RU2489430C2 - Производные 4-аминопиримидина - Google Patents
Производные 4-аминопиримидина Download PDFInfo
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- RU2489430C2 RU2489430C2 RU2010130418/04A RU2010130418A RU2489430C2 RU 2489430 C2 RU2489430 C2 RU 2489430C2 RU 2010130418/04 A RU2010130418/04 A RU 2010130418/04A RU 2010130418 A RU2010130418 A RU 2010130418A RU 2489430 C2 RU2489430 C2 RU 2489430C2
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- 150000005007 4-aminopyrimidines Chemical class 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 473
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 192
- 125000005843 halogen group Chemical group 0.000 claims abstract description 51
- 125000003118 aryl group Chemical group 0.000 claims abstract description 45
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 44
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 43
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- 125000004429 atom Chemical group 0.000 claims abstract description 26
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
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- 201000010099 disease Diseases 0.000 claims abstract description 24
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- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 230000003042 antagnostic effect Effects 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 386
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 169
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 65
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 49
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- 125000002619 bicyclic group Chemical group 0.000 claims description 43
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 42
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- 229960001340 histamine Drugs 0.000 claims description 27
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 17
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- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
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- SXZIXHOMFPUIRK-UHFFFAOYSA-N diphenylmethanimine Chemical compound C=1C=CC=CC=1C(=N)C1=CC=CC=C1 SXZIXHOMFPUIRK-UHFFFAOYSA-N 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
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- 239000007858 starting material Substances 0.000 description 17
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- YBCCTTBBUNOCEH-UHFFFAOYSA-N tert-butyl n-[1-(2-tert-butyl-6-chloropyrimidin-4-yl)azetidin-3-yl]-n-methylcarbamate Chemical compound C1C(N(C)C(=O)OC(C)(C)C)CN1C1=CC(Cl)=NC(C(C)(C)C)=N1 YBCCTTBBUNOCEH-UHFFFAOYSA-N 0.000 description 1
- YNQNJVGMBLPFAU-UHFFFAOYSA-N tert-butyl n-[1-(6-chloro-2-cyclopropylpyrimidin-4-yl)azetidin-3-yl]-n-methylcarbamate Chemical compound C1C(N(C)C(=O)OC(C)(C)C)CN1C1=CC(Cl)=NC(C2CC2)=N1 YNQNJVGMBLPFAU-UHFFFAOYSA-N 0.000 description 1
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- KFTXEUQWZLIYLD-UHFFFAOYSA-N tert-butyl n-[1-[6-chloro-2-(cyclopropylmethyl)pyrimidin-4-yl]azetidin-3-yl]-n-methylcarbamate Chemical compound C1C(N(C)C(=O)OC(C)(C)C)CN1C1=CC(Cl)=NC(CC2CC2)=N1 KFTXEUQWZLIYLD-UHFFFAOYSA-N 0.000 description 1
- KBMXPFDYKDWWAC-UHFFFAOYSA-N tert-butyl n-[1-[6-chloro-2-(phenoxymethyl)pyrimidin-4-yl]azetidin-3-yl]-n-methylcarbamate Chemical compound C1C(N(C)C(=O)OC(C)(C)C)CN1C1=CC(Cl)=NC(COC=2C=CC=CC=2)=N1 KBMXPFDYKDWWAC-UHFFFAOYSA-N 0.000 description 1
- XYKYUXYNQDXZTD-MRVPVSSYSA-N tert-butyl n-methyl-n-[(3r)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)[C@@H]1CCNC1 XYKYUXYNQDXZTD-MRVPVSSYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
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- 238000005550 wet granulation Methods 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Rheumatology (AREA)
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- Transplantation (AREA)
- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07382006 | 2007-12-21 | ||
| EP07382006.0 | 2007-12-21 | ||
| US3153408P | 2008-02-26 | 2008-02-26 | |
| US61/031,534 | 2008-02-26 | ||
| PCT/EP2008/067950 WO2009080721A2 (en) | 2007-12-21 | 2008-12-18 | 4 -aminopyrimidine derivatives as histamine h4 receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2010130418A RU2010130418A (ru) | 2012-01-27 |
| RU2489430C2 true RU2489430C2 (ru) | 2013-08-10 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| RU2010130418/04A RU2489430C2 (ru) | 2007-12-21 | 2008-12-18 | Производные 4-аминопиримидина |
Country Status (24)
| Country | Link |
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| US (1) | US8431580B2 (enExample) |
| EP (1) | EP2235012B1 (enExample) |
| JP (1) | JP5498396B2 (enExample) |
| KR (1) | KR101639819B1 (enExample) |
| CN (1) | CN101903385B (enExample) |
| AR (1) | AR069814A1 (enExample) |
| AU (1) | AU2008341678B2 (enExample) |
| BR (1) | BRPI0820779B8 (enExample) |
| CA (1) | CA2709650C (enExample) |
| CL (1) | CL2008003811A1 (enExample) |
| CY (1) | CY1114427T1 (enExample) |
| DK (1) | DK2235012T3 (enExample) |
| ES (1) | ES2430210T3 (enExample) |
| HR (1) | HRP20130918T1 (enExample) |
| IL (1) | IL206413A (enExample) |
| PE (1) | PE20091330A1 (enExample) |
| PL (1) | PL2235012T3 (enExample) |
| PT (1) | PT2235012E (enExample) |
| RU (1) | RU2489430C2 (enExample) |
| SI (1) | SI2235012T1 (enExample) |
| TW (1) | TWI429440B (enExample) |
| UA (1) | UA101963C2 (enExample) |
| WO (1) | WO2009080721A2 (enExample) |
| ZA (1) | ZA201005179B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12234227B2 (en) | 2018-10-19 | 2025-02-25 | Nxera Pharma Uk Limited | Pyrazole derivatives as H4 antagonist compounds |
| RU2837355C1 (ru) * | 2020-04-22 | 2025-03-31 | НКСЕРА ФАРМА Юкей ЛИМИТЕД | Соединения-антагонисты н4 |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007026341A1 (de) | 2007-06-06 | 2008-12-11 | Merck Patent Gmbh | Benzoxazolonderivate |
| DE102007032507A1 (de) | 2007-07-12 | 2009-04-02 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102007061963A1 (de) | 2007-12-21 | 2009-06-25 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102008019907A1 (de) | 2008-04-21 | 2009-10-22 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102008028905A1 (de) | 2008-06-18 | 2009-12-24 | Merck Patent Gmbh | 3-(3-Pyrimidin-2-yl-benzyl)-[1,2,4]triazolo[4,3-b]pyridazinderivate |
| EA019320B1 (ru) | 2008-12-22 | 2014-02-28 | Мерк Патент Гмбх | Новые полиморфные формы дигидрофосфата 6-(1-метил-1h-пиразол-4-ил)-2-{3-[5-(2-морфолин-4-илэтокси)пиримидин-2-ил]бензил}-2h-пиридазин-3-она и способы их получения |
| EP2201982A1 (en) | 2008-12-24 | 2010-06-30 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Histamine H4 receptor antagonists for the treatment of vestibular disorders |
| JP5759471B2 (ja) | 2009-10-29 | 2015-08-05 | ヴェクチュラ リミテッド | Ｊａｋ３キナーゼ阻害剤としての窒素含有ヘテロアリール誘導体 |
| JP5781537B2 (ja) * | 2009-12-23 | 2015-09-24 | メディシス ファーマシューティカル コーポレイション | ヒスタミンｈ４受容体アンタゴニストとしてのアミノアルキルピリミジン誘導体 |
| HUE039713T2 (hu) | 2012-06-08 | 2019-02-28 | Sensorion | H4 receptor inhibitorok tinnitus kezelésére |
| ES2946551T3 (es) | 2017-10-17 | 2023-07-20 | Palau Pharma S L U | Síntesis de compuestos de 4-aminopirimidina |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1505064A1 (en) * | 2003-08-05 | 2005-02-09 | Bayer HealthCare AG | 2-Aminopyrimidine derivatives |
| RU2004126680A (ru) * | 2002-02-05 | 2005-04-10 | Ново Нордиск А/С (DK) | Новые арил-и гетероарилипиперазины |
| WO2005054239A1 (en) * | 2003-12-05 | 2005-06-16 | Bayer Healthcare Ag | 2-aminopyrimidine derivatives |
| WO2007031529A1 (en) * | 2005-09-13 | 2007-03-22 | Palau Pharma, S.A. | 2-aminopyrimidine derivatives as modulators of the histamine h4 receptor activity |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2551944A1 (en) * | 2003-12-15 | 2005-06-30 | Almirall Prodesfarma Ag | 2, 6 bisheteroaryl-4-aminopyrimidines as adenosine receptor antagonists |
| DE602006020864D1 (de) * | 2005-04-11 | 2011-05-05 | Almirall Sa | 2, 6-di-(hetero-)aryl-4-amido-pyrimidine als adenosin-rezeptor-antagonisten |
| WO2007084914A2 (en) * | 2006-01-17 | 2007-07-26 | Neurocrine Biosciences, Inc. | Phenoxy-substituted pyrimidines as adenosine receptor antagonists |
-
2008
- 2008-12-18 RU RU2010130418/04A patent/RU2489430C2/ru active
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- 2008-12-18 DK DK08865603.8T patent/DK2235012T3/da active
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- 2008-12-18 SI SI200831056T patent/SI2235012T1/sl unknown
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- 2008-12-18 CL CL2008003811A patent/CL2008003811A1/es unknown
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2010
- 2010-06-16 IL IL206413A patent/IL206413A/en active IP Right Grant
- 2010-07-20 ZA ZA2010/05179A patent/ZA201005179B/en unknown
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2013
- 2013-09-10 CY CY20131100781T patent/CY1114427T1/el unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2004126680A (ru) * | 2002-02-05 | 2005-04-10 | Ново Нордиск А/С (DK) | Новые арил-и гетероарилипиперазины |
| EP1505064A1 (en) * | 2003-08-05 | 2005-02-09 | Bayer HealthCare AG | 2-Aminopyrimidine derivatives |
| WO2005054239A1 (en) * | 2003-12-05 | 2005-06-16 | Bayer Healthcare Ag | 2-aminopyrimidine derivatives |
| WO2007031529A1 (en) * | 2005-09-13 | 2007-03-22 | Palau Pharma, S.A. | 2-aminopyrimidine derivatives as modulators of the histamine h4 receptor activity |
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| ZHANG M. et al. The histamine H4 receptor in autoimmune disease. Expert Opinion on Investigational Drugs. 15(11), 2006, p.1443-1452. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12234227B2 (en) | 2018-10-19 | 2025-02-25 | Nxera Pharma Uk Limited | Pyrazole derivatives as H4 antagonist compounds |
| RU2837355C1 (ru) * | 2020-04-22 | 2025-03-31 | НКСЕРА ФАРМА Юкей ЛИМИТЕД | Соединения-антагонисты н4 |
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