KR20090045920A - 방향족 시클로프로판 에스테르 및 아미드의 화학적 제조 방법 - Google Patents
방향족 시클로프로판 에스테르 및 아미드의 화학적 제조 방법 Download PDFInfo
- Publication number
- KR20090045920A KR20090045920A KR1020097003039A KR20097003039A KR20090045920A KR 20090045920 A KR20090045920 A KR 20090045920A KR 1020097003039 A KR1020097003039 A KR 1020097003039A KR 20097003039 A KR20097003039 A KR 20097003039A KR 20090045920 A KR20090045920 A KR 20090045920A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- treating
- difluorophenyl
- base
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000002360 preparation method Methods 0.000 title claims description 10
- -1 aromatic cyclopropane esters Chemical class 0.000 title description 12
- 150000001408 amides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical group [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 2
- 239000012450 pharmaceutical intermediate Substances 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VMEDAWUIKFAFJQ-UHFFFAOYSA-N 2-chloro-1-(3,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C=C1F VMEDAWUIKFAFJQ-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 3
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 2
- QVUBIQNXHRPJKK-UHFFFAOYSA-N 2-(3,4-difluorophenyl)cyclopropan-1-amine Chemical compound NC1CC1C1=CC=C(F)C(F)=C1 QVUBIQNXHRPJKK-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 0 *OC([C@](C1)C1c(cc1)cc(F)c1F)=O Chemical compound *OC([C@](C1)C1c(cc1)cc(F)c1F)=O 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- HMTZHWXNXMXQBU-ONEGZZNKSA-N C/C=C/c(ccc(C(CCl)=[O]=C)c1)c1F Chemical compound C/C=C/c(ccc(C(CCl)=[O]=C)c1)c1F HMTZHWXNXMXQBU-ONEGZZNKSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910019093 NaOCl Inorganic materials 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- BDOLXPFAFMNDOK-UHFFFAOYSA-N oxazaborolidine Chemical class B1CCON1 BDOLXPFAFMNDOK-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/58—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
- C07D301/26—Y being hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0615619.4A GB0615619D0 (en) | 2006-08-05 | 2006-08-05 | Chemical process for preparation of intermediates |
| GB0615619.4 | 2006-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20090045920A true KR20090045920A (ko) | 2009-05-08 |
Family
ID=37027327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097003039A Ceased KR20090045920A (ko) | 2006-08-05 | 2007-08-02 | 방향족 시클로프로판 에스테르 및 아미드의 화학적 제조 방법 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US7863469B2 (enExample) |
| EP (1) | EP2049462A4 (enExample) |
| JP (1) | JP2010500343A (enExample) |
| KR (1) | KR20090045920A (enExample) |
| CN (1) | CN101495442A (enExample) |
| AR (1) | AR062148A1 (enExample) |
| AU (1) | AU2007282181B2 (enExample) |
| BR (1) | BRPI0714573A2 (enExample) |
| CA (1) | CA2658953A1 (enExample) |
| CL (1) | CL2007002267A1 (enExample) |
| GB (1) | GB0615619D0 (enExample) |
| IL (1) | IL196233A0 (enExample) |
| MX (1) | MX2009001020A (enExample) |
| MY (1) | MY147871A (enExample) |
| TW (1) | TW200812958A (enExample) |
| WO (1) | WO2008018822A1 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0615619D0 (en) * | 2006-08-05 | 2006-09-13 | Astrazeneca Ab | Chemical process for preparation of intermediates |
| GB0615620D0 (en) | 2006-08-05 | 2006-09-13 | Astrazeneca Ab | A process for the preparation of optically active intermediates |
| BRPI0918038B1 (pt) | 2008-09-09 | 2021-07-13 | Astrazeneca Ab | Processo para preparar um composto |
| CN102356075B (zh) * | 2009-01-23 | 2015-06-10 | 里格尔药品股份有限公司 | 抑制jak途径的组合物和方法 |
| AU2011244023A1 (en) | 2010-04-20 | 2012-10-25 | Actavis Group Ptc Ehf | Novel process for preparing phenylcyclopropylamine derivatives using novel intermediates |
| JP2013530209A (ja) | 2010-06-30 | 2013-07-25 | アクタビス・グループ・ピーティーシー・イーエイチエフ | フェニルシクロプロピルアミン誘導体の新規調製方法及びチカグレロルを調製するためのそれらの使用 |
| WO2012063126A2 (en) | 2010-11-09 | 2012-05-18 | Actavis Group Ptc Ehf | Improved processes for preparing pure (3ar,4s,6r,6as)-6-amino-2,2-dimethyltetrahdro-3ah-cyclopenta[d] [1,3]-dioxol-4-ol and its key starting material |
| CN103429576A (zh) | 2010-12-20 | 2013-12-04 | 阿特维斯集团公司 | 制备三唑并[4,5-d]嘧啶衍生物及其中间体的新方法 |
| US20140206867A1 (en) | 2011-06-15 | 2014-07-24 | Actavis Group Ptc Ehf | Process for Preparing Cyclopentylamine Derivatives and Intermediates Thereof |
| EP2589587A1 (en) | 2011-11-04 | 2013-05-08 | Chemo Ibérica, S.A. | Synthesis of nitrogen substituted cyclopropanes |
| EP2628721A1 (en) * | 2012-02-20 | 2013-08-21 | LEK Pharmaceuticals d.d. | Synthesis of 2-(3,4-difluorophenyl)cyclopropanecarboxylic acid |
| EP2644590A1 (en) | 2012-03-30 | 2013-10-02 | LEK Pharmaceuticals d.d. | Synthesis of 2-(3,4-difluorophenyl)cyclopropanamine derivatives and salts |
| WO2013144295A1 (en) | 2012-03-30 | 2013-10-03 | Sandoz Ag | Synthesis of 2-(3,4-difluorophenyl)cyclopropanamine derivatives and salts |
| EP2834247A4 (en) | 2012-04-05 | 2016-03-30 | Reddys Lab Ltd Dr | PREPARATION OF TICAGRELOR |
| CN102775314A (zh) * | 2012-08-03 | 2012-11-14 | 江苏富泽药业有限公司 | 一种反式-（1r,2s）-2-(3,4-二氟苯基)环丙胺的制备方法 |
| CN103664697B (zh) * | 2012-09-07 | 2016-12-21 | 博瑞生物医药（苏州）股份有限公司 | 用于制备芳香族环丙腈及环丙胺的化学方法 |
| CN102863341B (zh) * | 2012-10-22 | 2014-05-07 | 南通大学 | 一种（1r,2s）-2-芳基环丙胺衍生物的化学合成方法 |
| CN103073525B (zh) * | 2013-02-04 | 2015-01-28 | 北京科技大学 | 一种合成制备(s)-(3,4-二氟苯基)环氧己烷的方法 |
| CN103087011A (zh) * | 2013-02-04 | 2013-05-08 | 北京科技大学 | 一种水解动力学拆分制备(s)-3,4-二氟苯基环氧乙烷的方法 |
| WO2014206187A1 (zh) | 2013-06-24 | 2014-12-31 | 苏州明锐医药科技有限公司 | 替卡格雷及其中间体的制备方法 |
| CN104974017B (zh) * | 2014-04-09 | 2017-11-17 | 上海医药工业研究院 | (1r,2s)‑2‑(3,4‑二氟苯基)环丙胺·d‑扁桃酸盐的制备方法 |
| WO2015162630A1 (en) | 2014-04-25 | 2015-10-29 | Anlon Chemical Research Organization | Novel processes for preparing triazolo [4,5-d]- pyrimidines, including ticagrelor, vianew intermediates and new route of synthesis. |
| CN109970614B (zh) | 2014-05-15 | 2023-01-13 | 阵列生物制药公司 | 作为trka激酶抑制剂的化合物及其用途 |
| US10011605B2 (en) | 2014-06-18 | 2018-07-03 | Flamma Spa | Process for the preparation of triazolo[4,5-D] pyrimidine cyclopentane compounds |
| CN104326922B (zh) * | 2014-11-03 | 2016-08-17 | 成都百裕制药股份有限公司 | 替格瑞洛中间体(1r,2s)-2-(2,3-二氟苯基)环丙胺的制备方法 |
| TWI579259B (zh) * | 2014-12-17 | 2017-04-21 | 日名國際藥品有限公司 | 製備（１ｒ，２ｓ）－２－（３，４－二氟苯基）－３－ｒ取代－環丙胺的方法 |
| WO2016116942A1 (en) | 2015-01-20 | 2016-07-28 | Anlon Chemical Research Organization | Novel pharmaceutical compounds comprising ticagrelor with salts of aspirin |
| CN105671099A (zh) * | 2016-01-26 | 2016-06-15 | 中国科学院成都生物研究所 | 一种制备光学纯二氟苯基环氧乙烷的方法 |
| CN106854158B (zh) * | 2016-12-08 | 2019-06-14 | 淮阴工学院 | 一种替格瑞洛中间体的合成方法及其中间体 |
| CN106905182A (zh) * | 2017-01-12 | 2017-06-30 | 淮阴工学院 | 一种替格瑞洛中间体的合成方法及其中间体 |
| CN107118141B (zh) * | 2017-04-18 | 2018-11-30 | 淮阴工学院 | 一种替格瑞洛中间体的合成方法及其中间体 |
| CN107686447A (zh) * | 2017-08-25 | 2018-02-13 | 许昌恒生制药有限公司 | 一种替格瑞洛中间体的制备方法 |
| CN108083997A (zh) * | 2017-11-14 | 2018-05-29 | 南通常佑药业科技有限公司 | 一种手性芳基环丙胺衍生物的制备方法 |
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| CN110437092B (zh) * | 2019-07-11 | 2022-06-10 | 泓博智源(开原)药业有限公司 | 一种替格瑞洛关键中间体芳族环丙烷酰胺的制备方法 |
| CN111233673B (zh) * | 2020-02-26 | 2022-08-16 | 苏州元兴生物医药有限公司 | 一种手性芳香族环丙胺及其盐的制备方法及所用中间体 |
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| DE3546372A1 (de) * | 1985-12-31 | 1987-07-02 | Basf Ag | Neue phenylacetaldehyde und verfahren zur herstellung von phenylacetaldehyden |
| DE3729226A1 (de) * | 1987-09-02 | 1989-03-23 | Basf Ag | Verfahren zur herstellung von phenylsubstituierten epoxiden |
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| EP0611826B1 (en) * | 1993-02-15 | 2003-05-02 | Daicel Chemical Industries, Ltd. | Processes for production of optically active epoxides |
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| DE19523868A1 (de) | 1995-06-30 | 1997-01-02 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Cyclopropanamin |
| DE19547635A1 (de) * | 1995-12-20 | 1997-06-26 | Bayer Ag | Verfahren zur Herstellung von Cyclopropancarbonsäureamiden |
| TWI290549B (en) * | 2000-06-02 | 2007-12-01 | Astrazeneca Ab | Process for the preparation of cyclopropyl carboxylic acid ester and derivatives |
| GB0013488D0 (en) * | 2000-06-02 | 2000-07-26 | Astrazeneca Ab | Chemical compound |
| US6552217B2 (en) * | 2000-08-01 | 2003-04-22 | Eastman Chemical Company | Process for the preparation of alkyl 1-methylcyclopropanecarboxylate |
| US6683216B1 (en) * | 2002-11-06 | 2004-01-27 | Eastman Chemical Company | Continuous process for the preparation of amines |
| GB0615619D0 (en) * | 2006-08-05 | 2006-09-13 | Astrazeneca Ab | Chemical process for preparation of intermediates |
| GB0615620D0 (en) * | 2006-08-05 | 2006-09-13 | Astrazeneca Ab | A process for the preparation of optically active intermediates |
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2006
- 2006-08-05 GB GBGB0615619.4A patent/GB0615619D0/en not_active Ceased
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2007
- 2007-07-27 TW TW096127556A patent/TW200812958A/zh unknown
- 2007-07-30 AR ARP070103364A patent/AR062148A1/es not_active Application Discontinuation
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- 2007-08-02 AU AU2007282181A patent/AU2007282181B2/en not_active Ceased
- 2007-08-02 BR BRPI0714573-0A patent/BRPI0714573A2/pt not_active IP Right Cessation
- 2007-08-02 WO PCT/SE2007/000706 patent/WO2008018822A1/en not_active Ceased
- 2007-08-02 KR KR1020097003039A patent/KR20090045920A/ko not_active Ceased
- 2007-08-02 EP EP07794102A patent/EP2049462A4/en not_active Withdrawn
- 2007-08-02 CA CA002658953A patent/CA2658953A1/en not_active Abandoned
- 2007-08-02 CN CNA2007800287758A patent/CN101495442A/zh active Pending
- 2007-08-02 MX MX2009001020A patent/MX2009001020A/es active IP Right Grant
- 2007-08-02 MY MYPI20090411A patent/MY147871A/en unknown
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| EP2049462A4 (en) | 2012-06-13 |
| IL196233A0 (en) | 2009-09-22 |
| TW200812958A (en) | 2008-03-16 |
| JP2010500343A (ja) | 2010-01-07 |
| AU2007282181B2 (en) | 2012-04-19 |
| WO2008018822A1 (en) | 2008-02-14 |
| US20080132719A1 (en) | 2008-06-05 |
| CL2007002267A1 (es) | 2008-04-04 |
| EP2049462A1 (en) | 2009-04-22 |
| MY147871A (en) | 2013-01-31 |
| MX2009001020A (es) | 2009-02-05 |
| AR062148A1 (es) | 2008-10-15 |
| CA2658953A1 (en) | 2008-02-14 |
| BRPI0714573A2 (pt) | 2013-06-04 |
| CN101495442A (zh) | 2009-07-29 |
| GB0615619D0 (en) | 2006-09-13 |
| US20110137056A1 (en) | 2011-06-09 |
| US7863469B2 (en) | 2011-01-04 |
| AU2007282181A1 (en) | 2008-02-14 |
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