BG61605B1 - Метод за получаване на формотерол и съединения от същатагрупа - Google Patents
Метод за получаване на формотерол и съединения от същатагрупа Download PDFInfo
- Publication number
- BG61605B1 BG61605B1 BG97576A BG9757693A BG61605B1 BG 61605 B1 BG61605 B1 BG 61605B1 BG 97576 A BG97576 A BG 97576A BG 9757693 A BG9757693 A BG 9757693A BG 61605 B1 BG61605 B1 BG 61605B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- compound
- formula
- straight
- solvent
- alkyl group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims description 17
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 title description 15
- 229960002848 formoterol Drugs 0.000 title description 15
- 239000012453 solvate Substances 0.000 claims abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 22
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 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 description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 7
- 239000002798 polar solvent Substances 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- 238000006722 reduction reaction Methods 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 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 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical compound [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- -1 3-formamido-4-hydroxy-α- [N- [1-methyl-2- (p-methoxyphenyl) ethyl] aminomethyl] -benzyl Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229940124630 bronchodilator Drugs 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RATSWNOMCHFQGJ-TUYNVFRMSA-N (e)-but-2-enedioic acid;n-[2-hydroxy-5-[(1s)-1-hydroxy-2-[[(2s)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]phenyl]formamide;dihydrate Chemical compound O.O.OC(=O)\C=C\C(O)=O.C1=CC(OC)=CC=C1C[C@H](C)NC[C@@H](O)C1=CC=C(O)C(NC=O)=C1.C1=CC(OC)=CC=C1C[C@H](C)NC[C@@H](O)C1=CC=C(O)C(NC=O)=C1 RATSWNOMCHFQGJ-TUYNVFRMSA-N 0.000 description 3
- MOGUBMMGIJLRHQ-UHFFFAOYSA-N 2-(3-nitro-4-phenylmethoxyphenyl)oxirane Chemical compound [O-][N+](=O)C1=CC(C2OC2)=CC=C1OCC1=CC=CC=C1 MOGUBMMGIJLRHQ-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000000168 bronchodilator agent Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 229960000193 formoterol fumarate Drugs 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000005932 reductive alkylation reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- FWPQURKYXIFBAR-WXXKFALUSA-N (e)-but-2-enedioate;[2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]-[1-(4-methoxyphenyl)propan-2-yl]-dimethylazanium Chemical compound [O-]C(=O)\C=C\C([O-])=O.C1=CC(OC)=CC=C1CC(C)[N+](C)(C)CC(O)C1=CC=C(O)C(NC=O)=C1.C1=CC(OC)=CC=C1CC(C)[N+](C)(C)CC(O)C1=CC=C(O)C(NC=O)=C1 FWPQURKYXIFBAR-WXXKFALUSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 150000001350 alkyl halides Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 229960003610 formoterol fumarate dihydrate Drugs 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 231100000037 inhalation toxicity test Toxicity 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000422 nocturnal effect Effects 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- NEGYEDYHPHMHGK-UHFFFAOYSA-N para-methoxyamphetamine Chemical compound COC1=CC=C(CC(C)N)C=C1 NEGYEDYHPHMHGK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
- Pyrrole Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9003057A SE9003057D0 (sv) | 1990-09-26 | 1990-09-26 | New process |
| PCT/SE1991/000643 WO1992005147A1 (en) | 1990-09-26 | 1991-09-25 | New process for preparing formoterol and related compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG97576A BG97576A (bg) | 1994-03-31 |
| BG61605B1 true BG61605B1 (bg) | 1998-01-30 |
Family
ID=20380456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG97576A BG61605B1 (bg) | 1990-09-26 | 1993-03-24 | Метод за получаване на формотерол и съединения от същатагрупа |
Country Status (28)
| Country | Link |
|---|---|
| EP (1) | EP0550612B1 (cs) |
| JP (1) | JP2801401B2 (cs) |
| KR (1) | KR0179639B1 (cs) |
| AT (1) | ATE134990T1 (cs) |
| AU (1) | AU652386B2 (cs) |
| BG (1) | BG61605B1 (cs) |
| CA (1) | CA2091343C (cs) |
| CZ (1) | CZ284256B6 (cs) |
| DE (1) | DE69117768T2 (cs) |
| DK (1) | DK0550612T3 (cs) |
| EE (1) | EE02979B1 (cs) |
| ES (1) | ES2084831T3 (cs) |
| FI (1) | FI111714B (cs) |
| GR (1) | GR3020134T3 (cs) |
| HK (1) | HK52297A (cs) |
| HU (1) | HU214054B (cs) |
| IE (1) | IE74387B1 (cs) |
| IS (1) | IS1684B (cs) |
| LT (1) | LT3813B (cs) |
| LV (1) | LV10770B (cs) |
| NO (1) | NO301709B1 (cs) |
| PL (1) | PL166434B1 (cs) |
| PT (1) | PT99051B (cs) |
| RU (1) | RU2079486C1 (cs) |
| SE (1) | SE9003057D0 (cs) |
| SG (1) | SG43150A1 (cs) |
| SK (1) | SK22793A3 (cs) |
| WO (1) | WO1992005147A1 (cs) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6299863B1 (en) | 1992-04-03 | 2001-10-09 | Sepracor Inc. | Aerosol formulations containing micronized optically pure (R,R) formoterol for bronchodilating therapy |
| US6866839B2 (en) | 1991-04-05 | 2005-03-15 | Sepracor Inc. | Methods and compositions for treating pulmonary disorders using optically pure (R,R)-formoterol |
| US5795564A (en) * | 1991-04-05 | 1998-08-18 | Sepracor, Inc. | Methods and compositions for treating pulmonary disorders using optically pure (R,R)-formoterol |
| US5629200A (en) * | 1993-11-18 | 1997-05-13 | Daicel Chemical Industries, Ltd. | Production of optically active 2-amino-1-phenylethanol derivatives by asymetrical assimilation |
| SE9404080L (sv) * | 1993-12-28 | 1995-06-29 | Ciba Geigy Ag | Förfarande för framställning av en optiskt ren enantiomer av formoterol |
| CA2271004C (en) * | 1996-11-11 | 2007-05-01 | Sepracor Inc. | Process for the preparation of optically pure isomers of formoterol |
| US6040344A (en) | 1996-11-11 | 2000-03-21 | Sepracor Inc. | Formoterol process |
| US6303145B2 (en) | 1999-05-10 | 2001-10-16 | Sepracor Inc. | (S,R) formoterol methods and compositions |
| AR028948A1 (es) | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
| DE10290563D2 (de) * | 2001-02-22 | 2004-04-29 | Universitaetsklinikum Charite | Mittel zur Hemmung von Tumorzellen |
| US6472563B1 (en) | 2001-11-09 | 2002-10-29 | Sepracor Inc. | Formoterol tartrate process and polymorph |
| TWI359675B (en) | 2003-07-10 | 2012-03-11 | Dey L P | Bronchodilating β-agonist compositions |
| TW200738634A (en) | 2005-08-02 | 2007-10-16 | Astrazeneca Ab | New salt |
| WO2008035380A2 (en) * | 2006-09-19 | 2008-03-27 | Natco Pharma Limited | An improved process for the preparation of high purity formoterol and its pharmaceutically acceptable salts |
| TW200825084A (en) | 2006-11-14 | 2008-06-16 | Astrazeneca Ab | New compounds 521 |
| AU2008320590A1 (en) * | 2007-10-29 | 2009-05-07 | Generics [Uk] Limited | Novel chromatography methods |
| JP4837800B2 (ja) | 2008-05-13 | 2011-12-14 | アストラゼネカ・アクチエボラーグ | ムスカリンｍ３受容体アンタゴニストとしてのキヌクリジン誘導体 |
| CN101921200B (zh) * | 2009-06-16 | 2014-01-15 | 上海医药工业研究院 | 一种n-苄基-1-(4-甲氧基苯基)-2-丙胺的制备方法 |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| CN115368250B (zh) * | 2022-09-02 | 2024-07-26 | 博诺康源(北京)药业科技有限公司 | 拆分福莫特罗手性中间体的方法 |
| CN117682969A (zh) * | 2023-07-31 | 2024-03-12 | 浙江理工大学 | 一种福莫特罗中间体的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2366625C2 (cs) * | 1972-02-05 | 1988-06-09 | Yamanouchi Pharmaceutical Co., Ltd., Tokio/Tokyo, Jp | |
| GB1468156A (en) * | 1973-07-19 | 1977-03-23 | Ici Ltd | Phenylethylamine derivatives |
| ES2005492A6 (es) | 1987-12-23 | 1989-03-01 | Lasa Lab | Procedimiento de obtencion de n-(2-hidroxi-5-(1-hidroxi-2((2- (4-metoxifenil)-1metiletil)amino)etil)fenil)foramida (i). |
-
1990
- 1990-09-26 SE SE9003057A patent/SE9003057D0/xx unknown
-
1991
- 1991-09-25 SG SG1996004479A patent/SG43150A1/en unknown
- 1991-09-25 DK DK91917624.8T patent/DK0550612T3/da active
- 1991-09-25 PT PT99051A patent/PT99051B/pt not_active IP Right Cessation
- 1991-09-25 JP JP3516242A patent/JP2801401B2/ja not_active Expired - Lifetime
- 1991-09-25 IS IS3756A patent/IS1684B/is unknown
- 1991-09-25 WO PCT/SE1991/000643 patent/WO1992005147A1/en active IP Right Grant
- 1991-09-25 DE DE69117768T patent/DE69117768T2/de not_active Expired - Lifetime
- 1991-09-25 AU AU86520/91A patent/AU652386B2/en not_active Expired
- 1991-09-25 RU RU9193005269A patent/RU2079486C1/ru active
- 1991-09-25 PL PL91298237A patent/PL166434B1/pl unknown
- 1991-09-25 EP EP91917624A patent/EP0550612B1/en not_active Expired - Lifetime
- 1991-09-25 HU HU9300867A patent/HU214054B/hu unknown
- 1991-09-25 ES ES91917624T patent/ES2084831T3/es not_active Expired - Lifetime
- 1991-09-25 AT AT91917624T patent/ATE134990T1/de not_active IP Right Cessation
- 1991-09-25 CZ CZ93442A patent/CZ284256B6/cs not_active IP Right Cessation
- 1991-09-25 CA CA002091343A patent/CA2091343C/en not_active Expired - Lifetime
- 1991-09-25 SK SK22793A patent/SK22793A3/sk unknown
- 1991-09-25 KR KR1019930700901A patent/KR0179639B1/ko not_active Expired - Lifetime
- 1991-09-26 IE IE337391A patent/IE74387B1/en not_active IP Right Cessation
-
1993
- 1993-03-23 NO NO931058A patent/NO301709B1/no not_active IP Right Cessation
- 1993-03-24 BG BG97576A patent/BG61605B1/bg unknown
- 1993-03-25 FI FI931333A patent/FI111714B/fi not_active IP Right Cessation
- 1993-08-10 LV LVP-93-1025A patent/LV10770B/en unknown
- 1993-12-30 LT LTIP1715A patent/LT3813B/lt not_active IP Right Cessation
-
1994
- 1994-11-23 EE EE9400425A patent/EE02979B1/xx unknown
-
1996
- 1996-05-31 GR GR960401514T patent/GR3020134T3/el unknown
-
1997
- 1997-04-24 HK HK52297A patent/HK52297A/en not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BG61605B1 (bg) | Метод за получаване на формотерол и съединения от същатагрупа | |
| US5434304A (en) | Process for preparing formoterol and related compounds | |
| FR2493848A2 (fr) | Nouveaux derives des nor-tropane et granatane, leur procede de preparation et leur application en therapeutique | |
| SU1597096A3 (ru) | Способ получени производных дифенилпропиламина или их фармакологически приемлемых солей | |
| HU228197B1 (en) | Stable salts of 3,3-diphenylpropylamines derivatives and preparation thereof | |
| HU188353B (en) | Process for producing new xanthine derivatives | |
| JP2852681B2 (ja) | ２―アミノ―７―ヒドロキシテトラリンカルボキシアルキルエーテル類およびその製造方法 | |
| US4131686A (en) | Novel benzylalcohol derivatives and processes for preparing the same | |
| Sletzinger et al. | Potent decarboxylase inhibitors. Analogs of methyldopa1 | |
| US4451473A (en) | 3,7-Diazabicyclo [3.3.1] nonanes having anti-arrhythmic activity | |
| FR2483929A1 (fr) | Nouvelles adenosines n6-substituees utiles comme medicaments antihypertenseurs, compositions therapeutiques et formes pharmaceutiques les contenant, et leur procede de preparation | |
| KR100224330B1 (ko) | 골관절 질환의 치료에 유용한 n-((4,5-디히드록시-및 4,5,8-트리히드록시-9,10-디히드로-9,10-디옥소-2-안트라센-일)카르보닐)아미노산 | |
| EP0074903A2 (fr) | Dérivés d'amino-2 tétrahydro-1,2,3,4 naphtalène, leur préparation et leur application en thérapeutique | |
| JPS6136830B2 (cs) | ||
| CA1063619A (fr) | Procede de preparation de nouveaux acides benzylamino alcanoiques et les produits qui en resultent | |
| EP0101633B1 (en) | Pyridinecarboxylic esters of dopamine and of its n-alkyl derivatives | |
| HU177107B (en) | Process for producing new 1-phenyl-ethanolamine derivatives of antyflogistic activity | |
| WO1999062865A1 (en) | Haloethyl-2-[ (2,6-dichlorophenyl) amino] phenylacetoxyacetate derivatives and their use as an intermediate to synthesize aceclofenac | |
| KR800000537B1 (ko) | 아미노-페닐-에탄올아민의 제조방법 | |
| EP0178073A1 (en) | amide compounds, process for preparing the same and pharmaceutical compositions containing the same | |
| FR2555580A1 (fr) | Nouveaux composes azabicycliques, procede pour les preparer et medicaments les contenant | |
| HU195204B (en) | Process for the diastereoselective reduction of 3-amino-1-benzoxepin-5/2/+/-ones | |
| GB2067195A (en) | 2-aminomethyl-6-halo-phenols their production and pharmaceutical composition containing them | |
| US3960944A (en) | 8-Carboxamide dibenzobicyclo(3.2.1)octadienes | |
| CS247575B1 (cs) | Deriváty 1-fenoxy-3-fenoxyethylamino-2-propanolu a způsob jejich přípravy |