CA2629132C - Pyrimidylaminobenzamide derivatives for the treatment of neurofibromatosis - Google Patents
Pyrimidylaminobenzamide derivatives for the treatment of neurofibromatosis Download PDFInfo
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- CA2629132C CA2629132C CA2629132A CA2629132A CA2629132C CA 2629132 C CA2629132 C CA 2629132C CA 2629132 A CA2629132 A CA 2629132A CA 2629132 A CA2629132 A CA 2629132A CA 2629132 C CA2629132 C CA 2629132C
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- lower alkyl
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- 238000011282 treatment Methods 0.000 title claims abstract description 32
- 208000009905 Neurofibromatoses Diseases 0.000 title description 17
- 201000004931 neurofibromatosis Diseases 0.000 title description 17
- 208000013355 benign neoplasm of brain Diseases 0.000 claims abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 23
- 208000003019 Neurofibromatosis 1 Diseases 0.000 claims description 15
- 208000024834 Neurofibromatosis type 1 Diseases 0.000 claims description 14
- 239000005517 L01XE01 - Imatinib Substances 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 claims description 8
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- 230000002265 prevention Effects 0.000 claims description 6
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- 239000003937 drug carrier Substances 0.000 claims description 2
- HHZIURLSWUIHRB-UHFFFAOYSA-N nilotinib Chemical compound C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HHZIURLSWUIHRB-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
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- HLIBNTOXKQCYMV-UHFFFAOYSA-N propylsulfamic acid Chemical compound CCCNS(O)(=O)=O HLIBNTOXKQCYMV-UHFFFAOYSA-N 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000011519 second-line treatment Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 230000037370 skin discoloration Effects 0.000 description 1
- 210000001154 skull base Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 231100000886 tinnitus Toxicity 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- A61K31/495—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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74278105P | 2005-12-06 | 2005-12-06 | |
| US60/742,781 | 2005-12-06 | ||
| PCT/EP2006/069335 WO2007065898A1 (en) | 2005-12-06 | 2006-12-05 | Pyrimidylaminobenzamide derivatives for the treatment of neurofibromatosis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2629132A1 CA2629132A1 (en) | 2007-06-14 |
| CA2629132C true CA2629132C (en) | 2014-05-27 |
Family
ID=37831665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2629132A Expired - Fee Related CA2629132C (en) | 2005-12-06 | 2006-12-05 | Pyrimidylaminobenzamide derivatives for the treatment of neurofibromatosis |
Country Status (13)
| Country | Link |
|---|---|
| US (4) | US20080318988A1 (enExample) |
| EP (2) | EP1959957B1 (enExample) |
| JP (4) | JP2009518358A (enExample) |
| KR (2) | KR101498848B1 (enExample) |
| CN (1) | CN101321532B (enExample) |
| AU (1) | AU2006323992B2 (enExample) |
| BR (1) | BRPI0619416A2 (enExample) |
| CA (1) | CA2629132C (enExample) |
| ES (2) | ES2549327T3 (enExample) |
| PL (1) | PL1959957T3 (enExample) |
| PT (1) | PT1959957E (enExample) |
| RU (1) | RU2450814C2 (enExample) |
| WO (1) | WO2007065898A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2450814C2 (ru) * | 2005-12-06 | 2012-05-20 | Новартис Аг | Производные пиримидиламинобензамида, предназначенные для лечения нейрофиброматоза |
| US8242271B2 (en) | 2007-06-04 | 2012-08-14 | Avila Therapeutics, Inc. | Heterocyclic compounds and uses thereof |
| WO2009158447A2 (en) * | 2008-06-27 | 2009-12-30 | Indiana University Research And Technology Corporation | Materials and methods for suppressing and/or treating neurofibroma and related tumors |
| KR20110053354A (ko) * | 2008-08-13 | 2011-05-20 | 노파르티스 아게 | 폐동맥 고혈압의 치료 |
| EP2186514B1 (en) | 2008-11-14 | 2016-06-29 | Kinki University | Treatment of Malignant Peripheral Nerve Sheath Tumors |
| BR112012009094A8 (pt) * | 2009-10-23 | 2017-10-10 | Novartis Ag | método de tratamento de transtornos proliferativos e outras condições patológicas mediadas por bcr-abl, c-kit, ddr1,ddr2 ou atividade pdgf-r quinase |
| JP7230817B2 (ja) | 2017-10-03 | 2023-03-01 | 凸版印刷株式会社 | 超音波シール用アンビル及び超音波シール装置 |
| TWI787523B (zh) | 2018-06-15 | 2022-12-21 | 漢達生技醫藥股份有限公司 | 達沙替尼十二烷基硫酸鹽之結晶 |
| WO2026035611A1 (en) * | 2024-08-05 | 2026-02-12 | Amo Pharma Ltd | Methods of treating neurofibromatosis using farnesyl dibenzodiazepinones |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0215676D0 (en) * | 2002-07-05 | 2002-08-14 | Novartis Ag | Organic compounds |
| GB0325031D0 (en) | 2003-10-27 | 2003-12-03 | Novartis Ag | Organic compounds |
| SI1686997T1 (sl) * | 2003-11-18 | 2009-08-31 | Novartis Ag | Inhibitorji mutantne oblike KIT |
| PT1843771E (pt) * | 2005-01-28 | 2011-12-02 | Novartis Ag | Uso de pirimidilaminobenzamidas para o tratamento de doenças que respondem à modulação da atividade da cinase tie-2 |
| RU2450814C2 (ru) * | 2005-12-06 | 2012-05-20 | Новартис Аг | Производные пиримидиламинобензамида, предназначенные для лечения нейрофиброматоза |
-
2006
- 2006-12-05 RU RU2008127264/15A patent/RU2450814C2/ru not_active IP Right Cessation
- 2006-12-05 ES ES10150521.2T patent/ES2549327T3/es active Active
- 2006-12-05 CN CN2006800456624A patent/CN101321532B/zh not_active Expired - Fee Related
- 2006-12-05 PT PT06830381T patent/PT1959957E/pt unknown
- 2006-12-05 AU AU2006323992A patent/AU2006323992B2/en not_active Ceased
- 2006-12-05 BR BRPI0619416-8A patent/BRPI0619416A2/pt active Search and Examination
- 2006-12-05 WO PCT/EP2006/069335 patent/WO2007065898A1/en not_active Ceased
- 2006-12-05 EP EP06830381A patent/EP1959957B1/en not_active Not-in-force
- 2006-12-05 ES ES06830381T patent/ES2391199T3/es active Active
- 2006-12-05 JP JP2008543819A patent/JP2009518358A/ja not_active Withdrawn
- 2006-12-05 KR KR1020137034055A patent/KR101498848B1/ko not_active Expired - Fee Related
- 2006-12-05 PL PL06830381T patent/PL1959957T3/pl unknown
- 2006-12-05 CA CA2629132A patent/CA2629132C/en not_active Expired - Fee Related
- 2006-12-05 KR KR1020087013614A patent/KR101413387B1/ko not_active Expired - Fee Related
- 2006-12-05 EP EP10150521.2A patent/EP2177222B1/en not_active Not-in-force
- 2006-12-06 US US12/095,956 patent/US20080318988A1/en not_active Abandoned
-
2010
- 2010-03-24 US US12/730,590 patent/US20100234408A1/en not_active Abandoned
-
2012
- 2012-12-05 US US13/706,249 patent/US8604045B2/en not_active Expired - Fee Related
-
2013
- 2013-02-04 JP JP2013019700A patent/JP2013107893A/ja not_active Withdrawn
- 2013-11-08 US US14/075,256 patent/US20140073660A1/en not_active Abandoned
-
2014
- 2014-11-28 JP JP2014240970A patent/JP2015091818A/ja not_active Withdrawn
-
2017
- 2017-05-16 JP JP2017097077A patent/JP2017193553A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0619416A2 (pt) | 2011-10-04 |
| CN101321532A (zh) | 2008-12-10 |
| US20140073660A1 (en) | 2014-03-13 |
| JP2017193553A (ja) | 2017-10-26 |
| KR20080077973A (ko) | 2008-08-26 |
| PT1959957E (pt) | 2012-10-29 |
| PL1959957T3 (pl) | 2012-12-31 |
| KR101498848B1 (ko) | 2015-03-05 |
| KR101413387B1 (ko) | 2014-06-27 |
| RU2450814C2 (ru) | 2012-05-20 |
| ES2391199T3 (es) | 2012-11-22 |
| EP2177222B1 (en) | 2015-07-15 |
| EP1959957B1 (en) | 2012-07-18 |
| US20080318988A1 (en) | 2008-12-25 |
| EP1959957A1 (en) | 2008-08-27 |
| AU2006323992A1 (en) | 2007-06-14 |
| KR20140022431A (ko) | 2014-02-24 |
| CA2629132A1 (en) | 2007-06-14 |
| JP2015091818A (ja) | 2015-05-14 |
| EP2177222A1 (en) | 2010-04-21 |
| RU2008127264A (ru) | 2010-01-20 |
| WO2007065898A1 (en) | 2007-06-14 |
| ES2549327T3 (es) | 2015-10-27 |
| US20100234408A1 (en) | 2010-09-16 |
| JP2009518358A (ja) | 2009-05-07 |
| AU2006323992B2 (en) | 2010-07-08 |
| CN101321532B (zh) | 2011-06-29 |
| US8604045B2 (en) | 2013-12-10 |
| US20130123290A1 (en) | 2013-05-16 |
| JP2013107893A (ja) | 2013-06-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20191205 |