PL70430B1 - Phenylaminoethanol derivatives[gb1200886a] - Google Patents
Phenylaminoethanol derivatives[gb1200886a] Download PDFInfo
- Publication number
- PL70430B1 PL70430B1 PL1967122667A PL12266767A PL70430B1 PL 70430 B1 PL70430 B1 PL 70430B1 PL 1967122667 A PL1967122667 A PL 1967122667A PL 12266767 A PL12266767 A PL 12266767A PL 70430 B1 PL70430 B1 PL 70430B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- compound
- group
- benzyl
- defined above
- Prior art date
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- ULZRKSDAMUWQEZ-UHFFFAOYSA-N 1-anilinoethanol Chemical class CC(O)NC1=CC=CC=C1 ULZRKSDAMUWQEZ-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000002360 preparation method Methods 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 150000002576 ketones Chemical class 0.000 claims abstract description 3
- 150000001299 aldehydes Chemical class 0.000 claims abstract 2
- -1 alkyl radical Chemical class 0.000 claims description 69
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 230000002829 reductive effect Effects 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 239000012279 sodium borohydride Substances 0.000 claims description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 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 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- 239000007818 Grignard reagent Substances 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000004795 grignard reagents Chemical class 0.000 claims description 2
- 150000003944 halohydrins Chemical class 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 238000005932 reductive alkylation reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 229910052799 carbon Inorganic materials 0.000 abstract description 6
- 230000009471 action Effects 0.000 abstract description 3
- 230000000903 blocking effect Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
- 108060003345 Adrenergic Receptor Proteins 0.000 abstract 1
- 102000017910 Adrenergic receptor Human genes 0.000 abstract 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 abstract 1
- 150000002902 organometallic compounds Chemical class 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 64
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
- 239000000203 mixture Substances 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 229910003445 palladium oxide Inorganic materials 0.000 description 11
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- 229960000581 salicylamide Drugs 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 229960001317 isoprenaline Drugs 0.000 description 7
- 229960004889 salicylic acid Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000036772 blood pressure Effects 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 230000004936 stimulating effect Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 3
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 3
- 229940124630 bronchodilator Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229960003712 propranolol Drugs 0.000 description 3
- 238000011946 reduction process Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000000021 stimulant Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000007883 bronchodilation Effects 0.000 description 2
- 239000000168 bronchodilator agent Substances 0.000 description 2
- 230000009084 cardiovascular function Effects 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 2
- 239000005337 ground glass Substances 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 2
- AWXOSGITYMTEBI-UHFFFAOYSA-N methyl 5-[2-[benzyl(propan-2-yl)amino]acetyl]-2-hydroxybenzoate;hydrochloride Chemical compound Cl.C1=C(O)C(C(=O)OC)=CC(C(=O)CN(CC=2C=CC=CC=2)C(C)C)=C1 AWXOSGITYMTEBI-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 239000013081 microcrystal Substances 0.000 description 2
- FWVGYDHKFPHNHP-UHFFFAOYSA-N n,2-dihydroxy-5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzamide Chemical compound CC(C)NCC(O)C1=CC=C(O)C(C(=O)NO)=C1 FWVGYDHKFPHNHP-UHFFFAOYSA-N 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- JPEYJQDKTDVJSZ-UHFFFAOYSA-N (2,6-dimethylphenyl)methanol Chemical group CC1=CC=CC(C)=C1CO JPEYJQDKTDVJSZ-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical group CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 1
- BZIMCBIAROVCGC-UHFFFAOYSA-N 2-hydroxybenzamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=CC=C1O BZIMCBIAROVCGC-UHFFFAOYSA-N 0.000 description 1
- ZXACBHMKACDPEG-UHFFFAOYSA-N 2-hydroxybenzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1O ZXACBHMKACDPEG-UHFFFAOYSA-N 0.000 description 1
- YPTHXEDEWZDCLB-UHFFFAOYSA-N 3-(dimethylamino)-2-ethoxybenzoic acid Chemical compound CN(C)C=1C(=C(C(=O)O)C=CC=1)OCC YPTHXEDEWZDCLB-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
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- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
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- 206010003119 arrhythmia Diseases 0.000 description 1
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- 235000010233 benzoic acid Nutrition 0.000 description 1
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- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
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- 230000027119 gastric acid secretion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- HQLZFBUAULNEGP-UHFFFAOYSA-N hexan-3-amine Chemical compound CCCC(N)CC HQLZFBUAULNEGP-UHFFFAOYSA-N 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
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- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- MGVCJPIRFFWQIE-UHFFFAOYSA-N methyl 2-hydroxybenzoate hydrochloride Chemical compound C(C=1C(O)=CC=CC1)(=O)OC.Cl MGVCJPIRFFWQIE-UHFFFAOYSA-N 0.000 description 1
- FVWZMDORPRMMDU-UHFFFAOYSA-N methyl 4-(2-bromoacetyl)-2-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(C(=O)CBr)C=C1O FVWZMDORPRMMDU-UHFFFAOYSA-N 0.000 description 1
- AKWQRVIQUREMOK-UHFFFAOYSA-N methyl 5-(2-bromoacetyl)-2-phenylmethoxybenzoate Chemical compound COC(=O)C1=CC(C(=O)CBr)=CC=C1OCC1=CC=CC=C1 AKWQRVIQUREMOK-UHFFFAOYSA-N 0.000 description 1
- HWLMCRZJMPDSRW-UHFFFAOYSA-N methyl 5-[2-(tert-butylamino)-1-hydroxyethyl]-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(C(O)CNC(C)(C)C)=CC=C1O HWLMCRZJMPDSRW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- GLMUAFMGXXHGLU-VQAITOIOSA-N minocycline hydrochloride Chemical group [H+].[Cl-].C([C@H]1C2)C3=C(N(C)C)C=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O GLMUAFMGXXHGLU-VQAITOIOSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
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- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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- 229940001158 ximino Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB18383/67A GB1200886A (en) | 1966-09-23 | 1966-09-23 | Phenylaminoethanol derivatives |
| GB1838367 | 1967-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL70430B1 true PL70430B1 (en) | 1974-02-28 |
Family
ID=26253347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1967122667A PL70430B1 (en) | 1966-09-23 | 1967-09-20 | Phenylaminoethanol derivatives[gb1200886a] |
Country Status (15)
Families Citing this family (149)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES373606A1 (es) * | 1968-11-18 | 1972-06-01 | Pfizer | Un procedimiento para la preparacion de nuevos derivados depropanolamina. |
| US4101579A (en) * | 1969-02-06 | 1978-07-18 | Allen & Hanburys Limited | Phenethanolamine ethers |
| GB1266058A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-07-08 | 1972-03-08 | ||
| US4012444A (en) * | 1969-07-08 | 1977-03-15 | Allen & Hanburys Limited | 5-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl] salicylamide and physiologically acceptable acid addition salts thereof |
| GB1298494A (en) * | 1970-06-17 | 1972-12-06 | Allen & Hanburys Ltd | Phenylethanolamine derivatives |
| AT310146B (de) * | 1971-04-26 | 1973-09-25 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen N,N'-Bis-(β-hydroxyaryläthyl)-diaminoalkanen und deren Säureadditionssalzen |
| BE794414A (fr) * | 1972-01-25 | 1973-07-23 | Sandoz Sa | Nouveaux amino-alcools, leur preparation et leur application comme medicament |
| US4018825A (en) * | 1972-07-27 | 1977-04-19 | Warner-Lambert Company | 5-Hydroxy-α-(substituted aminomethyl)-m-xylene-α,α'-diols |
| US4024255A (en) * | 1973-04-05 | 1977-05-17 | Allen & Hanburys Limited | Tetrazole containing naphthyridine-3-carboxamides |
| US4000192A (en) * | 1973-05-07 | 1976-12-28 | Allen & Hanburys Limited | Pharmacologically active compounds |
| GB1468673A (en) * | 1973-05-07 | 1977-03-30 | Allen & Hanburys Ltd | Substituted benzamides |
| US3883560A (en) * | 1973-07-05 | 1975-05-13 | Colgate Palmolive Co | Salicylamidophenethanolamines |
| US4046913A (en) * | 1973-08-18 | 1977-09-06 | Boehringer Ingelheim Gmbh | 1-(M-alkanoyloxy-phenyl)-1-hydroxy-2-(N-lower alkyl-amino)-ethanes and salts thereof |
| US4022776A (en) * | 1974-01-31 | 1977-05-10 | Otsuka Pharmaceutical Company Limited | 5-[1-Hydroxy-2-(substituted-amino)]ethyl-8-hydroxycarbostyril derivatives |
| US4093628A (en) * | 1974-04-18 | 1978-06-06 | American Home Products Corporation | Thiophene ethanolamines |
| US4012528A (en) * | 1974-06-03 | 1977-03-15 | Smithkline Corporation | α-AMINOALKYL-3-(1,2-DIHYDROXYETHYL)-4-HYDROXY-BENZYL ALCOHOLS HAVING β-ADRENERGIC STIMULANT ACTIVITY |
| US4173583A (en) * | 1975-04-17 | 1979-11-06 | Schering Corporation | Diastereoisomers of 5-(1-hydroxy-2-(1-methyl-3-phenylpropylamino)ethyl)salicylamide |
| GB1529972A (en) * | 1975-07-29 | 1978-10-25 | Allen & Hanburys Ltd | Basic alcohols |
| US4160036A (en) * | 1975-07-29 | 1979-07-03 | Allen & Hanburys Limited | 4-Hydroxy-1,3-benzenedimethanol derivatives |
| US4154761A (en) * | 1976-02-09 | 1979-05-15 | Allen & Hanburys Limited | Pharmacologically active compounds |
| JPS52113934A (en) * | 1976-03-19 | 1977-09-24 | Eisai Co Ltd | Phenethylamine derivatives and bronchodilator containing the same |
| US4055658A (en) * | 1976-05-17 | 1977-10-25 | Mead Johnson & Company | Cyanomethylphenethanolamines |
| US4127674A (en) * | 1977-03-21 | 1978-11-28 | Allergan Pharmaceuticals, Inc. | Method of treatment for glaucoma |
| US4163053A (en) * | 1977-12-27 | 1979-07-31 | Schering Corporation | Anti-hypertensive 5-[2-(substituted anilinoalkylamino)-1-hydroxyalkyl]salicylamides |
| DK160936C (da) * | 1978-07-03 | 1991-10-21 | Lilly Co Eli | Analogifremgangsmaade til fremstilling af optisk aktive phenethanolaminer |
| DE2833140A1 (de) * | 1978-07-28 | 1980-02-07 | Boehringer Sohn Ingelheim | Neue n-substituierte heterocyclen |
| DE2935062A1 (de) * | 1978-09-06 | 1980-03-20 | Degussa | Substituierte aminoalkylguanidine, deren herstellung und arzneimittel |
| US4950783A (en) * | 1978-09-20 | 1990-08-21 | Schering Corporation | Treatment of hypertension |
| US4590210A (en) * | 1979-03-09 | 1986-05-20 | Langham Maurice E | Compositions for treatment of ocular hypertension |
| US4275074A (en) * | 1979-03-09 | 1981-06-23 | Graham J. Dobbie | Catecholamine treatment of ocular hypertension |
| IT1148741B (it) * | 1980-11-28 | 1986-12-03 | Zambeletti Spa L | Procedimento per la preparazione dell'1-(3,5-dimetossi-4-idrossifenil)-2-(n-metilammino)etanolo cloridrato |
| US4348398A (en) * | 1980-12-23 | 1982-09-07 | Merck Sharp & Dohme (I.A.) Corp. | Quinolinyl ethanolamines |
| US4358455A (en) * | 1980-12-23 | 1982-11-09 | Merck & Co., Inc. | Aralkylamindethanol heterocyclic compounds |
| US4486446A (en) * | 1980-12-23 | 1984-12-04 | Merck & Co., Inc. | Aralkylaminoethanol heterocyclic compounds |
| US4379166A (en) * | 1981-08-03 | 1983-04-05 | Schering Corporation | Arylmethoxy-, arylmethylthio-, heteroarylmethoxy-, and heteroarylmethylthio-alkylaminoalcohols |
| CA1219865A (en) * | 1982-05-14 | 1987-03-31 | Leo Alig | Aziridine phenethanolamine derivatives |
| CH656308A5 (fr) * | 1982-05-27 | 1986-06-30 | Glaxo Group Ltd | Compositions pharmaceutiques contenant du salbutamol. |
| US4594359B1 (en) * | 1982-05-27 | 1994-07-26 | Glaxo Group Ltd | Pharmaceutical compositions |
| GB2120942B (en) * | 1982-05-27 | 1985-10-30 | Glaxo Group Ltd | Salbutamol compositions |
| CA1258454A (en) * | 1982-08-10 | 1989-08-15 | Leo Alig | Phenethanolamines |
| EP0103830A3 (de) * | 1982-09-22 | 1985-07-31 | Bayer Ag | Wachstumsfördernde Phenylethylamin-Derivate |
| ZW6584A1 (en) * | 1983-04-18 | 1985-04-17 | Glaxo Group Ltd | Phenethanolamine derivatives |
| US4499108A (en) * | 1983-06-08 | 1985-02-12 | Schering Corporation | Stable pleasant-tasting albuterol sulfate pharmaceutical formulations |
| US4751071A (en) * | 1983-12-01 | 1988-06-14 | Alza Corporation | Composition comprising salbutamol |
| US4851229A (en) * | 1983-12-01 | 1989-07-25 | Alza Corporation | Composition comprising a therapeutic agent and a modulating agent |
| US4777049A (en) * | 1983-12-01 | 1988-10-11 | Alza Corporation | Constant release system with pulsed release |
| US4853381A (en) * | 1984-04-17 | 1989-08-01 | Glaxo Group Limited | Ethanolamine compounds |
| SE8501895L (sv) * | 1984-04-17 | 1985-10-18 | Glaxo Group Ltd | Fenetanolaminforeningar |
| US5250546A (en) * | 1984-09-28 | 1993-10-05 | Nippon Chemiphar Co., Ltd. | Amino-alcohol derivatives and processes for their preparation |
| JPS6183147A (ja) * | 1984-09-28 | 1986-04-26 | Nippon Chemiphar Co Ltd | 新規なアミノアルコール誘導体およびその製造法並びにそれを有効成分とするグルタミン酸遮断剤 |
| US4952729A (en) * | 1986-09-05 | 1990-08-28 | Schering-Plough Corp. | Intermediates in the preparation of alpha1(((1,1-dimethylethyl) amino) methyl)-4-hydroxy-1,3-benzenedimethanol |
| US5011993A (en) * | 1986-09-05 | 1991-04-30 | Schering Corporation | Method for the preparation of α1 [[(1,1-dimethylethyl)amino]methyl]-4-hydroxy-1,3-benzenedimethanol |
| EP0259159A3 (en) * | 1986-09-05 | 1989-08-09 | Schering Corporation | Method for the preparation of alpha1- [[(1,1-Dimethylethyl) amino] methyl]-4-hydroxy-1,3-benzenedimethanol, and intermediates used in its preparation |
| US5453418A (en) * | 1988-03-07 | 1995-09-26 | Eli Lilly And Company | Ractopamine and growth hormone combinations |
| US5030640A (en) * | 1989-01-05 | 1991-07-09 | Merck & Co., Inc. | Novel β-adrenergic agonists and pharmaceutical compositions thereof |
| US5166437A (en) * | 1989-03-03 | 1992-11-24 | Orion-Yhtyma Oy | Process for the preparation of fluoxetine |
| GB8909273D0 (en) * | 1989-04-24 | 1989-06-07 | Glaxo Group Ltd | Chemical compounds |
| MY105368A (en) | 1990-03-02 | 1994-09-30 | Glaxo Group Ltd | Inhalation device. |
| US6536427B2 (en) | 1990-03-02 | 2003-03-25 | Glaxo Group Limited | Inhalation device |
| HU213221B (en) | 1990-03-02 | 1997-03-28 | Glaxo Group Ltd | Inhalation device and medicine packet for device |
| US5118683A (en) * | 1990-06-13 | 1992-06-02 | Schering Corporation | Esters of 4-hydroxy-1,3-benzenedimethanol and compositions and methods employing such compounds |
| WO1991019693A1 (en) * | 1990-06-13 | 1991-12-26 | Schering Corporation | Esters and cyclic diesters of 4-hydroxy-1,3-benzenedimethanol and compositions and methods employing such compounds |
| US5011845A (en) * | 1990-06-13 | 1991-04-30 | Schering Corporation | Cyclic diesters of 4-hydroxy-1,3-benzenedimethanol and compositions and methods employing such compounds |
| JPH07113006B2 (ja) * | 1990-09-11 | 1995-12-06 | シェリング・コーポレーション | アルブテロール、およびその中間体であるアセタール、ヘミアセタールおよびアリールグリオキサール水化物の製造方法 |
| US5182097A (en) * | 1991-02-14 | 1993-01-26 | Virginia Commonwealth University | Formulations for delivery of drugs by metered dose inhalers with reduced or no chlorofluorocarbon content |
| ZA924164B (en) * | 1991-06-10 | 1993-02-24 | Schering Corp | Non-chlorofluorocarbon aerosol formulations |
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| US7101534B1 (en) | 1991-12-18 | 2006-09-05 | 3M Innovative Properties Company | Suspension aerosol formulations |
| US7105152B1 (en) | 1991-12-18 | 2006-09-12 | 3M Innovative Properties Company | Suspension aerosol formulations |
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| US5475138A (en) * | 1994-07-07 | 1995-12-12 | Pharm-Eco Laboratories Incorporated | Method preparing amino acid-derived diaminopropanols |
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| BR9604978A (pt) | 1995-04-14 | 1998-06-09 | Glaxo Wellcome Inc | Inalador com dose medida |
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| US5770615A (en) * | 1996-04-04 | 1998-06-23 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| EP0801060A1 (en) * | 1996-04-09 | 1997-10-15 | Pfizer Inc. | Heterocyclic Beta-3 Adrenergenic Agonists |
| US20030103906A1 (en) * | 1997-10-14 | 2003-06-05 | Smithkline Beecham Corporation | Metered dose inhaler having internal surfaces coated with fluorocarbon polymer |
| ZA994264B (en) * | 1998-07-01 | 2000-01-25 | Warner Lambert Co | Stereoisomers with high affinity for adrenergic receptors. |
| US7232837B2 (en) * | 1999-06-29 | 2007-06-19 | Mcneil-Ppc, Inc. | Stereoisomers with high affinity for adrenergic receptors |
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-
1966
- 1966-09-23 GB GB18383/67A patent/GB1200886A/en not_active Expired
-
1967
- 1967-09-18 IL IL28643A patent/IL28643A/en unknown
- 1967-09-19 BE BE704037D patent/BE704037A/xx not_active IP Right Cessation
- 1967-09-20 US US669263A patent/US3644353A/en not_active Expired - Lifetime
- 1967-09-20 PL PL1967122667A patent/PL70430B1/pl unknown
- 1967-09-22 NO NO169835A patent/NO126014B/no unknown
- 1967-09-22 SE SE13078/67A patent/SE354061B/xx unknown
- 1967-09-22 NL NL6713016.A patent/NL160805C/xx not_active IP Right Cessation
- 1967-09-22 AT AT864367A patent/AT280996B/de not_active IP Right Cessation
- 1967-09-22 DE DE1643224A patent/DE1643224C3/de not_active Expired
- 1967-09-22 DK DK473167AA patent/DK133618B/da not_active IP Right Cessation
- 1967-09-22 CS CS6767*BA patent/CS167874B2/cs unknown
- 1967-09-25 CH CH1333967A patent/CH492676A/de not_active IP Right Cessation
- 1967-09-25 FR FR122101A patent/FR8010M/fr not_active Expired
- 1967-09-25 FR FR1557677D patent/FR1557677A/fr not_active Expired
-
1968
- 1968-04-15 US US721214A patent/US3642896A/en not_active Expired - Lifetime
-
1971
- 1971-06-02 US US149356A patent/US3705233A/en not_active Expired - Lifetime
-
1973
- 1973-11-26 CY CY71373A patent/CY713A/xx unknown
-
1978
- 1978-10-02 NL NL7809942A patent/NL7809942A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US3642896A (en) | 1972-02-15 |
| CH492676A (de) | 1970-06-30 |
| DE1643224B2 (de) | 1978-11-23 |
| SE354061B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-02-26 |
| US3705233A (en) | 1972-12-05 |
| CY713A (en) | 1973-11-26 |
| FR1557677A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-02-21 |
| DK133618C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-11-08 |
| NO126014B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-12-11 |
| AT280996B (de) | 1970-05-11 |
| GB1200886A (en) | 1970-08-05 |
| BE704037A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-02-01 |
| DK133618B (da) | 1976-06-21 |
| FR8010M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-07-27 |
| IL28643A (en) | 1971-12-29 |
| US3644353A (en) | 1972-02-22 |
| NL160805B (nl) | 1979-07-16 |
| DE1643224A1 (de) | 1972-03-02 |
| NL7809942A (nl) | 1979-01-31 |
| CS167874B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-05-28 |
| NL6713016A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-03-25 |
| DE1643224C3 (de) | 1979-08-09 |
| NL160805C (nl) | 1979-12-17 |
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