BE673597A - - Google Patents

Info

Publication number: BE673597A
Authority: BE; Belgium
Prior art keywords: acid; chosen; carbon atoms; composition; toxic
Prior art date: 1963-01-28

Application number

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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.)

1963-01-28

Filing date

1965-12-10

Publication date

1966-04-01

1963-01-28 Priority claimed from US254459A external-priority patent/US3194733A/en

1965-12-10 Application filed filed Critical

1966-04-01 Publication of BE673597A publication Critical patent/BE673597A/fr

Links

239000002253 acid Substances 0.000 claims description 78
-1 acids long chain fatty acids Chemical class 0.000 claims description 53
239000000203 mixture Substances 0.000 claims description 46
150000002148 esters Chemical class 0.000 claims description 42
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 31
238000000034 method Methods 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 17
150000002314 glycerols Chemical class 0.000 claims description 12
239000007788 liquid Substances 0.000 claims description 12
238000007911 parenteral administration Methods 0.000 claims description 10
150000004668 long chain fatty acids Chemical class 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
230000002035 prolonged effect Effects 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
229950000688 phenothiazine Drugs 0.000 claims description 4
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 3
AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims description 3
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 3
150000002384 heptanoic acid esters Chemical class 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims 11
230000003000 nontoxic effect Effects 0.000 claims 11
235000015112 vegetable and seed oil Nutrition 0.000 claims 11
239000008158 vegetable oil Substances 0.000 claims 11
208000020016 psychiatric disease Diseases 0.000 claims 10
230000000694 effects Effects 0.000 claims 6
125000006182 dimethyl benzyl group Chemical group 0.000 claims 4
125000003944 tolyl group Chemical group 0.000 claims 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
125000004429 atom Chemical group 0.000 claims 3
229910052799 carbon Inorganic materials 0.000 claims 3
235000014113 dietary fatty acids Nutrition 0.000 claims 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
208000035475 disorder Diseases 0.000 claims 2
239000000194 fatty acid Substances 0.000 claims 2
229930195729 fatty acid Natural products 0.000 claims 2
150000004665 fatty acids Chemical class 0.000 claims 2
230000003340 mental effect Effects 0.000 claims 2
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
239000003921 oil Substances 0.000 description 17
235000019198 oils Nutrition 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
230000008569 process Effects 0.000 description 15
239000000243 solution Substances 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
239000007787 solid Substances 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
150000007513 acids Chemical class 0.000 description 8
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
150000001263 acyl chlorides Chemical class 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
235000021355 Stearic acid Nutrition 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 5
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
239000008117 stearic acid Substances 0.000 description 5
MUXPPYATEKVUBJ-UHFFFAOYSA-N 2,2-diethylbutanoyl chloride Chemical compound CCC(CC)(CC)C(Cl)=O MUXPPYATEKVUBJ-UHFFFAOYSA-N 0.000 description 4
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 4
HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
150000001735 carboxylic acids Chemical group 0.000 description 4
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 4
UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
150000002990 phenothiazines Chemical class 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000008159 sesame oil Substances 0.000 description 4
235000011803 sesame oil Nutrition 0.000 description 4
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
BMUWVWPZSFOUDH-UHFFFAOYSA-N 2-bromoethyl heptanoate Chemical compound CCCCCCC(=O)OCCBr BMUWVWPZSFOUDH-UHFFFAOYSA-N 0.000 description 3
OFCPMJGTZUVUSM-UHFFFAOYSA-N 6-heptynoic acid Chemical compound OC(=O)CCCCC#C OFCPMJGTZUVUSM-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001266 acyl halides Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
239000000463 material Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
NIYFUCBYDXQQCX-UHFFFAOYSA-N 1-(2-bromoethoxy)ethanol Chemical compound CC(O)OCCBr NIYFUCBYDXQQCX-UHFFFAOYSA-N 0.000 description 2
RGVZHVOUTXEWKS-UHFFFAOYSA-N 12-methoxy-12-oxododec-10-enoic acid Chemical compound COC(=O)C=CCCCCCCCCC(O)=O RGVZHVOUTXEWKS-UHFFFAOYSA-N 0.000 description 2
RKGYJVASTMCSHZ-UHFFFAOYSA-N 2-(trifluoromethyl)-10H-phenothiazine Chemical compound C1=CC=C2NC3=CC(C(F)(F)F)=CC=C3SC2=C1 RKGYJVASTMCSHZ-UHFFFAOYSA-N 0.000 description 2
XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 2
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
125000005999 2-bromoethyl group Chemical group 0.000 description 2
YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical compound CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
GJWSUKYXUMVMGX-UHFFFAOYSA-N citronellic acid Chemical compound OC(=O)CC(C)CCC=C(C)C GJWSUKYXUMVMGX-UHFFFAOYSA-N 0.000 description 2
UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
LIZJAMAJAXTVJS-UHFFFAOYSA-N methyl 9-chloro-9-oxononanoate Chemical compound COC(=O)CCCCCCCC(Cl)=O LIZJAMAJAXTVJS-UHFFFAOYSA-N 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003204 tranquilizing agent Substances 0.000 description 2
230000002936 tranquilizing effect Effects 0.000 description 2
229960002703 undecylenic acid Drugs 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
HUTXVUPGARJNHM-UHFFFAOYSA-N 1-(2-chloroethoxy)ethanol Chemical compound CC(O)OCCCl HUTXVUPGARJNHM-UHFFFAOYSA-N 0.000 description 1
FAHUKNBUIVOJJR-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine Chemical compound C1=CC(F)=CC=C1C1C2=CC=CN2CCN1 FAHUKNBUIVOJJR-UHFFFAOYSA-N 0.000 description 1
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 description 1
RBBDPYXZGDGBSL-UHFFFAOYSA-N 2,3-dimethylnaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(O)=O)=C(C)C(C)=CC2=C1 RBBDPYXZGDGBSL-UHFFFAOYSA-N 0.000 description 1
MRUDNSFOFOQZDA-UHFFFAOYSA-N 2,6-dichlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC=C1Cl MRUDNSFOFOQZDA-UHFFFAOYSA-N 0.000 description 1
HCBHQDKBSKYGCK-UHFFFAOYSA-N 2,6-dimethylbenzoic acid Chemical compound CC1=CC=CC(C)=C1C(O)=O HCBHQDKBSKYGCK-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
KNBBDZULQFKSIE-UHFFFAOYSA-N 2-bromoethyl benzoate Chemical compound BrCCOC(=O)C1=CC=CC=C1 KNBBDZULQFKSIE-UHFFFAOYSA-N 0.000 description 1
UJRMHFPTLFNSTA-UHFFFAOYSA-N 2-chloro-2,2-diphenylacetic acid Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)O)C1=CC=CC=C1 UJRMHFPTLFNSTA-UHFFFAOYSA-N 0.000 description 1
NFHKZAUDRWRXMZ-UHFFFAOYSA-N 2-chloro-2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)Cl)C1=CC=CC=C1 NFHKZAUDRWRXMZ-UHFFFAOYSA-N 0.000 description 1
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical class OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
MTRYLAXNDGUFAK-UHFFFAOYSA-N 9-ethoxy-9-oxononanoic acid Chemical compound CCOC(=O)CCCCCCCC(O)=O MTRYLAXNDGUFAK-UHFFFAOYSA-N 0.000 description 1
VVWPSAPZUZXYCM-UHFFFAOYSA-N 9-methoxy-9-oxononanoic acid Chemical compound COC(=O)CCCCCCCC(O)=O VVWPSAPZUZXYCM-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229930008398 Citronellate Natural products 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
239000005639 Lauric acid Substances 0.000 description 1
IQQDLHGWGKEQDS-VOTSOKGWSA-N Methyl 2-heptenoate Chemical compound CCCC\C=C\C(=O)OC IQQDLHGWGKEQDS-VOTSOKGWSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
230000002716 ataractic effect 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
BCYXFRMDZWKZSF-SNAWJCMRSA-N beta-heptenoic acid Chemical compound CCC\C=C\CC(O)=O BCYXFRMDZWKZSF-SNAWJCMRSA-N 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
238000009835 boiling Methods 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
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
IDKVKKCZROPQSP-UHFFFAOYSA-N dec-2-ynoic acid Chemical compound CCCCCCCC#CC(O)=O IDKVKKCZROPQSP-UHFFFAOYSA-N 0.000 description 1
150000001954 decanoic acid esters Chemical class 0.000 description 1
IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 1
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004821 distillation Methods 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000008570 general process Effects 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
GYTGOLDQGRPDNF-UHFFFAOYSA-N hepta-2,4-dienoic acid Chemical compound CCC=CC=CC(O)=O GYTGOLDQGRPDNF-UHFFFAOYSA-N 0.000 description 1
UUBJKHVFGWGJKX-UHFFFAOYSA-N hydrate tetrahydrochloride Chemical compound O.Cl.Cl.Cl.Cl UUBJKHVFGWGJKX-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
URXZHQXYUFDGJO-UHFFFAOYSA-N methyl 11-chloro-11-oxoundecanoate Chemical compound COC(=O)CCCCCCCCCC(Cl)=O URXZHQXYUFDGJO-UHFFFAOYSA-N 0.000 description 1
RIZOOQYPYGPBOC-UHFFFAOYSA-N methyl 9-hydroxynonanoate Chemical compound COC(=O)CCCCCCCCO RIZOOQYPYGPBOC-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
IATZLNCRIIUXJM-UHFFFAOYSA-N methyl hept-2-ynoate Chemical compound CCCCC#CC(=O)OC IATZLNCRIIUXJM-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
ADLXTJMPCFOTOO-UHFFFAOYSA-N non-2-enoic acid Chemical compound CCCCCCC=CC(O)=O ADLXTJMPCFOTOO-UHFFFAOYSA-N 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
WEAGGGHXTMXZQA-UHFFFAOYSA-N octadec-2-ynoic acid Chemical compound CCCCCCCCCCCCCCCC#CC(O)=O WEAGGGHXTMXZQA-UHFFFAOYSA-N 0.000 description 1
WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
229950007538 pecazine Drugs 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
MISVOFAYXMKGCO-UHFFFAOYSA-M potassium;2,6-dimethylbenzoate Chemical compound [K+].CC1=CC=CC(C)=C1C([O-])=O MISVOFAYXMKGCO-UHFFFAOYSA-M 0.000 description 1
GRPLAIGLLKPFDZ-UHFFFAOYSA-M potassium;2-bromobenzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1Br GRPLAIGLLKPFDZ-UHFFFAOYSA-M 0.000 description 1
RNRNDNRVCAYZOP-UHFFFAOYSA-M potassium;2-chlorobenzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1Cl RNRNDNRVCAYZOP-UHFFFAOYSA-M 0.000 description 1
ZVUVJTQITHFYHV-UHFFFAOYSA-M potassium;naphthalene-1-carboxylate Chemical compound [K+].C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 ZVUVJTQITHFYHV-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
LZSRENODTOCXKJ-UHFFFAOYSA-M sodium;2,6-dichlorobenzoate Chemical compound [Na+].[O-]C(=O)C1=C(Cl)C=CC=C1Cl LZSRENODTOCXKJ-UHFFFAOYSA-M 0.000 description 1
NMTDPTPUELYEPL-UHFFFAOYSA-M sodium;heptanoate Chemical compound [Na+].CCCCCCC([O-])=O NMTDPTPUELYEPL-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
229940125725 tranquilizer Drugs 0.000 description 1
LGSNTPIHVYSXAV-UHFFFAOYSA-N tridec-2-ynoic acid Chemical compound CCCCCCCCCCC#CC(O)=O LGSNTPIHVYSXAV-UHFFFAOYSA-N 0.000 description 1
MZFGYVZYLMNXGL-UHFFFAOYSA-N undec-10-enoyl chloride Chemical compound ClC(=O)CCCCCCCCC=C MZFGYVZYLMNXGL-UHFFFAOYSA-N 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

BE673597D 1963-01-28 1965-12-10 BE673597A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US254459A US3194733A (en)	1961-04-26	1963-01-28	Phenothiazine compositions and method of treating mental disorders

Publications (1)

Publication Number	Publication Date
BE673597A true BE673597A (de)	1966-04-01

Family

ID=22964394

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE673597D BE673597A (de)	1963-01-28	1965-12-10

Country Status (1)

Country	Link
BE (1)	BE673597A (de)

1965
- 1965-12-10 BE BE673597D patent/BE673597A/fr unknown

Publication	Publication Date	Title
CH643546A5 (fr)	1984-06-15	Procede pour la preparation de derives d'hydantoine.
FR2526659A1 (fr)	1983-11-18	Medicaments immunomodulants a base de derives de l'acide phenylacetique
EP0015038A1 (de)	1980-09-03	Ein Diphenylhydantoin-Derivat enthaltende pharmazeutische Zusammensetzung, verwendete Derivate und ihre Herstellung
CH646967A5 (fr)	1984-12-28	Composes de pyranone et compositions pharmaceutiques les comprenant.
EP0459887A1 (de)	1991-12-04	Pyrazolyl-orthodialkyl-Benzamid-Derivate mit antikonvulsiver Aktivität, Verfahren zur Herstellung und pharmazeutische Zusammensetzung
EP0461958B1 (de)	1994-09-14	2-(Aminoalkyl)-5-(arylalkyl)1,3-dioxanderivate, ihre Herstellung und ihre Anwendung in der Therapeutik
EP0117771B1 (de)	1987-11-11	Imino-2-pyrrolidine, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
EP0231709B1 (de)	1992-07-22	Phenylnaphthyridine mit einer funktionellen Gruppe in Position 3, Verfahren zu ihrer Herstellung, diese enthaltende Arzneimittel besonders als Anti-Ulcus
EP0232659A1 (de)	1987-08-19	3-Methyl-substituierte Phenylnaphthyridine und diese enthaltende Arzneimittel
EP0122827B1 (de)	1986-07-23	1-(2-Ethoxycarbonyl-4-phenylalkylamido)-3-amino-2-Propanole, deren Herstellungen und deren pharmazeutische Verwendungen
FR2467840A1 (fr)	1981-04-30	Acides benzoyl-3 nitro-2 phenylacetiques et sels metalliques, amides et esters correspondants utiles notamment comme medicaments anti-inflammatoires compositions therapeutiques et formes pharmaceutiques les contenant et procedes et intermediaires pour leur preparation
EP0002978B1 (de)	1982-10-06	Thiazolidindion-2,4 Derivate, deren Herstellung und Verwendung als Arzneimittel
FR2631827A1 (fr)	1989-12-01	Nouveaux derives d'(hetero)aryl-5 tetrazole, leur procede de preparation et leur application en therapeutique
FR2534582A1 (fr)	1984-04-20	Nouveaux derives de benzofuranne et de benzothiophene, utiles comme agents anti-hyperuricemie et anti-hypertension, et leur procede de fabrication
CH447200A (fr)	1967-11-30	Procédé de préparation des acides carboxyliques a-substitués
BE884387A (fr)	1981-01-19	Composition a base d'acides aryloxyalkylaminobenzoiques, leurs sels et leurs esters
CH615414A5 (de)	1980-01-31
BE673597A (de)	1966-04-01
EP0196943B1 (de)	1990-01-24	8-Thiotetrahydrochinoleinderivate und deren Salze
BE779775A (fr)	1972-08-24	Derives de l'uree, procede pour les preparer et leurs applications
EP0176444B1 (de)	1989-02-22	Verfahren zur Herstellung von 4H-1,2,4-Triazol-Derivaten, so erhaltene neue Triazole, ihre Verwendung als Arzneimittel und sie enthaltende pharmazeutische Zusammensetzungen
EP0005385B1 (de)	1982-09-01	Piperazinmethanimin-Derivate, Verfahren zu ihrer Herstellung und ihre therapeutischen Verwendungen
CA1093582A (fr)	1981-01-13	Procede d'obtention de nouvelles propylenediamines
CH392483A (fr)	1965-05-31	Procédé de préparation de nouveaux esters d'acides 4-halo-3-sulfamoyl-benzoïques
CH639374A5 (fr)	1983-11-15	N-(4-pyrazolidinyl)-benzamides, presentant notamment des proprietes antiemetiques et de vidage gastrique.