KR20140003433A - 고체 형태의 3-(4-(아미노메틸)-1-(5-메틸-7h-피롤로[2,3-d]피리미딘-4-일)피페리딘-4-카르복사미도)페닐 디메틸카르바메이트 - Google Patents
고체 형태의 3-(4-(아미노메틸)-1-(5-메틸-7h-피롤로[2,3-d]피리미딘-4-일)피페리딘-4-카르복사미도)페닐 디메틸카르바메이트 Download PDFInfo
- Publication number
- KR20140003433A KR20140003433A KR1020137014386A KR20137014386A KR20140003433A KR 20140003433 A KR20140003433 A KR 20140003433A KR 1020137014386 A KR1020137014386 A KR 1020137014386A KR 20137014386 A KR20137014386 A KR 20137014386A KR 20140003433 A KR20140003433 A KR 20140003433A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- pyrrolo
- pyrimidin
- carboxamido
- aminomethyl
- 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.)
- Withdrawn
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- PWPNYABQEOGNNC-UHFFFAOYSA-N [3-[[4-(aminomethyl)-1-(5-methyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carbonyl]amino]phenyl] n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC=CC(NC(=O)C2(CN)CCN(CC2)C=2C=3C(C)=CNC=3N=CN=2)=C1 PWPNYABQEOGNNC-UHFFFAOYSA-N 0.000 title claims description 16
- 239000007787 solid Substances 0.000 title abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 38
- -1 4- (aminomethyl) -1- (5-methyl-7H-pyrrolo [2,3-d] pyrimidin-4-yl) piperidine-4-carboxamido Chemical group 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 18
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- 208000035475 disorder Diseases 0.000 claims description 11
- MYOHNZJKOAODMX-UHFFFAOYSA-N phenyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC=CC=C1 MYOHNZJKOAODMX-UHFFFAOYSA-N 0.000 claims description 11
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 6
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
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- SLEOAIKKFXPOEN-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)O.C1(=CC=CC=C1)OC(N(C)C)=O Chemical compound C(C1=CC=CC=C1)(=O)O.C1(=CC=CC=C1)OC(N(C)C)=O SLEOAIKKFXPOEN-UHFFFAOYSA-N 0.000 claims description 4
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- DWLVWMUCHSLGSU-UHFFFAOYSA-M n,n-dimethylcarbamate Chemical compound CN(C)C([O-])=O DWLVWMUCHSLGSU-UHFFFAOYSA-M 0.000 claims description 3
- YNSPNGPGESPBIO-UHFFFAOYSA-N phenyl N,N-dimethylcarbamate hydrochloride Chemical compound Cl.CN(C)C(=O)Oc1ccccc1 YNSPNGPGESPBIO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- UTZVRFPLSSHYGF-UHFFFAOYSA-N carboxy(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)C(O)=O UTZVRFPLSSHYGF-UHFFFAOYSA-N 0.000 claims 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- DBMKZUSRONMQDE-UHFFFAOYSA-N dimethylcarbamic acid;phosphoric acid Chemical compound OP(O)(O)=O.CN(C)C(O)=O DBMKZUSRONMQDE-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 claims 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
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- KSECQYDNQYAZMQ-AWEZNQCLSA-N (2s)-n'-(3-bromophenyl)-n-cyano-2-methyl-4-(5-methyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboximidamide Chemical compound C([C@@H]1C)N(C=2C=3C(C)=CNC=3N=CN=2)CCN1C(=NC#N)NC1=CC=CC(Br)=C1 KSECQYDNQYAZMQ-AWEZNQCLSA-N 0.000 description 1
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 1
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 description 1
- JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Ophthalmology & Optometry (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41060210P | 2010-11-05 | 2010-11-05 | |
| US61/410,602 | 2010-11-05 | ||
| PCT/US2011/059086 WO2012061565A1 (en) | 2010-11-05 | 2011-11-03 | Solid forms of 3-(4-(aminomethyl)-1-(5-methyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140003433A true KR20140003433A (ko) | 2014-01-09 |
Family
ID=45002136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020137014386A Withdrawn KR20140003433A (ko) | 2010-11-05 | 2011-11-03 | 고체 형태의 3-(4-(아미노메틸)-1-(5-메틸-7h-피롤로[2,3-d]피리미딘-4-일)피페리딘-4-카르복사미도)페닐 디메틸카르바메이트 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8735408B2 (https=) |
| EP (1) | EP2635584A1 (https=) |
| JP (1) | JP2013541588A (https=) |
| KR (1) | KR20140003433A (https=) |
| CN (1) | CN103298815A (https=) |
| AR (1) | AR083756A1 (https=) |
| AU (1) | AU2011323371A1 (https=) |
| BR (1) | BR112013011094A2 (https=) |
| CA (1) | CA2817112A1 (https=) |
| IL (1) | IL225884A0 (https=) |
| MX (1) | MX2013004923A (https=) |
| RU (1) | RU2013125755A (https=) |
| SG (1) | SG190098A1 (https=) |
| TW (1) | TW201302754A (https=) |
| WO (1) | WO2012061565A1 (https=) |
| ZA (1) | ZA201302996B (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015150337A1 (en) | 2014-04-01 | 2015-10-08 | Amakem Nv | Lim kinase inhibitors |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI439457B (zh) * | 2007-09-28 | 2014-06-01 | Lexicon Pharmaceuticals Inc | （ｓ）－２－胺基－３－（４－（２－胺基－６－（（ｒ）－１－（４－氯－２－（３－甲基－１ｈ－吡唑－１－基）苯基）－２，２，２－三氟乙氧）－嘧啶－４－基）苯基）丙酸乙酯之固體形式與其使用方法 |
| US8193202B2 (en) | 2008-04-21 | 2012-06-05 | Lexicon Pharmaceuticals, Inc. | LIMK2 inhibitors, compositions comprising them, and methods of their use |
-
2011
- 2011-11-01 TW TW100139812A patent/TW201302754A/zh unknown
- 2011-11-03 BR BR112013011094A patent/BR112013011094A2/pt not_active IP Right Cessation
- 2011-11-03 WO PCT/US2011/059086 patent/WO2012061565A1/en not_active Ceased
- 2011-11-03 AU AU2011323371A patent/AU2011323371A1/en not_active Abandoned
- 2011-11-03 US US13/288,321 patent/US8735408B2/en active Active
- 2011-11-03 CA CA2817112A patent/CA2817112A1/en not_active Abandoned
- 2011-11-03 KR KR1020137014386A patent/KR20140003433A/ko not_active Withdrawn
- 2011-11-03 MX MX2013004923A patent/MX2013004923A/es not_active Application Discontinuation
- 2011-11-03 EP EP11785536.1A patent/EP2635584A1/en not_active Withdrawn
- 2011-11-03 RU RU2013125755/04A patent/RU2013125755A/ru not_active Application Discontinuation
- 2011-11-03 SG SG2013033618A patent/SG190098A1/en unknown
- 2011-11-03 CN CN2011800533551A patent/CN103298815A/zh active Pending
- 2011-11-03 JP JP2013537811A patent/JP2013541588A/ja active Pending
- 2011-11-04 AR ARP110104111A patent/AR083756A1/es unknown
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2013
- 2013-04-22 IL IL225884A patent/IL225884A0/en unknown
- 2013-04-24 ZA ZA2013/02996A patent/ZA201302996B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN103298815A (zh) | 2013-09-11 |
| JP2013541588A (ja) | 2013-11-14 |
| ZA201302996B (en) | 2014-06-25 |
| WO2012061565A1 (en) | 2012-05-10 |
| RU2013125755A (ru) | 2014-12-10 |
| US20120122898A1 (en) | 2012-05-17 |
| US8735408B2 (en) | 2014-05-27 |
| AU2011323371A1 (en) | 2013-05-23 |
| TW201302754A (zh) | 2013-01-16 |
| EP2635584A1 (en) | 2013-09-11 |
| IL225884A0 (en) | 2013-07-31 |
| AR083756A1 (es) | 2013-03-20 |
| MX2013004923A (es) | 2013-06-28 |
| BR112013011094A2 (pt) | 2016-08-23 |
| CA2817112A1 (en) | 2011-11-05 |
| SG190098A1 (en) | 2013-06-28 |
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