°±0.2°, 21.71°±0.2°, 22.69°±0.2°, 23.37°±0.2°, 24.40°±0.2°, 25.52°±0.2°,26.29°±0.2° and 28.41°±0.2°.

3. The crystalline form of claim 1 , wherein the X-ray powder diffraction pattern is substantially in accordance with that shown in FIG. 1 .

4. The crystalline form of claim 1 , wherein the crystalline form is substantially pure.

5. A pharmaceutical composition comprising the crystalline form of claim 1 and a pharmaceutically acceptable excipient, carrier, vehicle or a combination thereof.

6. The pharmaceutical composition of claim 5 further comprising a therapeutic agent.

7. The pharmaceutical composition of claim 6 , wherein the therapeutic agent is melphalan, cyclophosphamide, ifosfamide, busulfan, carmustine, lomustine, streptozocin, cisplatin, carboplatin, oxaliplatin, dacarbazine, temozolomide, procarbazine, methotrexate, fluorouracil, cytarabine, gemcitabine, mercaptopurine, fludarabine, vinblastine, vincristine, vinorelbine, paclitaxel, docetaxel, topotecan, irinotecan, etoposide, trabectedin, dactinomycin, doxorubicin, epirubicin, daunorubicin, mitoxantrone, bleomycin, mitomycin, ixabepilone, tamoxifen, flutamide, gonadorelin analogues, megestrol, prednisone, dexamethasone, methylprednisolone, thalidomide, interferon alfa, leucovorin, sirolimus, temsirolimus, everolimus, afatinib, alisertib, amuvatinib, apatinib, axitinib, bosutinib, bortezomib, brivanib, cediranib, cabozantinib, crenolanib, crizotinib, dabrafenib, dacomitinib, danusertib, dasatinib, dovitinib, erlotinib, foretinib, ganetespib, gefitinib, ibrutinib, icotinib, imatinib, iniparib, lapatinib, lenvatinib, linifanib, linsitinib, masitinib, momelotinib, neratinib, nilotinib, niraparib, oprozomib, olaparib, pazopanib, pegaptanib, pictilisib, ponatinib, quizartinib, radotinib, regorafenib, rigosertib, rucaparib, ruxolitinib, saracatinib, saridegib, sorafenib, sunitinib, tasocitinib, telatinib, tivantinib, tivozanib, tofacitinib, trametinib, vandetanib, veliparib, vemurafenib, vismodegib, volasertib, alemtuzumab, bevacizumab, brentuximabvedotin, catumaxomab, cetuximab, denosumab, gemtuzumab, ipilimumab, nimotuzumab, ofatumumab, panitumumab, ramucirumab, rituximab, tositumomab, trastuzumab, idelalisib, duvelisib, gilteritinib, buparlisib, taselisib, copanlisib, voxtalisib, pilaralisib, sonolisib, perifosine, alectinib, ibrutinib, pertuzumab, nintedanib, cobimetinib, temsirolimus, sirolimus, pixantrone or a combination thereof.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 4, 2021
From: CALITOR SCIENCES, LLC.
To: SUNSHINE LAKE PHARMA CO., LTD.
Reel/Frame 056177/0572 →
CORRECTIVE ASSIGNMENT TO CORRECT THE 15/961,688 PREVIOUSLY RECORDED ON REEL 052922 FRAME 0077. ASSIGNOR(S) HEREBY CONFIRMS THE THE ASSIGNMENT. Recorded Sep 29, 2020
From: NORTH & SOUTH BROTHER PHARMACY INVESTMENT COMPANY LIMITED; CALITOR SCIENCES, LLC
To: SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES LLC
Reel/Frame 053921/0538 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 12, 2020
From: NORTH & SOUTH BROTHER PHARMACY INVESTMENT COMPANY LIMITED; CALITOR SCIENCES, LLC
To: SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES LLC
Reel/Frame 052922/0077 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 21, 2019
From: SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC
To: NORTH & SOUTH BROTHER PHARMACY INVESTMENT COMPANY LIMITED; CALITOR SCIENCES, LLC
Reel/Frame 050776/0657 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 16, 2016
From: XI, NING; SUN, MINGMING
To: SUNSHINE LAKE PHARMA CO. LTD; CALITOR SCIENCES, LLC
Reel/Frame 040633/0960 →
Continuity (2)
Provisional Application 62255392 · Nov 14, 2015
Related Publication 20170137404A1 · May 18, 2017