RU2015151359A - Синтез 3-(5-амино-2-метил-4-оксохиназолин-3(4н)-ил)пиперидин-2, 6-диона - Google Patents
Синтез 3-(5-амино-2-метил-4-оксохиназолин-3(4н)-ил)пиперидин-2, 6-диона Download PDFInfo
- Publication number
- RU2015151359A RU2015151359A RU2015151359A RU2015151359A RU2015151359A RU 2015151359 A RU2015151359 A RU 2015151359A RU 2015151359 A RU2015151359 A RU 2015151359A RU 2015151359 A RU2015151359 A RU 2015151359A RU 2015151359 A RU2015151359 A RU 2015151359A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- dione
- nitro
- oxazin
- benzo
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title claims 3
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 64
- MMJSZIMFGHOSBC-UHFFFAOYSA-N 2-methyl-5-nitro-3,1-benzoxazin-4-one Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)OC(C)=NC2=C1 MMJSZIMFGHOSBC-UHFFFAOYSA-N 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 22
- NPWMTBZSRRLQNJ-UHFFFAOYSA-N pyroglutamine Chemical compound NC1CCC(=O)NC1=O NPWMTBZSRRLQNJ-UHFFFAOYSA-N 0.000 claims 21
- 239000002904 solvent Substances 0.000 claims 13
- 230000003993 interaction Effects 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 9
- KHEXQYOPAOPUQQ-UHFFFAOYSA-N 3-(2-methyl-5-nitro-4-oxoquinazolin-3-yl)piperidine-2,6-dione Chemical compound CC1=NC2=CC=CC([N+]([O-])=O)=C2C(=O)N1C1CCC(=O)NC1=O KHEXQYOPAOPUQQ-UHFFFAOYSA-N 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 8
- 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 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 claims 7
- -1 cyclic anhydride Chemical class 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- ISSLESFGPVAXKC-UHFFFAOYSA-N n-[3-(2,6-dioxopiperidin-3-yl)-2-methyl-4-oxoquinazolin-5-yl]formamide Chemical compound CC1=NC2=CC=CC(NC=O)=C2C(=O)N1C1CCC(=O)NC1=O ISSLESFGPVAXKC-UHFFFAOYSA-N 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- GGKYLHNARFFORH-UHFFFAOYSA-N 2-amino-6-nitrobenzoic acid Chemical compound NC1=CC=CC([N+]([O-])=O)=C1C(O)=O GGKYLHNARFFORH-UHFFFAOYSA-N 0.000 claims 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 5
- 239000003054 catalyst Substances 0.000 claims 5
- 239000000852 hydrogen donor Substances 0.000 claims 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 4
- RSNPAKAFCAAMBH-UHFFFAOYSA-N 3-(5-amino-2-methyl-4-oxoquinazolin-3-yl)piperidine-2,6-dione Chemical compound CC1=NC2=CC=CC(N)=C2C(=O)N1C1CCC(=O)NC1=O RSNPAKAFCAAMBH-UHFFFAOYSA-N 0.000 claims 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 239000003153 chemical reaction reagent Substances 0.000 claims 4
- 235000019253 formic acid Nutrition 0.000 claims 4
- 238000005984 hydrogenation reaction Methods 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 150000003950 cyclic amides Chemical class 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 claims 2
- BVJRNKXVSYLNFD-UHFFFAOYSA-N 3-(5-amino-2-methyl-4-oxoquinazolin-3-yl)piperidine-2,6-dione;hydrochloride Chemical compound Cl.CC1=NC2=CC=CC(N)=C2C(=O)N1C1CCC(=O)NC1=O BVJRNKXVSYLNFD-UHFFFAOYSA-N 0.000 claims 2
- YCPULGHBTPQLRH-UHFFFAOYSA-N 3-aminopiperidine-2,6-dione;hydron;chloride Chemical group Cl.NC1CCC(=O)NC1=O YCPULGHBTPQLRH-UHFFFAOYSA-N 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical group NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims 2
- 239000012346 acetyl chloride Substances 0.000 claims 2
- 239000003377 acid catalyst Substances 0.000 claims 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 1
- 241001120493 Arene Species 0.000 claims 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical group [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- 239000004280 Sodium formate Substances 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 150000001733 carboxylic acid esters Chemical class 0.000 claims 1
- 150000001925 cycloalkenes Chemical class 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims 1
- 229940013688 formic acid Drugs 0.000 claims 1
- 150000002390 heteroarenes Chemical class 0.000 claims 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 229960000448 lactic acid Drugs 0.000 claims 1
- 239000011981 lindlar catalyst Substances 0.000 claims 1
- 229960002510 mandelic acid Drugs 0.000 claims 1
- 229940041616 menthol Drugs 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910003445 palladium oxide Inorganic materials 0.000 claims 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- 239000010970 precious metal Substances 0.000 claims 1
- PAQZWJGSJMLPMG-UHFFFAOYSA-N propylphosphonic anhydride Substances CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims 1
- 229960000999 sodium citrate dihydrate Drugs 0.000 claims 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims 1
- 235000019254 sodium formate Nutrition 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- 150000003505 terpenes Chemical class 0.000 claims 1
- 235000007586 terpenes Nutrition 0.000 claims 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361818254P | 2013-05-01 | 2013-05-01 | |
| US61/818,254 | 2013-05-01 | ||
| PCT/US2014/036083 WO2014179416A1 (en) | 2013-05-01 | 2014-04-30 | Synthesis of 3-(5-amino-2-methyl-4-oxoquinazolin-3(4h)-yl) piperidine-2,6-dione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2015151359A true RU2015151359A (ru) | 2017-06-06 |
Family
ID=50885008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015151359A RU2015151359A (ru) | 2013-05-01 | 2014-04-30 | Синтез 3-(5-амино-2-метил-4-оксохиназолин-3(4н)-ил)пиперидин-2, 6-диона |
Country Status (26)
| Country | Link |
|---|---|
| US (3) | US9067912B2 (https=) |
| EP (2) | EP3199532A1 (https=) |
| JP (2) | JP6490055B2 (https=) |
| KR (1) | KR20160003228A (https=) |
| CN (2) | CN107935994A (https=) |
| AR (1) | AR096165A1 (https=) |
| AU (2) | AU2014260011A1 (https=) |
| CA (1) | CA2910971A1 (https=) |
| CY (1) | CY1119525T1 (https=) |
| DK (1) | DK2991976T3 (https=) |
| ES (1) | ES2645944T3 (https=) |
| HR (1) | HRP20171535T1 (https=) |
| HU (1) | HUE034770T2 (https=) |
| LT (1) | LT2991976T (https=) |
| MX (1) | MX363652B (https=) |
| NZ (1) | NZ628322A (https=) |
| PH (1) | PH12015502477A1 (https=) |
| PL (1) | PL2991976T3 (https=) |
| PT (1) | PT2991976T (https=) |
| RS (1) | RS56565B1 (https=) |
| RU (1) | RU2015151359A (https=) |
| SG (1) | SG11201508836XA (https=) |
| SI (1) | SI2991976T1 (https=) |
| SM (1) | SMT201700513T1 (https=) |
| TW (1) | TW201536766A (https=) |
| WO (1) | WO2014179416A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2428513T3 (en) | 2006-09-26 | 2017-08-21 | Celgene Corp | 5-substituted quinazolinone derivatives as anti-cancer agents |
| JP5959543B2 (ja) | 2011-03-11 | 2016-08-02 | セルジーン コーポレイション | ３−（５−アミノ−２−メチル−４−オキソ−４ｈ−キナゾリン−３−イル）−ピペリジン−２，６−ジオンの固体形態、並びにそれらの医薬組成物及び使用 |
| ES2814952T3 (es) | 2012-09-04 | 2021-03-29 | Celgene Corp | Isotopólogos de 3-(5-amino-2-metil-4-oxoquinazolin-3(4H)-il) piperidina-2-6-diona y métodos de preparación de los mismos |
| EP3316888A1 (en) | 2015-07-02 | 2018-05-09 | Celgene Corporation | Combination therapy for treatment of hematological cancers and solid tumors |
| CN106083622B (zh) * | 2016-06-16 | 2018-06-19 | 常州齐晖药业有限公司 | 一种甲苯咪唑中间体3,4-二氨基二苯甲酮的制备方法 |
| WO2018165142A1 (en) * | 2017-03-07 | 2018-09-13 | Celgene Corporation | Solid forms of 3-(5-amino-2-methyl-4-oxo-4h-quinazolin-3-yl)-piperidine-2,6-dione, and their pharmaceutical compositions and uses |
| CN113101295A (zh) * | 2020-03-20 | 2021-07-13 | 上海疆云医疗健康科技有限公司 | 二苯乙烯类似物在治疗糖尿病肾脏疾病中的用途 |
| KR20240055046A (ko) * | 2021-09-02 | 2024-04-26 | 신톤 비.브이. | 오시머티닙을 제조하는 방법 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009539878A (ja) * | 2006-06-08 | 2009-11-19 | アレイ バイオファーマ、インコーポレイテッド | キノリン化合物および使用方法 |
| DK2428513T3 (en) * | 2006-09-26 | 2017-08-21 | Celgene Corp | 5-substituted quinazolinone derivatives as anti-cancer agents |
| JP5959543B2 (ja) * | 2011-03-11 | 2016-08-02 | セルジーン コーポレイション | ３−（５−アミノ−２−メチル−４−オキソ−４ｈ−キナゾリン−３−イル）−ピペリジン−２，６−ジオンの固体形態、並びにそれらの医薬組成物及び使用 |
| AU2012229300B2 (en) * | 2011-03-11 | 2017-04-20 | Celgene Corporation | Methods of treating cancer using 3-(5-amino-2-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione |
| ES2814952T3 (es) * | 2012-09-04 | 2021-03-29 | Celgene Corp | Isotopólogos de 3-(5-amino-2-metil-4-oxoquinazolin-3(4H)-il) piperidina-2-6-diona y métodos de preparación de los mismos |
| CA2935495C (en) * | 2013-01-14 | 2021-04-20 | Deuterx, Llc | 3-(5-substituted-4-oxoquinazolin-3(4h)-yl)-3-deutero-piperidine-2,6-dione derivatives |
-
2014
- 2014-04-30 SM SM20170513T patent/SMT201700513T1/it unknown
- 2014-04-30 HR HRP20171535TT patent/HRP20171535T1/hr unknown
- 2014-04-30 AR ARP140101806A patent/AR096165A1/es unknown
- 2014-04-30 LT LTEP14728381.6T patent/LT2991976T/lt unknown
- 2014-04-30 AU AU2014260011A patent/AU2014260011A1/en not_active Abandoned
- 2014-04-30 HU HUE14728381A patent/HUE034770T2/hu unknown
- 2014-04-30 EP EP17161076.9A patent/EP3199532A1/en not_active Withdrawn
- 2014-04-30 CA CA2910971A patent/CA2910971A1/en not_active Abandoned
- 2014-04-30 CN CN201810004591.8A patent/CN107935994A/zh active Pending
- 2014-04-30 WO PCT/US2014/036083 patent/WO2014179416A1/en not_active Ceased
- 2014-04-30 ES ES14728381.6T patent/ES2645944T3/es active Active
- 2014-04-30 KR KR1020157034184A patent/KR20160003228A/ko not_active Withdrawn
- 2014-04-30 TW TW103115643A patent/TW201536766A/zh unknown
- 2014-04-30 CN CN201480038438.7A patent/CN105377831B/zh not_active Expired - Fee Related
- 2014-04-30 EP EP14728381.6A patent/EP2991976B1/en active Active
- 2014-04-30 SI SI201430431T patent/SI2991976T1/sl unknown
- 2014-04-30 PT PT147283816T patent/PT2991976T/pt unknown
- 2014-04-30 DK DK14728381.6T patent/DK2991976T3/da active
- 2014-04-30 SG SG11201508836XA patent/SG11201508836XA/en unknown
- 2014-04-30 US US14/266,448 patent/US9067912B2/en not_active Expired - Fee Related
- 2014-04-30 NZ NZ628322A patent/NZ628322A/en not_active IP Right Cessation
- 2014-04-30 RU RU2015151359A patent/RU2015151359A/ru unknown
- 2014-04-30 MX MX2015015073A patent/MX363652B/es unknown
- 2014-04-30 JP JP2016511825A patent/JP6490055B2/ja not_active Expired - Fee Related
- 2014-04-30 PL PL14728381T patent/PL2991976T3/pl unknown
- 2014-04-30 RS RS20171105A patent/RS56565B1/sr unknown
-
2015
- 2015-06-10 US US14/736,146 patent/US9266858B2/en not_active Expired - Fee Related
- 2015-09-24 US US14/864,614 patent/US9303014B2/en not_active Expired - Fee Related
- 2015-10-27 PH PH12015502477A patent/PH12015502477A1/en unknown
-
2017
- 2017-02-13 AU AU2017200965A patent/AU2017200965A1/en not_active Abandoned
- 2017-10-26 CY CY20171101119T patent/CY1119525T1/el unknown
-
2018
- 2018-12-06 JP JP2018229189A patent/JP2019069958A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2015151359A (ru) | Синтез 3-(5-амино-2-метил-4-оксохиназолин-3(4н)-ил)пиперидин-2, 6-диона | |
| JP2016517886A5 (https=) | ||
| KR101342241B1 (ko) | 4-아미노-2-(2,6-디옥소피페리딘-3-일)이소인돌린-1,3-디온 화합물의 제조 방법 | |
| WO2024190464A1 (ja) | アクリル酸誘導体の製造方法 | |
| EP3233823B1 (en) | Processes for the preparation of a diarylthiohydantoin compound | |
| JP2018058860A (ja) | 置換された５−フルオロ−１ｈ−ピラゾロピリジン類を製造するための方法 | |
| JP2015531776A5 (https=) | ||
| RU2016123144A (ru) | Сложноэфирное хиральное соединение (n-замещенный имидазол)-карбоновой кислоты, содержащее простую эфирную боковую цепь, его получение и применение | |
| RU2018106948A (ru) | Способ получения замещенных производных 3-(2-анилино-1-циклогексил -1н-бензимидазол-5-ил)пропановой кислоты | |
| JP2019527228A5 (https=) | ||
| KR20170036677A (ko) | 3-(3-클로로-1h-피라졸-1-일)피리딘의 제조 방법 | |
| CA2906581A1 (en) | A method of preparing glucosylceramide synthase quinuclidine carbamate inhibitors, and thiazole intermediates | |
| JP2020528437A (ja) | アミノピリミジン誘導体の合成に有用な新規中間体、それを調製するためのプロセス、及びそれを使用してアミノピリミジン誘導体を調製するためのプロセス | |
| AU2013369473B2 (en) | Process for the preparation of 1-((1,3)dioxolan-4-ylmethyl)-1h-pyrazol-3-ylamine | |
| CN110526927B (zh) | 一种唑啉草酯的制备方法 | |
| CN102627648A (zh) | 一种西他列汀的制备方法 | |
| KR20150046285A (ko) | 옥사졸 화합물을 제조하는 방법 | |
| KR101713303B1 (ko) | 2ｈ-인다졸 유도체의 제조방법 | |
| KR102458638B1 (ko) | 메데토미딘의 합성에서 유용한 3-아릴부탄알과 같은 화합물의 제조 방법 | |
| RU2019106531A (ru) | Кристалл соли производного хиназолина | |
| ES2965478T3 (es) | Protodescarboxilación catalizada por metales de transición de derivados del ácido alfa-halo-acrílico | |
| WO2014128094A1 (en) | Asymmetric synthesis of a substituted pyrrolidine-2-carboxamide | |
| CN110078636B (zh) | 一种制备碘普罗胺中间体的方法 | |
| JP6425734B2 (ja) | Ｎ−ベンジル−２−（２−ニトロ−１ｈ−イミダゾール−１−イル）アセトアミドを得るための製造工程 | |
| JP2018135315A (ja) | ６−アミノ−２ｈ−１，４−ベンズオキサジン−３（４ｈ）−オン類の製造方法 |