CA2831730A1 - A crystalline form of a salt of a morpholino sulfonyl indole derivative and a process for its preparation - Google Patents
A crystalline form of a salt of a morpholino sulfonyl indole derivative and a process for its preparation Download PDFInfo
- Publication number
- CA2831730A1 CA2831730A1 CA2831730A CA2831730A CA2831730A1 CA 2831730 A1 CA2831730 A1 CA 2831730A1 CA 2831730 A CA2831730 A CA 2831730A CA 2831730 A CA2831730 A CA 2831730A CA 2831730 A1 CA2831730 A1 CA 2831730A1
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- Prior art keywords
- compound
- cancer
- crystalline form
- solvent
- process according
- 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.)
- Abandoned
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- 230000008569 process Effects 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 150000003839 salts Chemical class 0.000 title abstract description 10
- CZWPOIYWNZYKCD-UHFFFAOYSA-N 4-(1h-indol-2-ylsulfonyl)morpholine Chemical class C=1C2=CC=CC=C2NC=1S(=O)(=O)N1CCOCC1 CZWPOIYWNZYKCD-UHFFFAOYSA-N 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 225
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- 108010001127 Insulin Receptor Proteins 0.000 claims abstract description 35
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 71
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 59
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- 239000002904 solvent Substances 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 50
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 43
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 41
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 38
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 27
- 239000000243 solution Substances 0.000 claims description 27
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 24
- 229940011051 isopropyl acetate Drugs 0.000 claims description 24
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 24
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
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- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 19
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 16
- 230000001404 mediated effect Effects 0.000 claims description 16
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 230000008025 crystallization Effects 0.000 claims description 12
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 12
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- 239000002585 base Substances 0.000 claims description 11
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 claims description 11
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- 229940126062 Compound A Drugs 0.000 claims description 7
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 7
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 7
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- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
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- 235000010288 sodium nitrite Nutrition 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 5
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 3
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- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161477937P | 2011-04-21 | 2011-04-21 | |
| US61/477,937 | 2011-04-21 | ||
| PCT/IB2012/051967 WO2012143879A1 (en) | 2011-04-21 | 2012-04-19 | A crystalline form of a salt of a morpholino sulfonyl indole derivative and a process for its preparation |
Publications (1)
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|---|---|
| CA2831730A1 true CA2831730A1 (en) | 2012-10-26 |
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| CA2833009A Abandoned CA2833009A1 (en) | 2011-04-21 | 2012-04-19 | Insulin-like growth factor-1 receptor inhibitors |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| CA2833009A Abandoned CA2833009A1 (en) | 2011-04-21 | 2012-04-19 | Insulin-like growth factor-1 receptor inhibitors |
Country Status (9)
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|---|---|
| US (3) | US20140046059A1 (https=) |
| EP (2) | EP2699567A1 (https=) |
| JP (1) | JP2014514321A (https=) |
| CN (1) | CN103732592A (https=) |
| AU (2) | AU2012245971A1 (https=) |
| CA (2) | CA2831730A1 (https=) |
| IL (1) | IL228810A0 (https=) |
| IN (1) | IN2013MN02170A (https=) |
| WO (3) | WO2012143874A1 (https=) |
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| AU2012245971A1 (en) * | 2011-04-21 | 2013-10-17 | Piramal Enterprises Limited | A crystalline form of a salt of a morpholino sulfonyl indole derivative and a process for its preparation |
| WO2014002007A1 (en) * | 2012-06-26 | 2014-01-03 | Piramal Enterprises Limited | Method of predicting or monitoring response to igf-1r and ir inhibitors using biomarkers |
| MX359651B (es) | 2012-11-29 | 2018-10-05 | Chemocentryx Inc | Antagonistas de cxcr7. |
| WO2014177915A1 (en) | 2013-05-01 | 2014-11-06 | Piramal Enterprises Limited | Cancer combination therapy using imidazo[4,5-c]quinoline derivatives |
| CN104098498A (zh) * | 2014-07-30 | 2014-10-15 | 天津市斯芬克司药物研发有限公司 | 一种吲唑类化合物及其制备方法 |
| EP3219100A1 (en) | 2014-09-15 | 2017-09-20 | Dmitry Gorilovsky | A system comprising multiple digital cameras viewing a large scene |
| CN105218475A (zh) * | 2015-10-15 | 2016-01-06 | 湖南华腾制药有限公司 | 1,2-吗啉盐酸盐的合成方法 |
| AU2018386327B2 (en) | 2017-12-15 | 2023-04-13 | Inthera Bioscience AG | 1 -(piperidinocarbonylmethyl)-2-oxopiperazine derivatives for treating cancer |
| MX2021006915A (es) | 2018-12-12 | 2021-08-24 | Chemocentryx Inc | Inhibidores de cxcr7 para el tratamiento de cancer. |
| AU2020337958A1 (en) | 2019-08-28 | 2022-03-17 | Horizon Therapeutics Ireland Dac | Methods for the treatment of thyroid eye disease |
| CN113149941A (zh) * | 2020-01-22 | 2021-07-23 | 中国科学院上海药物研究所 | 醚类化合物及其在防治糖尿病及代谢综合征中的药学用途 |
| EP4168014A1 (en) | 2020-06-19 | 2023-04-26 | Inthera Bioscience AG | Oxopiperazine derivatives for the treatment of cancer |
| AU2024287547A1 (en) | 2023-07-07 | 2026-01-22 | Viridian Therapeutics, Inc. | Methods of treating chronic thyroid eye disease |
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-
2012
- 2012-04-19 AU AU2012245971A patent/AU2012245971A1/en not_active Abandoned
- 2012-04-19 JP JP2014506536A patent/JP2014514321A/ja active Pending
- 2012-04-19 US US14/112,743 patent/US20140046059A1/en not_active Abandoned
- 2012-04-19 US US14/112,671 patent/US20140045847A1/en not_active Abandoned
- 2012-04-19 CN CN201280030276.3A patent/CN103732592A/zh active Pending
- 2012-04-19 US US14/113,166 patent/US20140045832A1/en not_active Abandoned
- 2012-04-19 IN IN2170MUN2013 patent/IN2013MN02170A/en unknown
- 2012-04-19 WO PCT/IB2012/051958 patent/WO2012143874A1/en not_active Ceased
- 2012-04-19 CA CA2831730A patent/CA2831730A1/en not_active Abandoned
- 2012-04-19 EP EP12718823.3A patent/EP2699567A1/en not_active Withdrawn
- 2012-04-19 WO PCT/US2012/034188 patent/WO2012145471A1/en not_active Ceased
- 2012-04-19 WO PCT/IB2012/051967 patent/WO2012143879A1/en not_active Ceased
- 2012-04-19 EP EP12723912.7A patent/EP2699568A1/en not_active Withdrawn
- 2012-04-19 CA CA2833009A patent/CA2833009A1/en not_active Abandoned
- 2012-04-19 AU AU2012245455A patent/AU2012245455A1/en not_active Abandoned
-
2013
- 2013-10-09 IL IL228810A patent/IL228810A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012143879A1 (en) | 2012-10-26 |
| CA2833009A1 (en) | 2012-10-26 |
| EP2699568A1 (en) | 2014-02-26 |
| AU2012245971A1 (en) | 2013-10-17 |
| WO2012143874A1 (en) | 2012-10-26 |
| EP2699567A1 (en) | 2014-02-26 |
| US20140045832A1 (en) | 2014-02-13 |
| US20140045847A1 (en) | 2014-02-13 |
| AU2012245455A8 (en) | 2013-11-07 |
| IL228810A0 (en) | 2013-12-31 |
| AU2012245971A8 (en) | 2013-11-07 |
| JP2014514321A (ja) | 2014-06-19 |
| CN103732592A (zh) | 2014-04-16 |
| WO2012145471A1 (en) | 2012-10-26 |
| US20140046059A1 (en) | 2014-02-13 |
| AU2012245455A1 (en) | 2013-10-31 |
| IN2013MN02170A (https=) | 2015-06-12 |
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