FI65233C - Foerfarande foer framstaellning av terapeutiskt anvaendbar 2-hydroxi-5-(1-hydroxi-2-((1,1-dimetyl-2-fenyletyl)amino)etyl)bensenacetonitril - Google Patents

Foerfarande foer framstaellning av terapeutiskt anvaendbar 2-hydroxi-5-(1-hydroxi-2-((1,1-dimetyl-2-fenyletyl)amino)etyl)bensenacetonitril Download PDF

Info

Publication number: FI65233C
Authority: FI; Finland
Prior art keywords: hydroxy; dimethyl; phenylethyl; ethyl; amino
Prior art date: 1976-05-17

Application number

FI771512A

Other languages

English (en)

Finnish (fi)

Other versions

FI771512A7 (fr

FI65233B (fi

Inventor

William E Kreighbaum

William L Matier

Herbert R Roth

Original Assignee

Bristol Myers Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-05-17

Filing date

1977-05-12

Publication date

1984-04-10

1977-05-12 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1977-11-18 Publication of FI771512A7 publication Critical patent/FI771512A7/fi

1983-12-30 Application granted granted Critical

1983-12-30 Publication of FI65233B publication Critical patent/FI65233B/fi

1984-04-10 Publication of FI65233C publication Critical patent/FI65233C/fi

Links

238000000034 method Methods 0.000 title claims description 5
-1 1-HYDROXY-2 - ((1,1-DIMETHYL-2-PHENYLETHYL) AMINO) ETHYL Chemical class 0.000 title description 10
230000001225 therapeutic effect Effects 0.000 title 2
239000002253 acid Substances 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 9
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 5
239000012279 sodium borohydride Substances 0.000 claims description 4
229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
FALXAJFIYOLQQL-UHFFFAOYSA-N 2-[2-hydroxy-5-[2-[(2-methyl-1-phenylpropan-2-yl)amino]acetyl]phenyl]acetonitrile Chemical compound C=1C=C(O)C(CC#N)=CC=1C(=O)CNC(C)(C)CC1=CC=CC=C1 FALXAJFIYOLQQL-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
OXXDPHIQPAQINB-UHFFFAOYSA-N 2-phenylacetonitrile;hydrochloride Chemical compound Cl.N#CCC1=CC=CC=C1 OXXDPHIQPAQINB-UHFFFAOYSA-N 0.000 description 7
XPHJAEIFIFDYTC-UHFFFAOYSA-N 2-(5-acetyl-2-hydroxyphenyl)acetonitrile Chemical compound CC(=O)C1=CC=C(O)C(CC#N)=C1 XPHJAEIFIFDYTC-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
206010006482 Bronchospasm Diseases 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
241000700199 Cavia porcellus Species 0.000 description 5
241000700159 Rattus Species 0.000 description 5
230000007885 bronchoconstriction Effects 0.000 description 5
229940124630 bronchodilator Drugs 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
241000282472 Canis lupus familiaris Species 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000000464 adrenergic agent Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
230000002269 spontaneous effect Effects 0.000 description 4
238000001665 trituration Methods 0.000 description 4
QLCADKOEWITLKJ-UHFFFAOYSA-N 2-[2-hydroxy-5-[2-[(2-methyl-1-phenylpropan-2-yl)amino]acetyl]phenyl]acetonitrile;hydrochloride Chemical compound Cl.C=1C=C(O)C(CC#N)=CC=1C(=O)CNC(C)(C)CC1=CC=CC=C1 QLCADKOEWITLKJ-UHFFFAOYSA-N 0.000 description 3
YLJJRJMEVZNKTF-UHFFFAOYSA-N 2-[5-(2-bromoacetyl)-2-hydroxyphenyl]acetonitrile Chemical compound OC1=CC=C(C(=O)CBr)C=C1CC#N YLJJRJMEVZNKTF-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000037396 body weight Effects 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
230000004936 stimulating effect Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
LAMHAMBOLINJML-UHFFFAOYSA-N 1-[3-(chloromethyl)-4-hydroxyphenyl]ethanone Chemical compound CC(=O)C1=CC=C(O)C(CCl)=C1 LAMHAMBOLINJML-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
230000002411 adverse Effects 0.000 description 2
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
239000012458 free base Substances 0.000 description 2
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 2
229960002329 methacholine Drugs 0.000 description 2
210000004165 myocardium Anatomy 0.000 description 2
ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 2
229950006768 phenylethanolamine Drugs 0.000 description 2
210000003019 respiratory muscle Anatomy 0.000 description 2
229940076279 serotonin Drugs 0.000 description 2
239000000243 solution Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
230000001960 triggered effect Effects 0.000 description 2
PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
LLLAUEJCYCBLPM-UHFFFAOYSA-N 2-(2-ethylphenyl)acetonitrile Chemical compound CCC1=CC=CC=C1CC#N LLLAUEJCYCBLPM-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
208000009079 Bronchial Spasm Diseases 0.000 description 1
208000014181 Bronchial disease Diseases 0.000 description 1
DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
VUJPXRKBVKYWNU-UHFFFAOYSA-N N-[[5-[2-(tert-butylamino)-1-hydroxyethyl]-2-hydroxyphenyl]methyl]methanesulfonamide Chemical compound C(C)(C)(C)NCC(O)C1=CC=C(C(CNS(=O)(=O)C)=C1)O VUJPXRKBVKYWNU-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
AUALQMFGWLZREY-UHFFFAOYSA-N acetonitrile;methanol Chemical compound OC.CC#N AUALQMFGWLZREY-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
210000005091 airway smooth muscle Anatomy 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
230000001746 atrial effect Effects 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
HXJFQNUWPUICNY-UHFFFAOYSA-N disiamylborane Chemical compound CC(C)C(C)BC(C)C(C)C HXJFQNUWPUICNY-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000439 effect on bronchoconstriction Effects 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
229940039009 isoproterenol Drugs 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000050 smooth muscle relaxant Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000001052 transient effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—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
- A61P9/08—Vasodilators for multiple indications

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Ophthalmology & Optometry (AREA)
Pulmonology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)

FI771512A 1976-05-17 1977-05-12 Foerfarande foer framstaellning av terapeutiskt anvaendbar 2-hydroxi-5-(1-hydroxi-2-((1,1-dimetyl-2-fenyletyl)amino)etyl)bensenacetonitril FI65233C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US68743576		1976-05-17
US05/687,435 US4055658A (en)	1976-05-17	1976-05-17	Cyanomethylphenethanolamines

Publications (3)

Publication Number	Publication Date
FI771512A7 FI771512A7 (fr)	1977-11-18
FI65233B FI65233B (fi)	1983-12-30
FI65233C true FI65233C (fi)	1984-04-10

Family

ID=24760437

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI771512A FI65233C (fi)	1976-05-17	1977-05-12	Foerfarande foer framstaellning av terapeutiskt anvaendbar 2-hydroxi-5-(1-hydroxi-2-((1,1-dimetyl-2-fenyletyl)amino)etyl)bensenacetonitril

Country Status (18)

Country	Link
US (2)	US4055658A (fr)
JP (1)	JPS52139041A (fr)
AU (1)	AU511141B2 (fr)
BE (1)	BE854516A (fr)
CA (1)	CA1095525A (fr)
CH (1)	CH632488A5 (fr)
DE (1)	DE2722398A1 (fr)
DK (1)	DK212377A (fr)
FI (1)	FI65233C (fr)
FR (1)	FR2351949A1 (fr)
GB (1)	GB1524658A (fr)
GR (1)	GR73050B (fr)
IE (1)	IE44839B1 (fr)
LU (1)	LU77313A1 (fr)
NL (1)	NL7705446A (fr)
SE (1)	SE425907B (fr)
YU (1)	YU121877A (fr)
ZA (1)	ZA772843B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3100165B2 (ja) *	1994-11-29	2000-10-16	大日本製薬株式会社	インドール誘導体

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1200886A (en) *	1966-09-23	1970-08-05	Allen & Hanburys Ltd	Phenylaminoethanol derivatives
CH475981A (de) *	1966-12-13	1969-07-31	Sandoz Ag	Verfahren zur Herstellung neuer Indol-Derivate
US3701808A (en) *	1967-12-21	1972-10-31	Allen & Hanburys Ltd	Phenylethanolamines
US3859305A (en) *	1970-03-10	1975-01-07	Degussa	Indole aminoketones
DE2048838A1 (de) *	1970-10-05	1972-04-06	C H Boehnnger Sohn, 6507 Ingel heim	Neue 1 Phenoxy 2 hydroxy 3 hydroxyal kylaminopropane und Verfahren zu ihrer Her stellung
US3718744A (en) *	1971-12-03	1973-02-27	Smith Kline French Lab	Pharmaceutical compositions comprising an alpha-aminoalkyl-4-hydroxy-3-carboalkoxyaminobenzyl alcohol
US3801631A (en) *	1972-02-16	1974-04-02	Mead Johnson & Co	2'-hydroxy-5'-(1-hydroxy-2-(2-methyl-1-phenyl-2-propylamino)ethyl)meth-anesulfonanilide and its salts

1976
- 1976-05-17 US US05/687,435 patent/US4055658A/en not_active Expired - Lifetime
1977
- 1977-04-22 CA CA276,774A patent/CA1095525A/fr not_active Expired
- 1977-05-06 AU AU24948/77A patent/AU511141B2/en not_active Expired
- 1977-05-11 GR GR53439A patent/GR73050B/el unknown
- 1977-05-11 BE BE177487A patent/BE854516A/fr not_active IP Right Cessation
- 1977-05-11 LU LU77313A patent/LU77313A1/xx unknown
- 1977-05-12 ZA ZA00772843A patent/ZA772843B/xx unknown
- 1977-05-12 FI FI771512A patent/FI65233C/fi not_active IP Right Cessation
- 1977-05-13 DK DK212377A patent/DK212377A/da not_active Application Discontinuation
- 1977-05-13 JP JP5449677A patent/JPS52139041A/ja active Pending
- 1977-05-13 GB GB20325/77A patent/GB1524658A/en not_active Expired
- 1977-05-16 YU YU01218/77A patent/YU121877A/xx unknown
- 1977-05-16 IE IE995/77A patent/IE44839B1/en unknown
- 1977-05-16 CH CH609077A patent/CH632488A5/de not_active IP Right Cessation
- 1977-05-16 SE SE7705750A patent/SE425907B/xx unknown
- 1977-05-16 FR FR7714988A patent/FR2351949A1/fr active Granted
- 1977-05-17 DE DE19772722398 patent/DE2722398A1/de not_active Ceased
- 1977-05-17 NL NL7705446A patent/NL7705446A/xx not_active Application Discontinuation
- 1977-09-22 US US05/835,764 patent/US4148908A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPS52139041A (en)	1977-11-19
DE2722398A1 (de)	1977-12-01
FR2351949A1 (fr)	1977-12-16
IE44839B1 (en)	1982-04-07
AU511141B2 (en)	1980-07-31
SE425907B (sv)	1982-11-22
BE854516A (fr)	1977-11-14
FI771512A7 (fr)	1977-11-18
YU121877A (en)	1983-02-28
US4148908A (en)	1979-04-10
US4055658A (en)	1977-10-25
SE7705750L (sv)	1977-11-18
AU2494877A (en)	1978-11-09
GB1524658A (en)	1978-09-13
FI65233B (fi)	1983-12-30
GR73050B (fr)	1984-01-26
ZA772843B (en)	1978-04-26
FR2351949B1 (fr)	1980-06-20
CH632488A5 (de)	1982-10-15
CA1095525A (fr)	1981-02-10
IE44839L (en)	1977-11-17
NL7705446A (nl)	1977-11-21
LU77313A1 (fr)	1977-12-13
DK212377A (da)	1977-11-18

Legal Events

Date	Code	Title	Description
2004-08-31	MM	Patent lapsed	Owner name: BRISTOL-MYERS CO

Publication	Publication Date	Title
SU1632370A3 (ru)	1991-02-28	Способ получени производных феноксиуксусной кислоты или их фармакологически приемлемых солей в форме рацемата или оптически-активного изомера
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BRPI0719187A2 (pt)	2014-09-09	Composto heterocíclicos úteis como agentes anábolicos para animais de criação
US2493710A (en)	1950-01-03	Carbamic acid esters
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JPH0285241A (ja)	1990-03-26	気管支拡張活性を有する化合物
PT87503B (pt)	1992-09-30	Processo para a preparacao de novos derivados de catecolamina
RU2177476C2 (ru)	2001-12-27	Биологически активные этанамины бензотиазолона
FI65233B (fi)	1983-12-30	Foerfarande foer framstaellning av terapeutiskt anvaendbar 2-hydroxi-5-(1-hydroxi-2-((1,1-dimetyl-2-fenyletyl)amino)-etyl)bensenacetonitril
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PT93515B (pt)	1996-08-30	Processo para a preparacao de novas benzotiopiranilaminas
CA1218076A (fr)	1987-02-17	( )s-enantiomere de secoverine a action spasmolytique
US5310941A (en)	1994-05-10	Aminoethylthiophene derivatives
US3961072A (en)	1976-06-01	Phenoxypropanolamine therapeutic agents
NO172115B (no)	1993-03-01	Analogifremgangsmaate for fremstilling av terapeutisk aktive bronkospasmolytiske forbindelser
JPH0326195B2 (fr)	1991-04-10
US3781443A (en)	1973-12-25	Phenethanolamine n-methyl transferase inhibiting benzylamines
FI85140B (fi)	1991-11-29	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara n-(1h-indol-4-yl)-bensamidderivat.
AU599934B2 (en)	1990-08-02	4-alkylamino-alkyl-1,2-benzenediols