CH634820A5 - Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. - Google Patents
Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. Download PDFInfo
- Publication number
- CH634820A5 CH634820A5 CH184777A CH184777A CH634820A5 CH 634820 A5 CH634820 A5 CH 634820A5 CH 184777 A CH184777 A CH 184777A CH 184777 A CH184777 A CH 184777A CH 634820 A5 CH634820 A5 CH 634820A5
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogen
- hydroxy
- hydroxyethylamino
- alkyl
- alkoxy
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 10
- 239000002253 acid Substances 0.000 title claims description 8
- UNARAUMROPGXGK-UHFFFAOYSA-N 1-[(2-hydroxy-2-phenylethyl)amino]-3-phenoxypropan-2-ol Chemical class C=1C=CC=CC=1OCC(O)CNCC(O)C1=CC=CC=C1 UNARAUMROPGXGK-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 hydroxy, amino Chemical group 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
- 125000005002 aryl methyl group Chemical group 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 9
- 150000002431 hydrogen Chemical group 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NVLNRWHDHUYMJM-UHFFFAOYSA-N 1-(benzylamino)-3-(4-methylphenoxy)propan-2-ol Chemical compound C1=CC(C)=CC=C1OCC(O)CNCC1=CC=CC=C1 NVLNRWHDHUYMJM-UHFFFAOYSA-N 0.000 description 1
- MTDSMQMSFFLKLG-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)oxirane Chemical compound C=1C=CC=CC=1COC(C=1)=CC=CC=1C1CO1 MTDSMQMSFFLKLG-UHFFFAOYSA-N 0.000 description 1
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 1
- HATFHPNOJRAXGH-UHFFFAOYSA-N 2-[benzyl-[2-hydroxy-3-(3-methylphenoxy)propyl]amino]-1-(4-phenylmethoxyphenyl)ethanone Chemical compound CC1=CC=CC(OCC(O)CN(CC(=O)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)CC=2C=CC=CC=2)=C1 HATFHPNOJRAXGH-UHFFFAOYSA-N 0.000 description 1
- IAPCKPXQFYWNDN-UHFFFAOYSA-N 2-bromo-1-(4-phenylmethoxyphenyl)ethanone Chemical compound C1=CC(C(=O)CBr)=CC=C1OCC1=CC=CC=C1 IAPCKPXQFYWNDN-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000005596 alkyl carboxamido group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 239000002371 cardiac agent Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 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 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
Classifications
-
- 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
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
-
- 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
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07C233/16—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 singly-bound oxygen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762606140 DE2606140A1 (de) | 1976-02-17 | 1976-02-17 | Neue derivate des 2-phenyl-2-hydroxyaethylamins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH634820A5 true CH634820A5 (en) | 1983-02-28 |
Family
ID=5970017
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH184777A CH634820A5 (en) | 1976-02-17 | 1977-02-15 | Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. |
| CH550381A CH634821A5 (en) | 1976-02-17 | 1981-08-26 | Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. |
| CH550481A CH634822A5 (en) | 1976-02-17 | 1981-08-26 | Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. |
| CH357282A CH635569A5 (en) | 1976-02-17 | 1982-06-09 | Process for preparing novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH550381A CH634821A5 (en) | 1976-02-17 | 1981-08-26 | Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. |
| CH550481A CH634822A5 (en) | 1976-02-17 | 1981-08-26 | Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. |
| CH357282A CH635569A5 (en) | 1976-02-17 | 1982-06-09 | Process for preparing novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts |
Country Status (16)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3062216D1 (en) * | 1979-09-06 | 1983-04-07 | Beecham Group Plc | Cinnamic acid derivatives, their preparation, and pharmaceutical compositions containing them |
| DE3125870C2 (de) * | 1980-07-09 | 1994-09-15 | William John Louis | 3-Aminopropoxyphenyl Derivate, ihre Herstellung und sie enthaltende Arzneimittel |
| WO2008120655A1 (ja) | 2007-03-30 | 2008-10-09 | Institute Of Medicinal Molecular Design, Inc. | Ｉ型１１βヒドロキシステロイド脱水素酵素阻害活性を有するオキサゾリジノン誘導体 |
-
1976
- 1976-02-17 DE DE19762606140 patent/DE2606140A1/de not_active Withdrawn
-
1977
- 1977-01-20 FI FI770170A patent/FI770170A7/fi not_active Application Discontinuation
- 1977-02-03 AT AT67677A patent/AT355008B/de not_active IP Right Cessation
- 1977-02-15 LU LU76774A patent/LU76774A1/xx unknown
- 1977-02-15 CH CH184777A patent/CH634820A5/de not_active IP Right Cessation
- 1977-02-16 NO NO770509A patent/NO143345C/no unknown
- 1977-02-16 BE BE174995A patent/BE851503A/xx not_active IP Right Cessation
- 1977-02-16 SE SE7701724A patent/SE7701724L/xx not_active Application Discontinuation
- 1977-02-16 ES ES455942A patent/ES455942A1/es not_active Expired
- 1977-02-16 AU AU22334/77A patent/AU512322B2/en not_active Expired
- 1977-02-16 JP JP1600477A patent/JPS52100433A/ja active Pending
- 1977-02-16 NL NL7701613A patent/NL7701613A/xx not_active Application Discontinuation
- 1977-02-16 DK DK66177A patent/DK66177A/da not_active Application Discontinuation
- 1977-02-16 GB GB6521/77A patent/GB1544883A/en not_active Expired
- 1977-02-17 IE IE341/77A patent/IE45186B1/en unknown
- 1977-02-17 FR FR7704568A patent/FR2341557A1/fr active Granted
- 1977-12-02 ES ES464832A patent/ES464832A1/es not_active Expired
- 1977-12-07 ES ES464837A patent/ES464837A1/es not_active Expired
- 1977-12-07 ES ES464834A patent/ES464834A1/es not_active Expired
- 1977-12-07 ES ES464833A patent/ES464833A1/es not_active Expired
- 1977-12-07 ES ES464835A patent/ES464835A1/es not_active Expired
- 1977-12-07 ES ES464836A patent/ES464836A1/es not_active Expired
-
1981
- 1981-08-26 CH CH550381A patent/CH634821A5/de not_active IP Right Cessation
- 1981-08-26 CH CH550481A patent/CH634822A5/de not_active IP Right Cessation
-
1982
- 1982-06-09 CH CH357282A patent/CH635569A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO770509L (no) | 1977-08-18 |
| CH634821A5 (en) | 1983-02-28 |
| LU76774A1 (enrdf_load_stackoverflow) | 1978-04-13 |
| NO143345B (no) | 1980-10-13 |
| ES464836A1 (es) | 1978-08-01 |
| FR2341557A1 (fr) | 1977-09-16 |
| IE45186B1 (en) | 1982-07-14 |
| FR2341557B1 (enrdf_load_stackoverflow) | 1980-08-14 |
| ES455942A1 (es) | 1978-11-01 |
| NL7701613A (nl) | 1977-08-19 |
| AT355008B (de) | 1980-02-11 |
| CH634822A5 (en) | 1983-02-28 |
| GB1544883A (en) | 1979-04-25 |
| AU512322B2 (en) | 1980-10-02 |
| BE851503A (fr) | 1977-08-16 |
| NO143345C (no) | 1981-01-21 |
| ES464837A1 (es) | 1978-08-01 |
| JPS52100433A (en) | 1977-08-23 |
| ES464834A1 (es) | 1978-09-01 |
| ES464835A1 (es) | 1979-09-16 |
| DE2606140A1 (de) | 1977-08-25 |
| SE7701724L (sv) | 1977-08-18 |
| ES464832A1 (es) | 1978-09-01 |
| FI770170A7 (enrdf_load_stackoverflow) | 1977-08-18 |
| ATA67677A (de) | 1979-07-15 |
| AU2233477A (en) | 1978-08-24 |
| DK66177A (da) | 1977-08-18 |
| CH635569A5 (en) | 1983-04-15 |
| ES464833A1 (es) | 1978-09-01 |
| IE45186L (en) | 1977-08-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1111642B (de) | Verfahren zur Herstellung von basisch substituierten Diphenylmethan-Derivaten mit Herz- und Kreislaufwirksamkeit | |
| DE1493955A1 (de) | Verfahren zur Herstellung substituierter Sulfonanilide | |
| DE2334404C2 (de) | Alkylthiophenyl-2-n-octylaminoalkohole und deren Salze, Verfahren zu deren Herstellung und pharmazeutische Zubereitung | |
| DE2461604C2 (enrdf_load_stackoverflow) | ||
| DE2059985A1 (de) | Optisch aktive,basisch substituierte Phenylacetonitrile | |
| CH634820A5 (en) | Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. | |
| DE2225332A1 (de) | 1 eckige Klammer auf 4 Hydroxy 3 (hydroxymethyl) phenyl eckige Klammer zu 1 hydroxy 2 aralkylaminoathane | |
| DE1936206A1 (de) | Diphenylmethoxyaethylaminoderivate und Verfahren zu ihrer Herstellung | |
| CH637108A5 (en) | Process for preparing novel 1-aryloxy-2-hydroxy-3-aminopropanes | |
| EP0000013B1 (de) | 4-Phenyl-8-amino-tetrahydroisochinoline, diese enthaltende pharmazeutische Präparate und Verfahren zur Herstellung dieser Präparate | |
| AT256816B (de) | Verfahren zur Herstellung von neuen substituierten 1-Phenyl-2-aminoalkanolen und deren Säureadditionssalzen | |
| US4333930A (en) | Orthoarylideneaminophenethylamines and pharmaceutical compositions | |
| JPS6145618B2 (enrdf_load_stackoverflow) | ||
| AT213877B (de) | Verfahren zur Herstellung von neuen basisch substituierten Diphenylalkan-Derivaten und deren Säureadditionssalzen bzw. quartären Ammoniumsalzen | |
| DE2324584A1 (de) | Neue amine und verfahren zu ihrer herstellung | |
| US4104402A (en) | 5,6-Dihydroxy aminotetralol compounds | |
| EP0031910B1 (de) | Anilinderivate, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung | |
| DE1620128B2 (de) | N-aminoalkyl-2-phenoxy-2-phenylacetamide, deren saeureadditionssalze, sowie verfahren zu ihrer herstellung | |
| DE2166997C3 (de) | Verfahren zur Herstellung von 4,4-Diphenyl-piperidinen | |
| DE68905259T2 (de) | Derivate von benzocyclohepten, verfahren zu ihrer herstellung und sie enthaltende arzneimittel. | |
| AT366025B (de) | Verfahren zur herstellung neuer 1-(2-phenyl-2-hydroxyaethylamino)-3-phenoxy-propan-2-olen | |
| Sunko et al. | Studies in the Sphingolipids Series. II. Synthesis of Enantiomeric Sphingines | |
| DE953803C (de) | Verfahren zur Herstellung von Alkaminestern von 4-Amino-2-oxybenzoesaeure, die am N-und O-Atom alkyliert sind | |
| DD149664A5 (de) | Verfahren zur herstellung von 1,1'-biphenyl-2-yl-alkylamin-derivaten | |
| DD148720A5 (de) | Verfahren zur herstellung von 4-amino-2-piperidinochinazolin-derivaten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |