JPH0329782B2 - - Google Patents
Info
- Publication number
- JPH0329782B2 JPH0329782B2 JP52045628A JP4562877A JPH0329782B2 JP H0329782 B2 JPH0329782 B2 JP H0329782B2 JP 52045628 A JP52045628 A JP 52045628A JP 4562877 A JP4562877 A JP 4562877A JP H0329782 B2 JPH0329782 B2 JP H0329782B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyphenyl
- aminopropane
- gepefrine
- bitartrate
- effects
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical class OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims description 11
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 9
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 5
- 208000001953 Hypotension Diseases 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 230000036543 hypotension Effects 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- WTDGMHYYGNJEKQ-UHFFFAOYSA-N alpha-Methyl-m-tyramine Chemical compound CC(N)CC1=CC=CC(O)=C1 WTDGMHYYGNJEKQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000008378 aryl ethers Chemical class 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 230000000694 effects Effects 0.000 description 22
- 229960005059 gepefrine Drugs 0.000 description 22
- WTDGMHYYGNJEKQ-ZETCQYMHSA-N gepefrine Chemical compound C[C@H](N)CC1=CC=CC(O)=C1 WTDGMHYYGNJEKQ-ZETCQYMHSA-N 0.000 description 22
- 241001465754 Metazoa Species 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 230000036772 blood pressure Effects 0.000 description 10
- 239000003814 drug Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 230000031700 light absorption Effects 0.000 description 7
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 230000000144 pharmacologic effect Effects 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 241000282693 Cercopithecidae Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000001154 acute effect Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000010253 intravenous injection Methods 0.000 description 4
- 210000003734 kidney Anatomy 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 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 3
- 206010047139 Vasoconstriction Diseases 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000017531 blood circulation Effects 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229960002748 norepinephrine Drugs 0.000 description 3
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- -1 1-(3-hydroxyphenyl)-2-aminopropane -(+)-1-(3-Hydroxyphenyl)-2-aminopropane Chemical compound 0.000 description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 206010003694 Atrophy Diseases 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000013016 Hypoglycemia Diseases 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000150 Sympathomimetic Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000037444 atrophy Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000035487 diastolic blood pressure Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 238000010562 histological examination Methods 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 210000001147 pulmonary artery Anatomy 0.000 description 2
- 208000002815 pulmonary hypertension Diseases 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001975 sympathomimetic effect Effects 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000035488 systolic blood pressure Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 238000005353 urine analysis Methods 0.000 description 2
- 230000025033 vasoconstriction Effects 0.000 description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
- OSBHHTXUNQCORF-UHFFFAOYSA-N 2-aminopropyl acetate Chemical compound CC(N)COC(C)=O OSBHHTXUNQCORF-UHFFFAOYSA-N 0.000 description 1
- SQVIAVUSQAWMKL-UHFFFAOYSA-N 3-[2-(ethylamino)-1-hydroxyethyl]phenol Chemical compound CCNCC(O)C1=CC=CC(O)=C1 SQVIAVUSQAWMKL-UHFFFAOYSA-N 0.000 description 1
- BZFKSWOGZQMOMO-UHFFFAOYSA-N 3-chloropropan-1-amine Chemical compound NCCCCl BZFKSWOGZQMOMO-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 206010054089 Depressive symptom Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000001951 Fetal Death Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028400 Mutagenic effect Diseases 0.000 description 1
- 231100000229 OECD 452 Chronic Toxicity Study Toxicity 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- 206010048010 Withdrawal syndrome Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- PZYQCJTXVVWYSS-SNVBAGLBSA-N [(2R)-2-amino-3-(3-hydroxyphenyl)propyl] acetate Chemical compound OC=1C=C(C=CC=1)C[C@H](COC(C)=O)N PZYQCJTXVVWYSS-SNVBAGLBSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 239000000695 adrenergic alpha-agonist Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000010876 biochemical test Methods 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 229960004695 etilefrine Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 231100000479 fetal death Toxicity 0.000 description 1
- 231100001048 fetal toxicity Toxicity 0.000 description 1
- 231100000311 fetotoxic Toxicity 0.000 description 1
- 230000002291 fetotoxic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 238000011206 morphological examination Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 231100000243 mutagenic effect Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229960001856 norfenefrine Drugs 0.000 description 1
- LRCXRAABFLIVAI-UHFFFAOYSA-N norfenefrine Chemical compound NCC(O)C1=CC=CC(O)=C1 LRCXRAABFLIVAI-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000009596 postnatal growth Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 229940064707 sympathomimetics Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000005526 vasoconstrictor 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
-
- A—HUMAN NECESSITIES
- A63—SPORTS; GAMES; AMUSEMENTS
- A63B—APPARATUS FOR PHYSICAL TRAINING, GYMNASTICS, SWIMMING, CLIMBING, OR FENCING; BALL GAMES; TRAINING EQUIPMENT
- A63B22/00—Exercising apparatus specially adapted for conditioning the cardio-vascular system, for training agility or co-ordination of movements
- A63B22/0025—Particular aspects relating to the orientation of movement paths of the limbs relative to the body; Relative relationship between the movements of the limbs
- A63B2022/0033—Lower limbs performing together the same movement, e.g. on a single support element
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary 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 |
|---|---|---|---|
| AT504676A AT343625B (de) | 1976-07-09 | 1976-07-09 | Verfahren zur herstellung von neuen saureadditionssalzen des d-(+)-1- (m-hydroxyphenyl) -2-aminopropans |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS539727A JPS539727A (en) | 1978-01-28 |
| JPH0329782B2 true JPH0329782B2 (xx) | 1991-04-25 |
Family
ID=3571321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4562877A Granted JPS539727A (en) | 1976-07-09 | 1977-04-20 | Dd****11*33hydroxyphenyl**22am1no propane acid addition salt*its use and process for producing the same |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS539727A (xx) |
| AR (1) | AR216467A1 (xx) |
| AT (1) | AT343625B (xx) |
| BE (1) | BE853332A (xx) |
| CH (1) | CH629732A5 (xx) |
| DE (1) | DE2712860C3 (xx) |
| DK (1) | DK159203C (xx) |
| ES (1) | ES457992A1 (xx) |
| FR (1) | FR2357529A1 (xx) |
| GB (1) | GB1527479A (xx) |
| GR (1) | GR69605B (xx) |
| NL (1) | NL176744C (xx) |
| PT (1) | PT66752B (xx) |
| SE (1) | SE440902B (xx) |
| SU (1) | SU973018A3 (xx) |
| ZA (1) | ZA771767B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3209788C2 (de) * | 1982-03-15 | 1984-10-04 | Rolf 1000 Berlin Sachse | Verfahren zur Herstellung von 1-(3-Hydroxyphenyl)-2-aminopropan |
| DK600285D0 (da) * | 1985-12-20 | 1985-12-20 | Jens Erik Sattrup | Fremgangsmaade til fremstilling af en dybtrykcylinder |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5013784A (xx) * | 1973-06-08 | 1975-02-13 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB396951A (en) * | 1931-09-19 | 1933-08-17 | Ig Farbenindustrie Ag | Manufacture of optically active 1-monohydroxy-phenyl-2-aminopropanols(1) |
-
1976
- 1976-07-09 AT AT504676A patent/AT343625B/de not_active IP Right Cessation
-
1977
- 1977-02-25 GR GR52852A patent/GR69605B/el unknown
- 1977-03-04 SE SE7702469A patent/SE440902B/xx not_active IP Right Cessation
- 1977-03-21 DE DE2712860A patent/DE2712860C3/de not_active Expired
- 1977-03-23 DK DK127277A patent/DK159203C/da not_active IP Right Cessation
- 1977-03-24 ZA ZA00771767A patent/ZA771767B/xx unknown
- 1977-04-07 BE BE176488A patent/BE853332A/xx not_active IP Right Cessation
- 1977-04-07 FR FR7710639A patent/FR2357529A1/fr active Granted
- 1977-04-20 ES ES457992A patent/ES457992A1/es not_active Expired
- 1977-04-20 JP JP4562877A patent/JPS539727A/ja active Granted
- 1977-04-25 CH CH510277A patent/CH629732A5/de not_active IP Right Cessation
- 1977-05-13 AR AR267625A patent/AR216467A1/es active
- 1977-06-01 GB GB23228/77A patent/GB1527479A/en not_active Expired
- 1977-06-14 NL NLAANVRAGE7706510,A patent/NL176744C/xx not_active IP Right Cessation
- 1977-06-30 PT PT66752A patent/PT66752B/pt unknown
- 1977-07-01 SU SU772502045A patent/SU973018A3/ru active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5013784A (xx) * | 1973-06-08 | 1975-02-13 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2712860B2 (de) | 1980-07-10 |
| AR216467A1 (es) | 1979-12-28 |
| DE2712860C3 (de) | 1981-04-02 |
| CH629732A5 (en) | 1982-05-14 |
| JPS539727A (en) | 1978-01-28 |
| SU973018A3 (ru) | 1982-11-07 |
| GB1527479A (en) | 1978-10-04 |
| FR2357529B1 (xx) | 1979-03-02 |
| NL176744C (nl) | 1985-06-03 |
| DK159203C (da) | 1991-02-11 |
| NL7706510A (nl) | 1978-01-11 |
| ZA771767B (en) | 1978-03-29 |
| BE853332A (fr) | 1977-08-01 |
| ES457992A1 (es) | 1978-07-16 |
| DK127277A (da) | 1978-01-10 |
| DE2712860A1 (de) | 1978-01-12 |
| DK159203B (da) | 1990-09-17 |
| ATA504676A (de) | 1977-10-15 |
| SE7702469L (sv) | 1978-01-10 |
| FR2357529A1 (fr) | 1978-02-03 |
| PT66752A (de) | 1977-07-01 |
| GR69605B (xx) | 1982-07-05 |
| SE440902B (sv) | 1985-08-26 |
| PT66752B (de) | 1978-11-27 |
| AT343625B (de) | 1978-06-12 |
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