CS221845B2 - Method of making the ethanolamine derivatives - Google Patents
Method of making the ethanolamine derivatives Download PDFInfo
- Publication number
- CS221845B2 CS221845B2 CS815265A CS526581A CS221845B2 CS 221845 B2 CS221845 B2 CS 221845B2 CS 815265 A CS815265 A CS 815265A CS 526581 A CS526581 A CS 526581A CS 221845 B2 CS221845 B2 CS 221845B2
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- Czechoslovakia
- Prior art keywords
- formula
- compound
- hydrogen
- group
- sup
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 150000002169 ethanolamines Chemical class 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 149
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 230000008569 process Effects 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 230000002829 reductive effect Effects 0.000 claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- -1 benzylthio Chemical group 0.000 claims description 17
- 239000007858 starting material Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 1
- 210000005069 ears Anatomy 0.000 claims 1
- 235000013399 edible fruits Nutrition 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000013049 sediment Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 34
- 230000009471 action Effects 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 9
- 239000000543 intermediate Substances 0.000 abstract description 4
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 73
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 229960000195 terbutaline Drugs 0.000 description 39
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 38
- 210000002966 serum Anatomy 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000004480 active ingredient Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 239000003826 tablet Substances 0.000 description 12
- 239000008194 pharmaceutical composition Substances 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
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- 241000282472 Canis lupus familiaris Species 0.000 description 8
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 229940122601 Esterase inhibitor Drugs 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
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- 239000012071 phase Substances 0.000 description 4
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
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- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 241000283011 Rangifer Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- WKHOPHIMYDJVSA-UHFFFAOYSA-N [3-[2-(tert-butylamino)-1-hydroxyethyl]-5-(2-methylpropanoyloxy)phenyl] 2-methylpropanoate Chemical compound CC(C)C(=O)OC1=CC(OC(=O)C(C)C)=CC(C(O)CNC(C)(C)C)=C1 WKHOPHIMYDJVSA-UHFFFAOYSA-N 0.000 description 2
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- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
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- 239000004922 lacquer Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000009115 maintenance therapy Methods 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
- DLSOILHAKCBARI-UHFFFAOYSA-N n-benzyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NCC1=CC=CC=C1 DLSOILHAKCBARI-UHFFFAOYSA-N 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- QNPQIGJHCPFYRS-UHFFFAOYSA-N phosphoric acid;n-propan-2-ylpropan-2-amine Chemical compound OP(O)(O)=O.CC(C)NC(C)C QNPQIGJHCPFYRS-UHFFFAOYSA-N 0.000 description 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/34—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton and at least one hydroxy group bound to another carbon atom of the carbon skeleton
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (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)
- Steroid Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Luminescent Compositions (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8022439 | 1980-07-09 | ||
| GB8116441 | 1981-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS221845B2 true CS221845B2 (en) | 1983-04-29 |
Family
ID=26276161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS815265A CS221845B2 (en) | 1980-07-09 | 1981-07-08 | Method of making the ethanolamine derivatives |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US4419364A (en, 2012) |
| EP (1) | EP0043807B1 (en, 2012) |
| KR (3) | KR850000301B1 (en, 2012) |
| AT (1) | ATE7689T1 (en, 2012) |
| AU (1) | AU539976B2 (en, 2012) |
| CA (1) | CA1180021A (en, 2012) |
| CS (1) | CS221845B2 (en, 2012) |
| CY (1) | CY1273A (en, 2012) |
| DD (1) | DD202001A5 (en, 2012) |
| DE (1) | DE3163871D1 (en, 2012) |
| DK (1) | DK157678C (en, 2012) |
| ES (3) | ES503768A0 (en, 2012) |
| FI (1) | FI73666C (en, 2012) |
| GR (1) | GR74291B (en, 2012) |
| HK (1) | HK5385A (en, 2012) |
| HU (2) | HU187611B (en, 2012) |
| IE (1) | IE51373B1 (en, 2012) |
| IS (1) | IS1262B6 (en, 2012) |
| LU (1) | LU88304I2 (en, 2012) |
| MX (1) | MX9203239A (en, 2012) |
| MY (1) | MY8700026A (en, 2012) |
| NO (2) | NO152130C (en, 2012) |
| NZ (1) | NZ197628A (en, 2012) |
| PH (2) | PH16535A (en, 2012) |
| PL (1) | PL128513B1 (en, 2012) |
| PT (1) | PT73336B (en, 2012) |
| SG (1) | SG79784G (en, 2012) |
| SU (1) | SU1128830A3 (en, 2012) |
| YU (3) | YU42116B (en, 2012) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8904064D0 (sv) * | 1989-12-01 | 1989-12-01 | Astra Ab | Improved method of preparing an intermediate for the manufacture of bambuterol |
| SE9000948D0 (sv) * | 1990-03-16 | 1990-03-16 | Draco Ab | New use |
| US5830422A (en) * | 1995-06-23 | 1998-11-03 | Ormiston Mining And Smelting Co. Ltd. | Method for production of sodium bicarbonate, sodium carbonate and ammonium sulfate from sodium sulfate |
| WO1997026871A1 (en) * | 1996-01-29 | 1997-07-31 | Savor, Evelyn | Method of treating undesired uterine contractions using optically pure r- or rr-isomers of adrenergic beta-2 agonists |
| SE9604752D0 (sv) * | 1996-12-20 | 1996-12-20 | Astra Ab | Formulation and use |
| KR20030085658A (ko) * | 2002-04-30 | 2003-11-07 | 한올제약주식회사 | 밤부테롤의 개선된 합성방법 |
| US7495028B2 (en) * | 2002-08-08 | 2009-02-24 | Wen Tan | R-bambuterol, its preparation and therapeutic uses |
| WO2004014290A2 (en) * | 2002-08-08 | 2004-02-19 | Cheng J L | R-bambuterol, its preparation and therapeutic uses |
| CA2537185A1 (en) * | 2003-08-29 | 2005-03-10 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type-iv |
| EP1694655A2 (en) * | 2003-11-26 | 2006-08-30 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
| WO2006081986A1 (en) * | 2005-02-07 | 2006-08-10 | F.Hoffmann-La Roche Ag | Bambuterol and integrin inhibitor combination |
| WO2007031838A1 (en) | 2005-09-16 | 2007-03-22 | Ranbaxy Laboratories Limited | Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors |
| JP2009512676A (ja) | 2005-10-19 | 2009-03-26 | ランバクシー ラボラトリーズ リミテッド | ムスカリン性受容体アンタゴニストの医薬組成物 |
| US20090054382A1 (en) * | 2005-10-19 | 2009-02-26 | Abhijit Ray | Compositions of phosphodiesterase type iv inhibitors |
| EP2322507A1 (en) | 2006-08-22 | 2011-05-18 | Ranbaxy Laboratories Limited | Matrix metalloproteinase inhibitors |
| US20100029728A1 (en) * | 2006-09-22 | 2010-02-04 | Ranbaxy Laboratories Limited | Phosphodiesterase inhibitors |
| AU2007298549A1 (en) * | 2006-09-22 | 2008-03-27 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type-IV |
| EP1958947A1 (en) | 2007-02-15 | 2008-08-20 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type 4 |
| CN103497185A (zh) * | 2007-03-14 | 2014-01-08 | 兰贝克赛实验室有限公司 | 用作磷酸二酯酶抑制剂的吡唑并(3,4-b)吡啶衍生物 |
| EP2124943A1 (en) * | 2007-03-14 | 2009-12-02 | Ranbaxy Laboratories Limited | Pyrazolo [3, 4-b]pyridine derivatives as phosphodiesterase inhibitors |
| EP2111861A1 (en) | 2008-04-21 | 2009-10-28 | Ranbaxy Laboratories Limited | Compositions of phosphodiesterase type IV inhibitors |
| PH12013500198A1 (en) | 2010-07-30 | 2013-03-11 | Ranbaxy Laboratories Ltd | Matrix metalloproteinase inhibitors |
| JP2013540754A (ja) | 2010-09-24 | 2013-11-07 | ランバクシー ラボラトリーズ リミテッド | マトリックスメタロプロテイナーゼ阻害剤 |
| AU2013353723B2 (en) | 2012-12-03 | 2018-02-22 | Pfizer Inc. | Novel selective androgen receptor modulators |
| WO2014108449A1 (en) | 2013-01-08 | 2014-07-17 | Atrogi Ab | A screening method, a kit, a method of treatment and a compound for use in a method of treatment |
| CN104557614B (zh) * | 2014-12-15 | 2017-01-04 | 广东东阳光药业有限公司 | 一种胺的还原方法 |
| CN105622461B (zh) * | 2016-01-29 | 2018-06-19 | 华南理工大学 | 一种化合物及其制备方法与应用 |
| CN105859589B (zh) * | 2016-04-05 | 2018-09-28 | 深圳市康立生生物科技有限公司 | 一种制备班布特罗杂质c的方法 |
| GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714740D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| CN109942462B (zh) * | 2019-03-06 | 2022-01-14 | 宏冠生物药业有限公司 | 一种盐酸班布特罗的合成工艺 |
| GB201903832D0 (en) | 2019-03-20 | 2019-05-01 | Atrogi Ab | New compounds and methods |
| GB202205895D0 (en) | 2022-04-22 | 2022-06-08 | Atrogi Ab | New medical uses |
| CN120583945A (zh) | 2023-01-20 | 2025-09-02 | 阿托基公司 | 用于治疗或预防肌肉消耗的β2-肾上腺素能受体激动剂 |
| GB202302225D0 (en) | 2023-02-16 | 2023-04-05 | Atrogi Ab | New medical uses |
| GB202303229D0 (en) | 2023-03-06 | 2023-04-19 | Atrogi Ab | New medical uses |
| CN117586152A (zh) * | 2023-11-23 | 2024-02-23 | 黑龙江乌苏里江制药有限公司 | 一种盐酸班布特罗的制备方法 |
| GB202403169D0 (en) | 2024-03-05 | 2024-04-17 | Atrogi Ab | New medical uses |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE178032C1 (en, 2012) | 1961-01-01 | |||
| DE1643488U (de) | 1949-11-28 | 1952-09-11 | G E Hilge Fa | Brutgeraet. |
| DK85789C (da) | 1955-07-05 | 1958-06-30 | Cilag Ag | Fremgangsmåde til fremstilling af d,1- eller 1-isopropyl-aminometyl-(3,4-dihydroksy-fenyl)-karbinol eller salte deraf. |
| DE1768167U (de) | 1958-04-02 | 1958-06-04 | Artur O Herrmann | Warngeraet bei strassenhindernissen. |
| DE1275069B (de) | 1960-02-15 | 1968-08-14 | Boehringer Sohn Ingelheim | 1-(3', 5'-Dihydroxyphenyl)-1-hydroxy-2-isopropylaminoalkane und Verfahren zu ihrer Herstellung |
| NL282274A (en, 2012) | 1961-09-14 | |||
| FR1324857A (fr) * | 1962-06-14 | 1963-04-19 | Chemie Linz Ag | Procédé pour la préparation de dérivés de la phényléthanolamine |
| GB1141606A (en) | 1965-04-12 | 1969-01-29 | Rech S Et D Applic Scient Et M | Improvements in alkyl ethers of substituted phenylaminoethanols |
| DE1543372A1 (de) | 1966-10-18 | 1971-04-01 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von o-substituierten 3,4-Dioxyphenylalkanolaminen |
| US3937838A (en) * | 1966-10-19 | 1976-02-10 | Aktiebolaget Draco | Orally active bronchospasmolytic compounds and their preparation |
| NO132866C (en, 2012) | 1966-10-19 | 1976-01-21 | Draco Ab | |
| SE358633B (en, 2012) | 1966-10-19 | 1973-08-06 | Draco Ab | |
| SE335359B (en, 2012) | 1966-10-19 | 1971-05-24 | Draco Ab | |
| FR6087M (en, 2012) | 1967-01-10 | 1968-06-04 | ||
| SE369299B (en, 2012) | 1967-10-18 | 1974-08-19 | Draco Ab | |
| SE338324B (en, 2012) | 1967-12-19 | 1971-09-06 | Haessle Ab | |
| GB1298771A (en) | 1969-04-01 | 1972-12-06 | Sterling Drug Inc | Carboxylic esters of hydroxyphenylalkanolamines |
| AT294046B (de) | 1969-07-08 | 1971-11-10 | Chemie Linz Ag | Verfahren zur Herstellung des N,N'-Bis[2-(3',4'-dihydroxyphenyl)-2-hydroxyäthyl]-hexamethylendiamins, seiner optisch aktiven Formen und der Salze derselben |
| US3657319A (en) * | 1970-05-05 | 1972-04-18 | Smith Kline French Lab | Alpha-aminoalkyl-4-hydroxy-3-carboalkoxyaminobenzyl alcohols |
| NO126437B (en, 2012) | 1970-08-05 | 1973-02-05 | Draco Ab | |
| NL7112938A (en, 2012) | 1970-09-30 | 1972-04-05 | ||
| CH550771A (de) | 1970-10-30 | 1974-06-28 | Hoffmann La Roche | Verfahren zur herstellung von phenaethylaminderivaten. |
| US3876679A (en) | 1970-12-09 | 1975-04-08 | Aldrich Chem Co Inc | Di-substituted phenethylcarbamic acid esters |
| FI55988C (fi) | 1971-10-19 | 1979-11-12 | Klinge Co Chem Pharm Fab | Foerfarande foer framstaellning av terapeutiskt anvaendbara o-acylfenoletanolaminer |
| US4011258A (en) | 1973-06-21 | 1977-03-08 | Aktiebolaget Draco | Orally active bronchospasmolytic compounds |
| FI56673C (fi) | 1974-03-29 | 1981-02-04 | Huhtamaeki Yhthymae Oy | Nytt foerfarande foer framstaellning av alfa-tert-bytylaminometyl-4-hydroxy-m-xylen-alfa1 alfa3-diol |
| JPS556625B2 (en, 2012) | 1974-05-16 | 1980-02-18 | ||
| US4063025A (en) * | 1975-02-05 | 1977-12-13 | Yamanouchi Pharmaceutical Co., Ltd. | 4-Substituted amino-α-aminomethylbenzyl alcohol derivatives |
| SE7510988L (sv) | 1975-10-01 | 1977-04-02 | Draco Ab | Nya farmaceutiskt aktiva foreningar |
| DE2710997C3 (de) * | 1977-03-14 | 1980-08-14 | Dr. Karl Thomae Gmbh, 7950 Biberach | 4-Alkoxy carbonylamino-phenyläthanolamine, deren Herstellung und deren Verwendung als Arzneimittel |
-
1981
- 1981-06-30 EP EP81850117A patent/EP0043807B1/en not_active Expired
- 1981-06-30 DE DE8181850117T patent/DE3163871D1/de not_active Expired
- 1981-06-30 CY CY1273A patent/CY1273A/xx unknown
- 1981-06-30 AT AT81850117T patent/ATE7689T1/de active
- 1981-07-01 US US06/279,672 patent/US4419364A/en not_active Expired - Lifetime
- 1981-07-07 IE IE1522/81A patent/IE51373B1/en not_active IP Right Cessation
- 1981-07-07 PH PH25872A patent/PH16535A/en unknown
- 1981-07-07 NZ NZ197628A patent/NZ197628A/en unknown
- 1981-07-07 NO NO812311A patent/NO152130C/no unknown
- 1981-07-07 AU AU72618/81A patent/AU539976B2/en not_active Expired
- 1981-07-08 CS CS815265A patent/CS221845B2/cs unknown
- 1981-07-08 CA CA000381360A patent/CA1180021A/en not_active Expired
- 1981-07-08 PL PL1981232108A patent/PL128513B1/pl unknown
- 1981-07-08 SU SU813308249A patent/SU1128830A3/ru active
- 1981-07-08 IS IS2657A patent/IS1262B6/is unknown
- 1981-07-08 ES ES503768A patent/ES503768A0/es active Granted
- 1981-07-08 HU HU813788A patent/HU187611B/hu unknown
- 1981-07-08 DK DK303481A patent/DK157678C/da active
- 1981-07-08 PT PT73336A patent/PT73336B/pt unknown
- 1981-07-08 HU HU811986A patent/HU184959B/hu unknown
- 1981-07-08 FI FI812158A patent/FI73666C/fi not_active IP Right Cessation
- 1981-07-09 KR KR1019810002490A patent/KR850000301B1/ko not_active Expired
- 1981-07-09 DD DD81231626A patent/DD202001A5/de unknown
- 1981-07-09 YU YU1704/81A patent/YU42116B/xx unknown
- 1981-07-09 GR GR65453A patent/GR74291B/el unknown
-
1982
- 1982-06-15 ES ES513109A patent/ES8304534A1/es not_active Expired
- 1982-06-15 ES ES513108A patent/ES8304072A1/es not_active Expired
- 1982-07-06 US US06/395,650 patent/US4451663A/en not_active Expired - Lifetime
- 1982-07-23 PH PH27617A patent/PH19447A/en unknown
-
1983
- 1983-04-15 YU YU864/83A patent/YU43169B/xx unknown
- 1983-04-15 YU YU863/83A patent/YU43168B/xx unknown
-
1984
- 1984-09-26 KR KR1019840005925A patent/KR850000871B1/ko not_active Expired
- 1984-09-26 KR KR1019840005924A patent/KR850000870B1/ko not_active Expired
- 1984-11-09 SG SG797/84A patent/SG79784G/en unknown
-
1985
- 1985-01-17 HK HK53/85A patent/HK5385A/en not_active IP Right Cessation
-
1987
- 1987-12-30 MY MY26/87A patent/MY8700026A/xx unknown
-
1992
- 1992-06-24 MX MX9203239A patent/MX9203239A/es unknown
-
1993
- 1993-06-16 LU LU88304C patent/LU88304I2/fr unknown
-
1996
- 1996-06-27 NO NO1996008C patent/NO1996008I1/no unknown
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