ZA200605747B - Production method - Google Patents
Production method Download PDFInfo
- Publication number
- ZA200605747B ZA200605747B ZA200605747A ZA200605747A ZA200605747B ZA 200605747 B ZA200605747 B ZA 200605747B ZA 200605747 A ZA200605747 A ZA 200605747A ZA 200605747 A ZA200605747 A ZA 200605747A ZA 200605747 B ZA200605747 B ZA 200605747B
- Authority
- ZA
- South Africa
- Prior art keywords
- reaction
- process according
- solvent
- phenyl
- vii
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- NVZIFMAZKAYQJR-UHFFFAOYSA-N 3-(aminomethyl)-1,3-oxazolidin-2-one Chemical compound NCN1CCOC1=O NVZIFMAZKAYQJR-UHFFFAOYSA-N 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- WHRGBOXIIYUXEF-UHFFFAOYSA-N O=C(C1=CC=C[S+]1Cl)Cl Chemical compound O=C(C1=CC=C[S+]1Cl)Cl WHRGBOXIIYUXEF-UHFFFAOYSA-N 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- JKHRKKGVFCLUPM-UHFFFAOYSA-N CC1=C2C(C(=O)NC2=O)=CC=C1.O1C(NCC1)=O Chemical compound CC1=C2C(C(=O)NC2=O)=CC=C1.O1C(NCC1)=O JKHRKKGVFCLUPM-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- BMPDCQVRKDNUAP-UHFFFAOYSA-N 5-chlorothiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)S1 BMPDCQVRKDNUAP-UHFFFAOYSA-N 0.000 description 11
- DUILGEYLVHGSEE-ZETCQYMHSA-N 2-[[(2s)-oxiran-2-yl]methyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C[C@H]1CO1 DUILGEYLVHGSEE-ZETCQYMHSA-N 0.000 description 10
- DEXXSYVEWAYIGZ-LBPRGKRZSA-N 4-[4-[(5s)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]morpholin-3-one Chemical compound O=C1O[C@@H](CN)CN1C1=CC=C(N2C(COCC2)=O)C=C1 DEXXSYVEWAYIGZ-LBPRGKRZSA-N 0.000 description 10
- MHCRLDZZHOVFEE-UHFFFAOYSA-N 4-(4-aminophenyl)morpholin-3-one Chemical compound C1=CC(N)=CC=C1N1C(=O)COCC1 MHCRLDZZHOVFEE-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- -1 alkaline earth metal carbonates Chemical class 0.000 description 3
- 238000011097 chromatography purification Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- GCPHKTQMABHWPY-UHFFFAOYSA-N 3-chlorothiophene-2-carbonyl chloride Chemical compound ClC(=O)C=1SC=CC=1Cl GCPHKTQMABHWPY-UHFFFAOYSA-N 0.000 description 2
- TXSRBXVVEZQPHJ-UHFFFAOYSA-N 4-anilinomorpholin-3-one Chemical compound O=C1COCCN1NC1=CC=CC=C1 TXSRBXVVEZQPHJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- MKKGUXJPBITOKI-GFCCVEGCSA-N 4-[4-[[(2r)-3-amino-2-hydroxypropyl]amino]phenyl]morpholin-3-one Chemical compound C1=CC(NC[C@H](O)CN)=CC=C1N1C(=O)COCC1 MKKGUXJPBITOKI-GFCCVEGCSA-N 0.000 description 1
- KPLVWXBCSNCNJA-YFKPBYRVSA-N 5-chloro-n-[(2s)-2,3-dihydroxypropyl]thiophene-2-carboxamide Chemical compound OC[C@@H](O)CNC(=O)C1=CC=C(Cl)S1 KPLVWXBCSNCNJA-YFKPBYRVSA-N 0.000 description 1
- QZLSBOVWPHXCLT-UHFFFAOYSA-N 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)S1 QZLSBOVWPHXCLT-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 206010002388 Angina unstable Diseases 0.000 description 1
- 108010039209 Blood Coagulation Factors Proteins 0.000 description 1
- 102000015081 Blood Coagulation Factors Human genes 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000010378 Pulmonary Embolism Diseases 0.000 description 1
- 206010038563 Reocclusion Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 208000032109 Transient ischaemic attack Diseases 0.000 description 1
- 208000007814 Unstable Angina Diseases 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- VHINDKDACFDWPC-UHFFFAOYSA-N [O-]C(C1=CC=C[S+]1Cl)=O Chemical compound [O-]C(C1=CC=C[S+]1Cl)=O VHINDKDACFDWPC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- 239000003114 blood coagulation factor Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 208000010125 myocardial infarction Diseases 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
- 231100000614 poison Toxicity 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- 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
- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004002044A DE102004002044A1 (de) | 2004-01-15 | 2004-01-15 | Herstellverfahren |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200605747B true ZA200605747B (en) | 2007-10-31 |
Family
ID=34716548
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200605747A ZA200605747B (en) | 2004-01-15 | 2006-07-12 | Production method |
Country Status (33)
Country | Link |
---|---|
US (1) | US7351823B2 (es) |
EP (1) | EP1720866B1 (es) |
JP (2) | JP5311742B2 (es) |
KR (1) | KR20130004257A (es) |
CN (1) | CN1906191B (es) |
AR (1) | AR047389A1 (es) |
AT (1) | ATE518856T1 (es) |
AU (1) | AU2004313694B2 (es) |
BR (1) | BRPI0418405B8 (es) |
CA (1) | CA2553237C (es) |
CY (1) | CY1112565T1 (es) |
DE (1) | DE102004002044A1 (es) |
DK (1) | DK1720866T3 (es) |
EC (1) | ECSP066703A (es) |
ES (1) | ES2369140T3 (es) |
GT (1) | GT200400277A (es) |
HK (1) | HK1103722A1 (es) |
HN (1) | HN2005000016A (es) |
HR (1) | HRP20110796T1 (es) |
IL (1) | IL176767A (es) |
MA (1) | MA28290A1 (es) |
MY (1) | MY138944A (es) |
NO (1) | NO335553B1 (es) |
NZ (1) | NZ548506A (es) |
PE (1) | PE20050763A1 (es) |
PL (1) | PL1720866T3 (es) |
PT (1) | PT1720866E (es) |
RU (1) | RU2383540C2 (es) |
SI (1) | SI1720866T1 (es) |
TW (1) | TWI340137B (es) |
UY (1) | UY28718A1 (es) |
WO (1) | WO2005068456A1 (es) |
ZA (1) | ZA200605747B (es) |
Families Citing this family (81)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19962924A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
DE10129725A1 (de) | 2001-06-20 | 2003-01-02 | Bayer Ag | Kombinationstherapie substituierter Oxazolidinone |
DE10300111A1 (de) | 2003-01-07 | 2004-07-15 | Bayer Healthcare Ag | Verfahren zur Herstellung von 5-Chlor-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophencarboxamid |
DE10355461A1 (de) | 2003-11-27 | 2005-06-23 | Bayer Healthcare Ag | Verfahren zur Herstellung einer festen, oral applizierbaren pharmazeutischen Zusammensetzung |
DE102004062475A1 (de) * | 2004-12-24 | 2006-07-06 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit modifizierter Freisetzung |
EP1685841A1 (en) | 2005-01-31 | 2006-08-02 | Bayer Health Care Aktiengesellschaft | Prevention and treatment of thromboembolic disorders |
DE102005045518A1 (de) | 2005-09-23 | 2007-03-29 | Bayer Healthcare Ag | 2-Aminoethoxyessigsäure-Derivate und ihre Verwendung |
DE102005047564A1 (de) * | 2005-10-04 | 2007-05-31 | Bayer Healthcare Ag | Amorphe Form von 5-Chlor-N-({(5S)2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl)-methyl)-2-thiophencarboxamid |
DE102005047561A1 (de) | 2005-10-04 | 2007-04-05 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit schneller Wirkstofffreisetzung |
DE102005047558A1 (de) * | 2005-10-04 | 2008-02-07 | Bayer Healthcare Ag | Kombinationstherapie substituierter Oxazolidinone zur Prophylaxe und Behandlung von cerebralen Durchblutungsstörungen |
PL1934208T3 (pl) * | 2005-10-04 | 2011-09-30 | Bayer Ip Gmbh | Nowa polimorficzna postać 5-chloro-N-({ (5S)-2-okso-3-[4-( 3-okso-4-morfolinylo)-fenylo]-1,3-oksazolidyn-5-ylo}-metylo)-2-tiofenokarboksamidu |
DE102006007146A1 (de) | 2006-02-16 | 2007-08-23 | Bayer Healthcare Ag | Aminoacyl-Prodrugs |
DE102006039589A1 (de) * | 2006-08-24 | 2008-03-06 | Bayer Healthcare Ag | Aminoacyl-Prodrugs II |
DE102006051625A1 (de) * | 2006-11-02 | 2008-05-08 | Bayer Materialscience Ag | Kombinationstherapie substituierter Oxazolidinone |
DE102007028319A1 (de) * | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
DE102007028407A1 (de) * | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
WO2009018807A1 (de) * | 2007-08-06 | 2009-02-12 | Schebo Biotech Ag | Oxazolidinone als faktor xa- inhibitoren, verfahren zu ihrer herstellung und ihre verwendung in der therapie |
US8706950B2 (en) | 2008-03-01 | 2014-04-22 | Kabushiki Kaisha Toshiba | Memory system |
DE102008028071A1 (de) * | 2008-06-12 | 2009-12-17 | Bayer Schering Pharma Aktiengesellschaft | Neue Cokristall-Verbindung von Rivaroxaban und Malonsäure |
US20100168111A1 (en) * | 2008-12-31 | 2010-07-01 | Apotex Pharmachem Inc. | Polymorphic form of 5 chloro n {[(5s) 2 oxo 3 [4 (3 oxomorpholin 4 yl)phenyl]oxa-zolidin 5 yl]-methyl}thiophene 2 carboxamide |
US8435989B2 (en) * | 2009-04-28 | 2013-05-07 | Apotex Pharmachem Inc. | Processes for the preparation of rivaroxaban and intermediates thereof |
US7816355B1 (en) * | 2009-04-28 | 2010-10-19 | Apotex Pharmachem Inc | Processes for the preparation of rivaroxaban and intermediates thereof |
US8309547B2 (en) * | 2009-04-28 | 2012-11-13 | Apotex Pharmachem Inc. | Processes for the preparation of rivaroxaban and intermediates thereof |
WO2011012321A1 (en) | 2009-07-31 | 2011-02-03 | Krka, D.D., Novo Mesto | Processes for crystallization of rivaroxaban |
CN102822167A (zh) * | 2010-01-04 | 2012-12-12 | 埃南蒂亚有限公司 | 用于制备利伐沙班的方法及其中间体 |
DE102010028362A1 (de) | 2010-04-29 | 2011-11-03 | Bayer Schering Pharma Aktiengesellschaft | Herstellverfahren |
EP2388260A1 (de) * | 2010-05-21 | 2011-11-23 | Archimica GmbH | Herstellungsverfahren für einen Inhibitor eines Blutgerinnungsfaktors |
CN107021932A (zh) * | 2010-06-29 | 2017-08-08 | 欧美嘉股份有限公司 | 制备5‑左旋‑氨甲基‑3‑芳基‑2‑恶唑烷酮类的方法 |
EP2404920A1 (en) | 2010-07-06 | 2012-01-11 | Sandoz AG | Crystalline form of Rivaroxaban dihydrate |
US20130253187A1 (en) * | 2010-09-14 | 2013-09-26 | Medichem, S.A. | Process for Determining the Suitability for Distribution of a Batch of Thiophene-2-Carboxamide Derivative |
CZ2010714A3 (cs) * | 2010-09-30 | 2012-04-11 | Farmak, A. S. | Zpusob výroby 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morfolinyl)fenyl]-1,3oxazolidin-5-yl}methyl)-1H-isoindol-1,3(2H)-dionu ve vysoké optické cistote |
EP2630143B1 (en) | 2010-10-18 | 2017-11-29 | Apotex Pharmachem Inc. | Processes for the preparation of rivaroxaban and intermediates thereof |
MD4557C1 (ro) * | 2011-05-06 | 2018-10-31 | Egis Gyogysszegyar Nyilvanosan Mukodo Reszvenytarsasag | Procedeu de obţinere a rivaroxabanului şi un compus intermediar utilizat în acest procedeu |
WO2012156983A1 (en) * | 2011-05-16 | 2012-11-22 | Symed Labs Limited | Processes for the preparation of 5-chloro-n-({(5s)-2-oxo-3-[4-(3-oxo-4-morpholinyl) phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide |
ES2395304B1 (es) | 2011-05-20 | 2014-01-16 | Interquim, S.A. | Procedimiento de obtención de una tiofen-2-carboxamida. |
CN102250076A (zh) * | 2011-05-27 | 2011-11-23 | 横店集团家园化工有限公司 | 一种利伐沙班中间体及利伐沙班的制备方法 |
CN102827154B (zh) * | 2011-06-14 | 2015-04-22 | 上海科胜药物研发有限公司 | 一种合成利伐沙班中间体4-{4-[(5s)-5-(氨基甲基)-2-氧代-1,3-恶唑烷-3-基]苯基}吗啉-3-酮的方法 |
EP2753619A2 (en) | 2011-09-08 | 2014-07-16 | Cadila Healthcare Limited | Processes and intermediates for preparing rivaroxaban |
WO2013053739A1 (en) | 2011-10-10 | 2013-04-18 | Laboratorios Lesvi, S. L. | Process for preparing factor xa inhibitors |
WO2013121436A2 (en) * | 2012-02-06 | 2013-08-22 | Megafine Pharma (P) Ltd | A process for preparation of rivaroxaban and intermediates thereof |
CZ2012114A3 (cs) * | 2012-02-17 | 2013-02-20 | Zentiva, K.S. | Zpusob prípravy rivaroxabanu zalozený na úspore 1,1´ -karbonyldiimidazolu |
CN103288814B (zh) | 2012-02-24 | 2016-07-06 | 国药集团国瑞药业有限公司 | 一种利伐沙班中间体的制备方法 |
CN102659756A (zh) * | 2012-04-01 | 2012-09-12 | 南京哈柏医药科技有限公司 | 5-氯-2-酰氯噻吩的合成方法 |
US9562040B2 (en) | 2012-04-06 | 2017-02-07 | Indiana University Research And Technology Corporation | Processes for preparing Rivaroxaban |
ES2871811T3 (es) | 2012-05-02 | 2021-11-02 | Symed Labs Ltd | Proceso mejorado para preparar rivaroxabán utilizando intermedios novedosos |
CN102757424B (zh) * | 2012-07-09 | 2014-10-15 | 云南大学 | 2-苄基取代苯并呋喃—咪唑盐类化合物及其制备方法 |
CN102746288B (zh) * | 2012-07-24 | 2015-04-08 | 常州制药厂有限公司 | 一种抗凝血药及其关键中间体的制备方法 |
WO2014020458A1 (en) * | 2012-08-01 | 2014-02-06 | Alembic Pharmaceuticals Limited | Improved process for preparation of rivaroxaban |
CN102786516B (zh) * | 2012-08-21 | 2014-10-01 | 湖南师范大学 | 一种利伐沙班的合成方法 |
CN103833724A (zh) * | 2012-11-20 | 2014-06-04 | 上海医药工业研究院 | 一种5-氯噻吩-2-甲酰氯的制备方法 |
CN103864772A (zh) * | 2012-12-13 | 2014-06-18 | 北京京卫信康医药科技发展有限公司 | 一种利伐沙班及其中间体的制备方法 |
CN103864771A (zh) * | 2012-12-13 | 2014-06-18 | 北京京卫信康医药科技发展有限公司 | 一种利伐沙班的制备方法 |
WO2014096214A1 (en) * | 2012-12-21 | 2014-06-26 | Farma Grs, D.O.O. | A process for preparation of rivaroxaban |
HUE032850T2 (en) | 2012-12-26 | 2017-11-28 | Wanbury Ltd | Rivaroxaban intermediate and its preparation |
EP2897619A4 (en) | 2012-12-26 | 2016-08-17 | Wanbury Ltd | ALDEHYDE DERIVATIVE FROM SUBSTITUTED OXAZOLIDINONES |
US9663505B2 (en) | 2013-03-25 | 2017-05-30 | Glenmark Pharmaceuticals Limited | Process for the preparation of rivaroxaban |
CN104109158A (zh) * | 2013-04-16 | 2014-10-22 | 上海医药工业研究院 | 一种纯化利伐沙班的方法 |
CN103275061A (zh) * | 2013-06-04 | 2013-09-04 | 上海同昌生物医药科技有限公司 | 一种生产5-氯噻吩-2-羧酸的方法 |
CN103351385A (zh) * | 2013-06-28 | 2013-10-16 | 浙江燎原药业有限公司 | 一种利伐沙班中间体的制备方法 |
CN103709116B (zh) * | 2013-12-10 | 2015-09-23 | 四川大学 | 一种4-(4-烷氧羰氨基)苯基-3-吗啉酮的制备方法 |
CN103724336B (zh) * | 2013-12-24 | 2015-10-21 | 悦康药业集团有限公司 | 一种新型抗凝血药物的合成方法 |
IN2014MU00072A (es) | 2014-01-08 | 2015-08-21 | Wockhardt Ltd | |
WO2015111076A2 (en) | 2014-01-23 | 2015-07-30 | Symed Labs Limited | Improved processes for the preparation of highly pure rivaroxaban crystal modification i |
CN105085370B (zh) * | 2014-04-22 | 2017-04-12 | 北大方正集团有限公司 | (s)‑1‑卤代‑2‑[2‑(1,3‑二氧异吲哚)基]乙基氯甲酸酯及其制备方法 |
WO2015188787A1 (en) * | 2014-06-14 | 2015-12-17 | Sunshine Lake Pharma Co., Ltd. | Method for preparing oxazolidinone compound and intermediates thereof |
CN104086539A (zh) * | 2014-07-17 | 2014-10-08 | 天津炜捷制药有限公司 | 一种利伐沙班的制备方法 |
CN104211693B (zh) * | 2014-08-07 | 2017-02-22 | 成都百裕制药股份有限公司 | 一种利伐沙班晶型及其制备方法与用途 |
CN104211694A (zh) * | 2014-08-14 | 2014-12-17 | 广东东阳光药业有限公司 | 一种改进的制备Xa因子抑制剂的方法 |
US20170267669A1 (en) * | 2014-08-25 | 2017-09-21 | Cipla Limited | Process for the Preparation of Rivaroxaban |
EA034656B1 (ru) | 2014-10-22 | 2020-03-03 | Закляды Фармацеутычне Польфарма С.А | Способ получения полиморфа ривароксабана |
CN104807934B (zh) * | 2015-04-30 | 2017-01-18 | 成都百裕制药股份有限公司 | 异吲哚二酮类化合物的正相高效液相色谱检测方法 |
CN105130976A (zh) * | 2015-08-26 | 2015-12-09 | 浙江车头制药股份有限公司 | 一种利伐沙班中间体的合成方法 |
CN105440028B (zh) * | 2015-12-07 | 2018-03-13 | 石家庄康贺威药业有限公司 | 一种利伐沙班化合物及其制备方法 |
CN106008490B (zh) * | 2016-01-11 | 2019-01-04 | 南京生命能科技开发有限公司 | 一种利伐沙班的新晶体及其制备方法 |
CN106977507A (zh) * | 2017-04-21 | 2017-07-25 | 上海华源医药科技发展有限公司 | 一种利伐沙班的制备方法 |
CN109553611A (zh) * | 2017-09-23 | 2019-04-02 | 齐鲁制药有限公司 | 利伐沙班中间体的制备方法和用途 |
JP7205529B2 (ja) * | 2018-02-26 | 2023-01-17 | 住友化学株式会社 | オキサゾリジノン化合物の製造方法 |
JP7339754B2 (ja) * | 2019-03-27 | 2023-09-06 | ダイト株式会社 | 中間体の製造方法 |
CN112521380A (zh) * | 2020-12-14 | 2021-03-19 | 哈尔滨珍宝制药有限公司 | 一种利伐沙班中间体a的合成方法及其在制备利伐沙班中的应用 |
BR112023024807A2 (pt) * | 2021-05-28 | 2024-02-15 | Merck Sharp & Dohme Llc | Síntese de inibidor de btk e intermediários do mesmo |
EP4201933A1 (en) | 2021-12-23 | 2023-06-28 | Zaklady Farmaceutyczne Polpharma S.A. | Crystallisation process for rivaroxaban |
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DE19962924A1 (de) * | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
DE10129725A1 (de) * | 2001-06-20 | 2003-01-02 | Bayer Ag | Kombinationstherapie substituierter Oxazolidinone |
DE10300111A1 (de) * | 2003-01-07 | 2004-07-15 | Bayer Healthcare Ag | Verfahren zur Herstellung von 5-Chlor-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophencarboxamid |
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