CA2712612A1 - 4-(pyrrolo[2,3-c]pyridine-3-yl)pyrimidin-2-ylamine derivatives - Google Patents
4-(pyrrolo[2,3-c]pyridine-3-yl)pyrimidin-2-ylamine derivatives Download PDFInfo
- Publication number
- CA2712612A1 CA2712612A1 CA2712612A CA2712612A CA2712612A1 CA 2712612 A1 CA2712612 A1 CA 2712612A1 CA 2712612 A CA2712612 A CA 2712612A CA 2712612 A CA2712612 A CA 2712612A CA 2712612 A1 CA2712612 A1 CA 2712612A1
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- ULPADEPZZAIIOV-UHFFFAOYSA-N 4-(1h-pyrrolo[2,3-c]pyridin-3-yl)pyrimidin-2-amine Chemical class NC1=NC=CC(C=2C3=CC=NC=C3NC=2)=N1 ULPADEPZZAIIOV-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 143
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 36
- 238000011282 treatment Methods 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 7
- 208000026310 Breast neoplasm Diseases 0.000 claims description 7
- 230000001028 anti-proliverative effect Effects 0.000 claims description 7
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- 206010009944 Colon cancer Diseases 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000262 estrogen Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 5
- 229910052786 argon Inorganic materials 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
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- 231100000599 cytotoxic agent Toxicity 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
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- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
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- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 3
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- -1 aminopyrimidinyl Chemical class 0.000 description 108
- 235000013350 formula milk Nutrition 0.000 description 61
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- 239000004480 active ingredient Substances 0.000 description 37
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 24
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
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- 238000006243 chemical reaction Methods 0.000 description 15
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- 210000003932 urinary bladder Anatomy 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 229960000653 valrubicin Drugs 0.000 description 1
- ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 229960005212 vindesine sulfate Drugs 0.000 description 1
- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 description 1
- 229960000922 vinflunine Drugs 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- FBTUMDXHSRTGRV-ALTNURHMSA-N zorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(\C)=N\NC(=O)C=1C=CC=CC=1)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 FBTUMDXHSRTGRV-ALTNURHMSA-N 0.000 description 1
- 229960000641 zorubicin Drugs 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Hematology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008005493.3 | 2008-01-22 | ||
| DE102008005493A DE102008005493A1 (de) | 2008-01-22 | 2008-01-22 | 4-(Pyrrolo[2,3-c] pyridine-3-yl)-pyrimidin-2-yl-amin-derivate |
| PCT/EP2008/011098 WO2009092431A1 (de) | 2008-01-22 | 2008-12-23 | 4-(pyrrolo[2,3-c]pyridine-3-yl)-pyrimidin-2-amin-derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2712612A1 true CA2712612A1 (en) | 2009-07-30 |
Family
ID=40386204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2712612A Abandoned CA2712612A1 (en) | 2008-01-22 | 2008-12-23 | 4-(pyrrolo[2,3-c]pyridine-3-yl)pyrimidin-2-ylamine derivatives |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20100292262A1 (OSRAM) |
| EP (1) | EP2231664A1 (OSRAM) |
| JP (1) | JP5524864B2 (OSRAM) |
| KR (1) | KR20100112626A (OSRAM) |
| CN (1) | CN101918404A (OSRAM) |
| AR (1) | AR070212A1 (OSRAM) |
| AU (1) | AU2008348816B2 (OSRAM) |
| BR (1) | BRPI0821936A2 (OSRAM) |
| CA (1) | CA2712612A1 (OSRAM) |
| DE (1) | DE102008005493A1 (OSRAM) |
| IL (1) | IL206905A0 (OSRAM) |
| MX (1) | MX2010007927A (OSRAM) |
| WO (1) | WO2009092431A1 (OSRAM) |
| ZA (1) | ZA201005959B (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101723936B (zh) * | 2008-10-27 | 2014-01-15 | 上海睿星基因技术有限公司 | 激酶抑制剂及其在药学中的用途 |
| JP2014515368A (ja) | 2011-05-26 | 2014-06-30 | 第一三共株式会社 | プロテインキナーゼ阻害剤としての複素環化合物 |
| DK2922828T3 (da) | 2012-11-21 | 2020-08-31 | Ptc Therapeutics Inc | 4,6-diamino-pyrimidin-derivater som bmi-1-inhibitorer til at behandle cancer |
| TWI663166B (zh) | 2013-04-24 | 2019-06-21 | 健生藥品公司 | 新化合物 |
| CA2922657C (en) * | 2013-08-30 | 2022-04-12 | Ptc Therapeutics, Inc. | Substituted pyrimidine bmi-1 inhibitors |
| TWI704146B (zh) | 2013-09-26 | 2020-09-11 | 比利時商健生藥品公司 | 用作ＮＩＫ抑制劑之新的1-(４-嘧啶基)-１Ｈ-吡唑並[３,２-ｃ]吡啶衍生物 |
| TWI627173B (zh) | 2013-09-26 | 2018-06-21 | 比利時商健生藥品公司 | 作為ＮＩＫ抑制劑的新穎３－（１Ｈ－吡唑－４－基）－１Ｈ－吡咯并［２，３－ｃ］吡啶衍生物 |
| US10584115B2 (en) | 2013-11-21 | 2020-03-10 | Ptc Therapeutics, Inc. | Substituted pyridine and pyrazine BMI-1 inhibitors |
| CN107074882B (zh) | 2014-10-23 | 2019-07-30 | 詹森药业有限公司 | 作为nik抑制剂的新的吡唑并嘧啶衍生物 |
| KR102500071B1 (ko) | 2014-10-23 | 2023-02-14 | 얀센 파마슈티카 엔.브이. | Ｎｉｋ 억제제로서의 신규 화합물 |
| ES2704749T3 (es) | 2014-10-23 | 2019-03-19 | Janssen Pharmaceutica Nv | Nuevos derivados de pirazol en calidad de inhibidores de nik |
| EA033238B1 (ru) | 2014-10-23 | 2019-09-30 | Янссен Фармацевтика Нв | Новые производные тиенопиримидина в качестве ингибиторов nik |
| BR112021002630A2 (pt) | 2018-08-17 | 2021-05-11 | Ptc Therapeutics, Inc. | método para tratar câncer pancreático |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5747469A (en) | 1991-03-06 | 1998-05-05 | Board Of Regents, The University Of Texas System | Methods and compositions comprising DNA damaging agents and p53 |
| GB9904387D0 (en) | 1999-02-25 | 1999-04-21 | Pharmacia & Upjohn Spa | Antitumour synergistic composition |
| GB0308466D0 (en) | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| WO2005123672A2 (en) * | 2004-06-14 | 2005-12-29 | Takeda San Diego, Inc. | Kinase inhibitors |
| WO2006050076A1 (en) | 2004-10-29 | 2006-05-11 | Janssen Pharmaceutica, N.V. | Pyrimidinyl substituted fused-pyrrolyl compounds useful in treating kinase disorders |
| KR20080063809A (ko) * | 2005-09-30 | 2008-07-07 | 버텍스 파마슈티칼스 인코포레이티드 | 야누스 키나아제의 억제제로서 유용한 데아자퓨린 |
| DE102006012617A1 (de) * | 2006-03-20 | 2007-09-27 | Merck Patent Gmbh | 4-(Pyrrolopyridinyl)-pyrimidinyl-2-amin-derivate |
-
2008
- 2008-01-22 DE DE102008005493A patent/DE102008005493A1/de not_active Withdrawn
- 2008-12-23 AU AU2008348816A patent/AU2008348816B2/en not_active Ceased
- 2008-12-23 JP JP2010543386A patent/JP5524864B2/ja not_active Expired - Fee Related
- 2008-12-23 KR KR1020107018575A patent/KR20100112626A/ko not_active Withdrawn
- 2008-12-23 WO PCT/EP2008/011098 patent/WO2009092431A1/de not_active Ceased
- 2008-12-23 US US12/863,817 patent/US20100292262A1/en not_active Abandoned
- 2008-12-23 CA CA2712612A patent/CA2712612A1/en not_active Abandoned
- 2008-12-23 CN CN200880125171XA patent/CN101918404A/zh active Pending
- 2008-12-23 MX MX2010007927A patent/MX2010007927A/es not_active Application Discontinuation
- 2008-12-23 BR BRPI0821936-2A patent/BRPI0821936A2/pt not_active IP Right Cessation
- 2008-12-23 EP EP08871371A patent/EP2231664A1/de not_active Withdrawn
-
2009
- 2009-01-21 AR ARP090100174A patent/AR070212A1/es unknown
-
2010
- 2010-07-08 IL IL206905A patent/IL206905A0/en unknown
- 2010-08-20 ZA ZA2010/05959A patent/ZA201005959B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP5524864B2 (ja) | 2014-06-18 |
| AR070212A1 (es) | 2010-03-25 |
| IL206905A0 (en) | 2010-12-30 |
| JP2011510028A (ja) | 2011-03-31 |
| ZA201005959B (en) | 2011-04-28 |
| WO2009092431A1 (de) | 2009-07-30 |
| EP2231664A1 (de) | 2010-09-29 |
| KR20100112626A (ko) | 2010-10-19 |
| DE102008005493A8 (de) | 2010-03-25 |
| AU2008348816A1 (en) | 2009-07-30 |
| AU2008348816B2 (en) | 2011-10-20 |
| BRPI0821936A2 (pt) | 2015-06-16 |
| DE102008005493A1 (de) | 2009-07-23 |
| CN101918404A (zh) | 2010-12-15 |
| MX2010007927A (es) | 2010-08-09 |
| US20100292262A1 (en) | 2010-11-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20131220 |
|
| FZDE | Discontinued |
Effective date: 20151223 |