UA79460C2 - Benzoxazinone derived compounds, method for their preparation, intermediate, medicaments containing these compounds - Google Patents
Benzoxazinone derived compounds, method for their preparation, intermediate, medicaments containing these compounds Download PDFInfo
- Publication number
- UA79460C2 UA79460C2 UA20041109155A UA20041109155A UA79460C2 UA 79460 C2 UA79460 C2 UA 79460C2 UA 20041109155 A UA20041109155 A UA 20041109155A UA 20041109155 A UA20041109155 A UA 20041109155A UA 79460 C2 UA79460 C2 UA 79460C2
- Authority
- UA
- Ukraine
- Prior art keywords
- oxo
- piperidin
- monosubstituted
- optionally
- oxazin
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 74
- 238000000034 method Methods 0.000 title claims abstract description 34
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 239000003814 drug Substances 0.000 title abstract description 7
- -1 monosubstituted aliphatic radical Chemical class 0.000 claims description 257
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 141
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 116
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 113
- 229920006395 saturated elastomer Polymers 0.000 claims description 109
- 150000003254 radicals Chemical class 0.000 claims description 86
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 70
- 125000005842 heteroatom Chemical group 0.000 claims description 69
- 125000002950 monocyclic group Chemical group 0.000 claims description 67
- 125000001424 substituent group Chemical group 0.000 claims description 59
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 39
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
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- 125000005418 aryl aryl group Chemical group 0.000 claims description 27
- 239000012453 solvate Substances 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
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- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- NOUWNNABOUGTDQ-UHFFFAOYSA-N octane Chemical compound CCCCCCC[CH2+] NOUWNNABOUGTDQ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008014 pharmaceutical binder Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 235000013550 pizza Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical class C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- PIDHNVVHJDBAAL-UHFFFAOYSA-N tert-butyl 4-(6-chloro-2-oxo-4h-3,1-benzoxazin-1-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1C2=CC=C(Cl)C=C2COC1=O PIDHNVVHJDBAAL-UHFFFAOYSA-N 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
- A61K31/536—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 ortho- or peri-condensed with carbocyclic ring systems
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Obesity (AREA)
- Immunology (AREA)
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- Rheumatology (AREA)
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- Hospice & Palliative Care (AREA)
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- Nutrition Science (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200200813A ES2193875B2 (es) | 2002-04-09 | 2002-04-09 | Derivados de benzoxazinona, su preparacion y su aplicacion como medicamentos. |
| PCT/EP2003/003629 WO2003084952A1 (en) | 2002-04-09 | 2003-04-08 | Benzoxazinone-derived compounds, their preparation und use as medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA79460C2 true UA79460C2 (en) | 2007-06-25 |
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| UA20041109155A UA79460C2 (en) | 2002-04-09 | 2003-08-04 | Benzoxazinone derived compounds, method for their preparation, intermediate, medicaments containing these compounds |
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| EP (2) | EP1497285B1 (es) |
| JP (1) | JP2005529866A (es) |
| KR (1) | KR20050008679A (es) |
| CN (1) | CN1659164A (es) |
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| AT (2) | ATE489382T1 (es) |
| AU (2) | AU2003222804A1 (es) |
| BR (1) | BR0309083A (es) |
| CA (1) | CA2481701A1 (es) |
| DE (2) | DE60335094D1 (es) |
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| EC (1) | ECSP045353A (es) |
| ES (3) | ES2193875B2 (es) |
| HK (1) | HK1069820A1 (es) |
| HR (1) | HRP20040919A2 (es) |
| IL (1) | IL164442A0 (es) |
| IS (1) | IS7491A (es) |
| MA (1) | MA27692A1 (es) |
| MX (1) | MXPA04009889A (es) |
| NO (1) | NO20044322L (es) |
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| PL (1) | PL372537A1 (es) |
| PT (1) | PT1500654E (es) |
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| UA (1) | UA79460C2 (es) |
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| ES2193875B2 (es) * | 2002-04-09 | 2005-03-01 | Laboratorios Del Dr. Esteve, S.A. | Derivados de benzoxazinona, su preparacion y su aplicacion como medicamentos. |
| ES2228267B1 (es) * | 2003-07-30 | 2006-07-01 | Laboratorios Del Dr. Esteve, S.A. | Combinacion de sustancias activas conteniendo al menos un compuesto con afinidad por el receptor del neuropeptido y (npy) y al menos un compuesto con afinidad por el receptor 5-ht6. |
| ES2222833B1 (es) * | 2003-07-30 | 2006-03-01 | Laboratorios Del Dr. Esteve, S.A. | Compuestos piperidinicos 1,4-disustituidos, su preparacion y su uso como medicamentos. |
| ES2228268B1 (es) * | 2003-07-30 | 2006-07-01 | Laboratorios Del Dr. Esteve, S.A. | Combinacion de sustancias activas conteniendo al menos un compuesto con afinidad por el receptor del neuropeptido y (npy) y al menos un compuesto con afinidad por el receptor 5-ht6. |
| WO2005090340A1 (ja) * | 2004-03-22 | 2005-09-29 | Banyu Pharmaceutical Co., Ltd. | ピペリジン－１－カルボキサミド誘導体 |
| US8147853B2 (en) | 2005-02-15 | 2012-04-03 | The Procter & Gamble Company | Personal care compositions containing hydrophobically modified non-platelet particles |
| EP1861066A2 (en) * | 2005-03-21 | 2007-12-05 | The Procter and Gamble Company | Multi-phase personal care composition comprising visually distinct phases |
| CA2603299A1 (en) * | 2005-04-13 | 2006-10-26 | The Procter & Gamble Company | Structured multi-phased personal care composition comprising branched anionic surfactants |
| US7820609B2 (en) | 2005-04-13 | 2010-10-26 | The Procter & Gamble Company | Mild, structured, multi-phase personal cleansing compositions comprising density modifiers |
| ITMI20050909A1 (it) * | 2005-05-19 | 2006-11-20 | Acraf | Uso di un benzoil derivato dal 3-ammino-carbazolo per la produzione di un farmaco per il trattamento di un disturbo associato alla produzione di prostaglandina e2-pge2- |
| US20120015009A9 (en) * | 2005-06-07 | 2012-01-19 | The Procter & Gamble Company | Multi-phased personal care composition comprising a blooming perfume composition |
| ITMI20051523A1 (it) * | 2005-08-03 | 2007-02-04 | Acraf | Composto del 3-ammino-carbazolo composizione farmaceutica che lo contiene e metodo per prepararlo |
| WO2007066310A2 (en) * | 2005-12-08 | 2007-06-14 | The Procter & Gamble Company | A container comprising an in-mold label positioned proximate to a surface topography |
| US20070167338A1 (en) * | 2006-01-09 | 2007-07-19 | Mchugh Colin M | Multiphase personal care compositions comprising beads |
| US8104616B2 (en) | 2006-02-11 | 2012-01-31 | The Procter & Gamble Company | Clamshell package for holding and displaying consumer products |
| US8153144B2 (en) * | 2006-02-28 | 2012-04-10 | The Proctor & Gamble Company | Stable multiphase composition comprising alkylamphoacetate |
| WO2008020455A2 (en) * | 2006-08-14 | 2008-02-21 | Council Of Scientific & Industrial Research | Pyrrolo[2,1-c][1,4]benzodiazepine hybrids and a process for the preparation thereof |
| EP1902733A1 (en) * | 2006-09-19 | 2008-03-26 | Laboratorios Del Dr. Esteve, S.A. | Combination of a NMDA-receptor ligand and a compound with 5-HT6 receptor affinity |
| CL2007003044A1 (es) * | 2006-10-24 | 2008-07-04 | Wyeth Corp | Compuestos derivados de benzoxazina; composicion farmaceutica que los comprende; y uso para el tratamiento de un trastorno psicotico, bipolar, depresivo y abuso o dependencia de sustancias entre otros. |
| US20090028808A1 (en) * | 2007-07-27 | 2009-01-29 | The Procter & Gamble Company | Personal care article for sequentially dispensing compositions with variable concentrations of partitioned benefit or suspended benefit agents |
| US20090028809A1 (en) * | 2007-07-27 | 2009-01-29 | Jonathan Robert Cetti | Personal care article for sequentially dispensing compositions with variable concentrations of hydrophobic benefit materials |
| US20090029900A1 (en) * | 2007-07-27 | 2009-01-29 | The Procter & Gamble Company | Personal care article for sequentially dispensing compositions with distinct fragrance characters |
| US7733945B2 (en) * | 2008-03-18 | 2010-06-08 | On-Ramp Wireless, Inc. | Spread spectrum with doppler optimization |
| US20090275574A1 (en) * | 2008-05-05 | 2009-11-05 | Astrazeneca Ab | Novel compounds-300 |
| WO2010101246A1 (ja) * | 2009-03-05 | 2010-09-10 | 塩野義製薬株式会社 | Ｎｐｙ ｙ５受容体拮抗作用を有するピペリジンおよびピロリジン誘導体 |
| CN110684043B (zh) * | 2019-08-13 | 2022-09-06 | 温州大学 | 一种c-n轴手性芳胺化合物及其制备方法 |
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| WO1995002405A1 (en) * | 1993-07-16 | 1995-01-26 | Merck & Co., Inc. | Benzoxazinone and benzopyrimidinone piperidinyl tocolytic oxytocin receptor antagonists |
| EP0755392A4 (en) | 1994-04-14 | 1997-05-02 | Merck & Co Inc | ALPHA1C ADRENERGIC RECEPTOR ANTAGONISTS |
| WO1997019682A1 (en) | 1995-12-01 | 1997-06-05 | Synaptic Pharmaceutical Corporation | Aryl sulfonamide and sulfamide derivatives and uses thereof |
| WO1997020823A2 (en) | 1995-12-01 | 1997-06-12 | Novartis Ag | 2-amino quinazoline derivatives as npy receptor antagonists |
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2002
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2003
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- 2003-04-08 AU AU2003222804A patent/AU2003222804A1/en not_active Abandoned
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- 2003-04-08 PL PL03372537A patent/PL372537A1/xx not_active Application Discontinuation
- 2003-04-08 ES ES03718741T patent/ES2356815T3/es not_active Expired - Lifetime
- 2003-04-08 IL IL16444203A patent/IL164442A0/xx unknown
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- 2003-04-08 BR BR0309083-3A patent/BR0309083A/pt not_active IP Right Cessation
- 2003-04-08 CN CN038128853A patent/CN1659164A/zh active Pending
- 2003-04-08 CA CA002481701A patent/CA2481701A1/en not_active Abandoned
- 2003-04-08 WO PCT/EP2003/003629 patent/WO2003084952A1/en active Application Filing
- 2003-04-08 JP JP2003582149A patent/JP2005529866A/ja active Pending
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- 2003-04-08 DE DE60335094T patent/DE60335094D1/de not_active Expired - Lifetime
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- 2003-04-09 EP EP03712152A patent/EP1500654B1/en not_active Expired - Lifetime
- 2003-04-09 DK DK03712152T patent/DK1500654T3/da active
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