MX2008015396A - Metodos para preparar derivados de acido glutamico y sus intermedios. - Google Patents
Metodos para preparar derivados de acido glutamico y sus intermedios.Info
- Publication number
- MX2008015396A MX2008015396A MX2008015396A MX2008015396A MX2008015396A MX 2008015396 A MX2008015396 A MX 2008015396A MX 2008015396 A MX2008015396 A MX 2008015396A MX 2008015396 A MX2008015396 A MX 2008015396A MX 2008015396 A MX2008015396 A MX 2008015396A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- formula
- alkyl
- aryl
- heteroaryl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 46
- 150000002306 glutamic acid derivatives Chemical class 0.000 title abstract description 8
- 239000000543 intermediate Substances 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 273
- 125000003118 aryl group Chemical group 0.000 claims description 76
- 150000003839 salts Chemical class 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- -1 isopropyl magnesium halide Chemical class 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 52
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 34
- IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 150000002902 organometallic compounds Chemical class 0.000 claims description 17
- DVROTRJNFMCILR-UHFFFAOYSA-N CC(C)[Zn] Chemical compound CC(C)[Zn] DVROTRJNFMCILR-UHFFFAOYSA-N 0.000 claims description 15
- FRLYMSHUDNORBC-UHFFFAOYSA-N diisopropylzinc Chemical compound [Zn+2].C[CH-]C.C[CH-]C FRLYMSHUDNORBC-UHFFFAOYSA-N 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 15
- 238000006434 Ritter amidation reaction Methods 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000006242 amine protecting group Chemical group 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 229960000583 acetic acid Drugs 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000002360 preparation method Methods 0.000 abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 38
- 239000002585 base Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 150000002431 hydrogen Chemical group 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
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- 238000011260 co-administration Methods 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 229910001868 water Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 102000005741 Metalloproteases Human genes 0.000 description 10
- 108010006035 Metalloproteases Proteins 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 125000002837 carbocyclic group Chemical group 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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- 238000005481 NMR spectroscopy Methods 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
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- 102000002274 Matrix Metalloproteinases Human genes 0.000 description 5
- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
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- 125000006413 ring segment Chemical group 0.000 description 5
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
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- NVTZVRJGHWXKET-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-methylpropan-1-ol Chemical compound CC(C)C(O)C1=CC=C(F)C=C1 NVTZVRJGHWXKET-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C07C233/13—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/10—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing rings other than six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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- C07—ORGANIC CHEMISTRY
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81029206P | 2006-06-02 | 2006-06-02 | |
| PCT/US2007/012814 WO2007143014A2 (en) | 2006-06-02 | 2007-05-31 | Methods for preparing glutamic acid derivatives and intermediates thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2008015396A true MX2008015396A (es) | 2008-12-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2008015396A MX2008015396A (es) | 2006-06-02 | 2007-05-31 | Metodos para preparar derivados de acido glutamico y sus intermedios. |
Country Status (20)
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| EP (1) | EP2024326A2 (enExample) |
| JP (1) | JP2009539766A (enExample) |
| KR (1) | KR20090016503A (enExample) |
| CN (1) | CN101460449A (enExample) |
| AR (1) | AR061420A1 (enExample) |
| AU (1) | AU2007254960A1 (enExample) |
| BR (1) | BRPI0712233A2 (enExample) |
| CA (1) | CA2653463A1 (enExample) |
| CR (1) | CR10475A (enExample) |
| EC (1) | ECSP088933A (enExample) |
| IL (1) | IL195513A0 (enExample) |
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| TW (1) | TW200808715A (enExample) |
| WO (1) | WO2007143014A2 (enExample) |
| ZA (1) | ZA200810201B (enExample) |
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| US20100216886A1 (en) * | 2006-11-09 | 2010-08-26 | Wyeth | Polymorphs of n2-(1,1'-biphenyl-4-ylcarbonyl)-n1-[2-(4-fluorophenyl)-1,1-dimethylethyl]-l-alpha-glutamine |
| EP2089012A2 (en) * | 2006-11-09 | 2009-08-19 | Wyeth | Polymorphs of n²-(1,1'- biphenyl- 4-ylcarbonyl)-n¹-[2-(4-fluorophenyl)-1,1-dimethylethyl]-l-alpha -glutamine |
| JP5499947B2 (ja) * | 2010-06-30 | 2014-05-21 | 日産化学工業株式会社 | ポリ(5−(メタ)アクリロイル−2−アザアダマンタン−n−オキシル)の製造方法 |
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| WO2007008994A2 (en) * | 2005-07-11 | 2007-01-18 | Wyeth | Glutamate aggrecanase inhibitors |
| KR20080058436A (ko) * | 2005-10-13 | 2008-06-25 | 와이어쓰 | 글루탐산 유도체의 제조 방법 |
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- 2007-05-31 RU RU2008146043/04A patent/RU2008146043A/ru not_active Application Discontinuation
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2008
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Also Published As
| Publication number | Publication date |
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| CA2653463A1 (en) | 2007-12-13 |
| KR20090016503A (ko) | 2009-02-13 |
| JP2009539766A (ja) | 2009-11-19 |
| IL195513A0 (en) | 2009-09-01 |
| WO2007143014A2 (en) | 2007-12-13 |
| US20080119670A1 (en) | 2008-05-22 |
| PA8728901A1 (es) | 2009-02-09 |
| ZA200810201B (en) | 2010-01-27 |
| EP2024326A2 (en) | 2009-02-18 |
| WO2007143014A3 (en) | 2008-01-24 |
| NO20084839L (no) | 2008-12-18 |
| PE20080312A1 (es) | 2008-05-14 |
| TW200808715A (en) | 2008-02-16 |
| ECSP088933A (es) | 2009-01-30 |
| CN101460449A (zh) | 2009-06-17 |
| AR061420A1 (es) | 2008-08-27 |
| AU2007254960A1 (en) | 2007-12-13 |
| CR10475A (es) | 2009-01-07 |
| BRPI0712233A2 (pt) | 2012-01-10 |
| RU2008146043A (ru) | 2010-07-20 |
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