CH621540A5 - - Google Patents
Download PDFInfo
- Publication number
- CH621540A5 CH621540A5 CH58676A CH58676A CH621540A5 CH 621540 A5 CH621540 A5 CH 621540A5 CH 58676 A CH58676 A CH 58676A CH 58676 A CH58676 A CH 58676A CH 621540 A5 CH621540 A5 CH 621540A5
- Authority
- CH
- Switzerland
- Prior art keywords
- process according
- compound
- hydrogen
- compounds
- lower alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 93
- 238000000034 method Methods 0.000 claims description 35
- 230000000694 effects Effects 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 22
- 210000003169 central nervous system Anatomy 0.000 claims description 16
- -1 4-ethyl-piperazinyl Chemical group 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000008065 acid anhydrides Chemical class 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000000994 depressogenic effect Effects 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 241000699670 Mus sp. Species 0.000 description 25
- 230000001624 sedative effect Effects 0.000 description 18
- 241001465754 Metazoa Species 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 230000002269 spontaneous effect Effects 0.000 description 13
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 12
- 230000004899 motility Effects 0.000 description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- 230000001143 conditioned effect Effects 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 241000699666 Mus <mouse, genus> Species 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 230000000147 hypnotic effect Effects 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 239000000932 sedative agent Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 5
- 239000012433 hydrogen halide Substances 0.000 description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000002936 tranquilizing effect Effects 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- 208000019901 Anxiety disease Diseases 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 230000000881 depressing effect Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000007958 sleep Effects 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000003444 anaesthetic effect Effects 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 230000003533 narcotic effect Effects 0.000 description 3
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 3
- 229960001412 pentobarbital Drugs 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003204 tranquilizing agent Substances 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 229940125717 barbiturate Drugs 0.000 description 2
- 229960001076 chlorpromazine Drugs 0.000 description 2
- 230000003001 depressive effect Effects 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BRGXUPHMKUCNIZ-UHFFFAOYSA-N n-morpholin-4-yl-5-oxo-5-phenylpentanamide Chemical compound C1COCCN1NC(=O)CCCC(=O)C1=CC=CC=C1 BRGXUPHMKUCNIZ-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YLWLRFLOZYMRPJ-UHFFFAOYSA-N 2-(3,4,5-trimethoxybenzoyl)butanoic acid Chemical compound CCC(C(O)=O)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 YLWLRFLOZYMRPJ-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 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
- KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical compound OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 208000031361 Hiccup Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010029333 Neurosis Diseases 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 206010034719 Personality change Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 206010039987 Senile psychosis Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000000573 anti-seizure effect Effects 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 108700039855 mouse a Proteins 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/554,177 US4115570A (en) | 1975-02-28 | 1975-02-28 | Morpholine compounds and methods of use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621540A5 true CH621540A5 (OSRAM) | 1981-02-13 |
Family
ID=24212328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH58676A CH621540A5 (OSRAM) | 1975-02-28 | 1976-01-19 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4115570A (OSRAM) |
| JP (1) | JPS5725036B2 (OSRAM) |
| BE (1) | BE838848A (OSRAM) |
| CA (1) | CA1069897A (OSRAM) |
| CH (1) | CH621540A5 (OSRAM) |
| DE (1) | DE2559072A1 (OSRAM) |
| ES (1) | ES445543A1 (OSRAM) |
| FR (1) | FR2302086A1 (OSRAM) |
| GB (1) | GB1536464A (OSRAM) |
| MX (1) | MX3603E (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190601B (it) * | 1986-01-27 | 1988-02-16 | Cometec Srl | Derivati della morfolina,loro uso quali stimolanti di crescita negli animali e procedimento per la loro preparazione |
| EP0300325B1 (en) * | 1987-07-20 | 1993-06-16 | COMETEC S.r.l. | Compositions for promoting growth of animals |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH83A (fr) * | 1888-11-17 | 1889-01-10 | Fontainemelon Horlogerie | Perfectionnements apportés à la construction des montres de tous calibres |
| US2851494A (en) * | 1955-03-04 | 1958-09-09 | Hoechst Ag | New alpha-amino-beta-hydroxycarboxylic acid amides and a process of preparing them |
| BE758380A (fr) * | 1969-11-04 | 1971-04-16 | Sumitomo Chemical Co | Procede de preparation de derives d'aryl-cetones |
-
1975
- 1975-02-28 US US05/554,177 patent/US4115570A/en not_active Expired - Lifetime
- 1975-12-30 DE DE19752559072 patent/DE2559072A1/de not_active Ceased
-
1976
- 1976-01-19 CH CH58676A patent/CH621540A5/it not_active IP Right Cessation
- 1976-02-03 MX MX761771U patent/MX3603E/es unknown
- 1976-02-18 GB GB6474/76A patent/GB1536464A/en not_active Expired
- 1976-02-23 BE BE164558A patent/BE838848A/xx not_active IP Right Cessation
- 1976-02-25 CA CA246,532A patent/CA1069897A/en not_active Expired
- 1976-02-26 ES ES445543A patent/ES445543A1/es not_active Expired
- 1976-02-27 JP JP2204176A patent/JPS5725036B2/ja not_active Expired
- 1976-02-27 FR FR7605625A patent/FR2302086A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51110533A (OSRAM) | 1976-09-30 |
| FR2302086A1 (fr) | 1976-09-24 |
| BE838848A (fr) | 1976-06-16 |
| JPS5725036B2 (OSRAM) | 1982-05-27 |
| DE2559072A1 (de) | 1976-09-02 |
| CA1069897A (en) | 1980-01-15 |
| MX3603E (es) | 1981-03-30 |
| GB1536464A (en) | 1978-12-20 |
| AU1090276A (en) | 1977-02-17 |
| FR2302086B1 (OSRAM) | 1979-09-28 |
| ES445543A1 (es) | 1977-11-01 |
| US4115570A (en) | 1978-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4138492A (en) | Aromatic amides of heterocyclic compounds and therapeutic compositions containing same | |
| DE3877406T2 (de) | Benzothiazolinon-derivate, ihre herstellung und pharmazeutische zusammensetzung. | |
| CA2695742C (en) | Bicyclic amides for enhancing glutamatergic synaptic responses | |
| EP0272052B1 (en) | Anxiolytic-N-(1-Azabicyclo[2.2.2]Oct-3-yl) Benzamides and Thobenzamides | |
| IE47798B1 (en) | Substituted ortho-anisamides,methods of preparing them,compositions containing them and their application as psychotropic agents | |
| EP0830863A1 (de) | Die gastrointestinale Durchblutung fördernde Arzneimittel | |
| US4599355A (en) | Treatment of sleep disorders | |
| EP2233140A1 (en) | Bicyclic amides for enhancing glutamatergic synaptic responses | |
| DE2701854A1 (de) | Hypolipidaemische p-benzylaminobenzoesaeuren und sie enthaltende mittel | |
| AU614768B2 (en) | 2-alkoxy-N-(1-azabicyclo(2.2.2)oct-3-yl) benzamides and thiobenzamides | |
| FI60200C (fi) | Foerfarande foer framstaellning av farmakologiskt vaerdefulla n-arylalkylpiperidylsubstituerade bensamider | |
| US4011330A (en) | Vincaminic acid amides | |
| DE69412103T2 (de) | Polyamidsäure-derivate mit antigastrin wirkung, ihre herstellung und ihre verwendung als arzneimittel | |
| EP0330756B1 (de) | Thienotricyclen zur Behandlung von Erkrankungen der Bronchien | |
| DE2513136C3 (de) | N-(1-Benzylpiperid-4-yl)-benzamide, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate | |
| US4115570A (en) | Morpholine compounds and methods of use | |
| DE3222779C2 (OSRAM) | ||
| WO1996002504A1 (de) | 6-biphenyloxymethyl-4-carboxy-2-piperidinone, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung | |
| RU2067979C1 (ru) | Производное аминобензойной кислоты или его фармацевтически приемлемая соль | |
| US4152519A (en) | 16-Hydroxy aspidospermidines and a process for their production | |
| JPH06279432A (ja) | 新規な化合物および該化合物を有効成分とする抗癌剤 | |
| US3639457A (en) | N-substituted-beta-oxybutyramide semisuccinate and its salt having effects of increasing paradoxical sleep and tranquillizing | |
| IT8922595A1 (it) | Agente colinergico, in particolare glicil-p-ammino-piridina-anilide- monoacetato, per il trattamento degli stati di demenza senile. | |
| JPS59141544A (ja) | ラクタムペプチド及びその製造方法、並びに該ペプチドを含有する医薬 | |
| KR950013764B1 (ko) | 피로글루타미드 유도체, 그 제조방법, 및 그것을 함유하는 치매증 치료제 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |