NO135277B - - Google Patents

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Info

Publication number: NO135277B
Authority: NO; Norway
Prior art keywords: group; ethyl; piperazine; formula; amino
Prior art date: 1971-08-05

Application number

NO2761/72A

Other languages

English (en)

Norwegian (no)

Other versions

NO135277C (xx

Inventor

J W Piskorz-Nalecki

Original Assignee

Stocznia Szczecinska

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.)

1971-08-05

Filing date

1972-08-03

Publication date

1976-12-06

1972-08-03 Application filed by Stocznia Szczecinska filed Critical Stocznia Szczecinska

1976-12-06 Publication of NO135277B publication Critical patent/NO135277B/no

1977-03-16 Publication of NO135277C publication Critical patent/NO135277C/no

Links

238000000034 method Methods 0.000 claims description 31
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 28
-1 carbamoylamino- Chemical class 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 9
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
150000002430 hydrocarbons Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical group OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims description 2
238000005804 alkylation reaction Methods 0.000 claims description 2
230000007717 exclusion Effects 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
150000004885 piperazines Chemical class 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
230000010933 acylation Effects 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
238000007083 alkoxycarbonylation reaction Methods 0.000 claims 1
238000002844 melting Methods 0.000 description 54
230000008018 melting Effects 0.000 description 54
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
239000000243 solution Substances 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
238000001953 recrystallisation Methods 0.000 description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
QUFYPJILXRCKSB-UHFFFAOYSA-N 1-ethyl-4-phenylpiperazine Chemical compound C1CN(CC)CCN1C1=CC=CC=C1 QUFYPJILXRCKSB-UHFFFAOYSA-N 0.000 description 17
238000010992 reflux Methods 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
239000007787 solid Substances 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
239000000706 filtrate Substances 0.000 description 12
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 11
229910000564 Raney nickel Inorganic materials 0.000 description 11
238000009835 boiling Methods 0.000 description 11
239000000047 product Substances 0.000 description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
239000012265 solid product Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000003921 oil Substances 0.000 description 8
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000002585 base Substances 0.000 description 6
239000003610 charcoal Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000012458 free base Substances 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
239000007868 Raney catalyst Substances 0.000 description 5
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
229910003446 platinum oxide Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
229910021626 Tin(II) chloride Inorganic materials 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
239000001119 stannous chloride Substances 0.000 description 4
235000011150 stannous chloride Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
238000010531 catalytic reduction reaction Methods 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
XNRTWORCVBKEMJ-UHFFFAOYSA-N 1-phenylpiperazin-1-ium;bromide Chemical compound Br.C1CNCCN1C1=CC=CC=C1 XNRTWORCVBKEMJ-UHFFFAOYSA-N 0.000 description 2
NQNZNONJZASOKL-UHFFFAOYSA-N 1-phenylpiperazin-4-ium;chloride Chemical compound Cl.C1CNCCN1C1=CC=CC=C1 NQNZNONJZASOKL-UHFFFAOYSA-N 0.000 description 2
SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 description 2
SUVHKJGVHFRTEA-UHFFFAOYSA-N 4-(2-bromoethyl)-1-methoxy-2-nitrobenzene Chemical compound COC1=CC=C(CCBr)C=C1[N+]([O-])=O SUVHKJGVHFRTEA-UHFFFAOYSA-N 0.000 description 2
UTDQPIXNPMGGPK-UHFFFAOYSA-N 4-(2-bromoethyl)aniline;hydrochloride Chemical compound Cl.NC1=CC=C(CCBr)C=C1 UTDQPIXNPMGGPK-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
230000022244 formylation Effects 0.000 description 2
238000006170 formylation reaction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
BVUUWWFHQIFUNM-UHFFFAOYSA-N n-[4-(4-chlorobutanoyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C(=O)CCCCl)C=C1 BVUUWWFHQIFUNM-UHFFFAOYSA-N 0.000 description 2
150000002828 nitro derivatives Chemical class 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
238000001665 trituration Methods 0.000 description 2
OXHPTABOQVHKLN-UHFFFAOYSA-N 1-(2-bromoethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCBr)C=C1 OXHPTABOQVHKLN-UHFFFAOYSA-N 0.000 description 1
NTURQZFFJDCTMZ-UHFFFAOYSA-N 1-(2-bromoethyl)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(CCBr)C=C1 NTURQZFFJDCTMZ-UHFFFAOYSA-N 0.000 description 1
PWZDJIUQHUGFRJ-UHFFFAOYSA-N 1-(2-chlorophenyl)piperazine Chemical compound ClC1=CC=CC=C1N1CCNCC1 PWZDJIUQHUGFRJ-UHFFFAOYSA-N 0.000 description 1
VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 1
KIFCSMQTGWVMOD-UHFFFAOYSA-N 1-(3-fluorophenyl)piperazine Chemical compound FC1=CC=CC(N2CCNCC2)=C1 KIFCSMQTGWVMOD-UHFFFAOYSA-N 0.000 description 1
KRLZPECRWPTVJR-UHFFFAOYSA-N 1-(4-chlorobut-2-enyl)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(CC=CCCl)C=C1 KRLZPECRWPTVJR-UHFFFAOYSA-N 0.000 description 1
AVJKDKWRVSSJPK-UHFFFAOYSA-N 1-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1N1CCNCC1 AVJKDKWRVSSJPK-UHFFFAOYSA-N 0.000 description 1
YFZHODLXYNDBSM-UHFFFAOYSA-N 1-ethenyl-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(C=C)C=C1 YFZHODLXYNDBSM-UHFFFAOYSA-N 0.000 description 1
NPLCIAUDODDVDO-UHFFFAOYSA-N 1-ethyl-4-phenylpiperazine;dihydrochloride Chemical compound Cl.Cl.C1CN(CC)CCN1C1=CC=CC=C1 NPLCIAUDODDVDO-UHFFFAOYSA-N 0.000 description 1
LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 1
VVZTUODWEYORTB-UHFFFAOYSA-N 2,6-dibromo-4-(2-bromoethyl)aniline Chemical compound NC1=C(Br)C=C(CCBr)C=C1Br VVZTUODWEYORTB-UHFFFAOYSA-N 0.000 description 1
JVMHULJEYUQYSH-UHFFFAOYSA-N 2-(4-nitrophenyl)ethylazanium;chloride Chemical compound Cl.NCCC1=CC=C([N+]([O-])=O)C=C1 JVMHULJEYUQYSH-UHFFFAOYSA-N 0.000 description 1
MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 description 1
WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 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
WNPSMKHXUKDOBN-UHFFFAOYSA-N 4-(2-bromoethyl)aniline Chemical compound NC1=CC=C(CCBr)C=C1 WNPSMKHXUKDOBN-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical compound ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 1
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
241000208202 Linaceae Species 0.000 description 1
235000004431 Linum usitatissimum Nutrition 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
238000000944 Soxhlet extraction Methods 0.000 description 1
229960001413 acetanilide Drugs 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
230000003474 anti-emetic effect Effects 0.000 description 1
239000002111 antiemetic agent Substances 0.000 description 1
229940125683 antiemetic agent Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000003193 general anesthetic agent Substances 0.000 description 1
229940005494 general anesthetics Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
229960002456 hexobarbital Drugs 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000003840 hydrochlorides Chemical class 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
CVVIJWRCGSYCMB-UHFFFAOYSA-N hydron;piperazine;dichloride Chemical compound Cl.Cl.C1CNCCN1 CVVIJWRCGSYCMB-UHFFFAOYSA-N 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63H—MARINE PROPULSION OR STEERING
- B63H25/00—Steering; Slowing-down otherwise than by use of propulsive elements; Dynamic anchoring, i.e. positioning vessels by means of main or auxiliary propulsive elements
- B63H25/06—Steering by rudders
- B63H25/38—Rudders
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B39/00—Equipment to decrease pitch, roll, or like unwanted vessel movements; Apparatus for indicating vessel attitude
- B63B39/06—Equipment to decrease pitch, roll, or like unwanted vessel movements; Apparatus for indicating vessel attitude to decrease vessel movements by using foils acting on ambient water

Landscapes

Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Combustion & Propulsion (AREA)
Mechanical Engineering (AREA)
Ocean & Marine Engineering (AREA)
Toys (AREA)
Earth Drilling (AREA)
Road Paving Structures (AREA)
Other Liquid Machine Or Engine Such As Wave Power Use (AREA)

NO276172A 1971-08-05 1972-08-03 NO135277C (xx)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PL14988171A PL77777B1 (xx)	1971-08-05	1971-08-05

Publications (2)

Publication Number	Publication Date
NO135277B true NO135277B (xx)	1976-12-06
NO135277C NO135277C (xx)	1977-03-16

Family

ID=19955280

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO276172A NO135277C (xx)	1971-08-05	1972-08-03

Country Status (10)

Country	Link
JP (1)	JPS5516880B1 (xx)
DE (1)	DE2236974C3 (xx)
FR (1)	FR2144501A7 (xx)
GB (1)	GB1395549A (xx)
NL (1)	NL7210715A (xx)
NO (1)	NO135277C (xx)
PL (1)	PL77777B1 (xx)
SE (1)	SE392596B (xx)
SU (1)	SU639437A3 (xx)
YU (1)	YU201272A (xx)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS62142800U (xx) *	1986-03-04	1987-09-09
JPS63174566U (xx) *	1986-12-22	1988-11-11
DE9113090U1 (de) *	1991-10-21	1992-01-16	Rochelt, Günter, Prof., 2000 Hamburg	Flügel oder flügelartiges Bauteil
GB2344333A (en) *	1998-12-04	2000-06-07	Barrus E P Ltd	Marine propulsion unit
KR100619302B1 (ko) *	2005-04-26	2006-09-06	현대중공업 주식회사	선박용 추력 날개
CN100348459C (zh) *	2005-11-17	2007-11-14	上海交通大学	十字型抗纵摇舵
DE202009009996U1 (de) *	2009-07-21	2010-12-02	Becker Marine Systems Gmbh & Co. Kg	Flossenruder für Wasserfahrzeuge
CN105644750B (zh) *	2016-03-16	2017-10-13	武汉理工大学	复合节能的江海直达船
JP7237718B2 (ja) *	2019-05-10	2023-03-13	三菱重工業株式会社	舵及びこれを備えた船舶

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB705439A (en) *	1951-10-31	1954-03-10	Heinrich Wilhelm Arthur Von Di	Improvements in propulsion devices for waterborne vessels

1971
- 1971-08-05 PL PL14988171A patent/PL77777B1/xx unknown
1972
- 1972-07-27 FR FR7227109A patent/FR2144501A7/fr not_active Expired
- 1972-07-27 DE DE19722236974 patent/DE2236974C3/de not_active Expired
- 1972-07-31 GB GB3567172A patent/GB1395549A/en not_active Expired
- 1972-07-31 SU SU721816507A patent/SU639437A3/ru active
- 1972-08-03 YU YU201272A patent/YU201272A/xx unknown
- 1972-08-03 SE SE1014472A patent/SE392596B/xx unknown
- 1972-08-03 NO NO276172A patent/NO135277C/no unknown
- 1972-08-04 NL NL7210715A patent/NL7210715A/xx not_active Application Discontinuation
- 1972-08-05 JP JP7871272A patent/JPS5516880B1/ja active Pending

Also Published As

Publication number	Publication date
SE392596B (sv)	1977-04-04
FR2144501A7 (xx)	1973-02-09
DE2236974C3 (de)	1975-09-18
NL7210715A (xx)	1973-02-07
GB1395549A (en)	1975-05-29
PL77777B1 (xx)	1975-04-30
YU201272A (en)	1981-06-30
JPS5516880B1 (xx)	1980-05-07
DE2236974A1 (de)	1973-02-15
DE2236974B2 (de)	1975-02-13
NO135277C (xx)	1977-03-16
SU639437A3 (ru)	1978-12-25

Publication	Publication Date	Title
US2985657A (en)	1961-05-23	1-(aroylalkyl)-4-heterocyclylpiperazines
NO118219B (xx)	1969-12-01
US3070606A (en)	1962-12-25	Xchxn
NO138979B (no)	1978-09-11	Engangsbleie.
NO135277B (xx)	1976-12-06
NO126734B (xx)	1973-03-19
US3170926A (en)	1965-02-23	N-phenylpiperazine compounds
US4672063A (en)	1987-06-09	Antiallergic 5-alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3-one compounds
NO137782B (no)	1978-01-16	Analogifremgangsm}te for fremstilling av nye farmakologisk aktive amino-fenyl-etanolaminer
NO152064B (no)	1985-04-15	Utvidet stiveranordning for en selvreisende vinge
Sperber et al.	1951	Histamine Antagonists. γ, γ-Disubstituted N, N-Dialkylpropylamines1
US3305553A (en)	1967-02-21	2-aminoquinazoline derivatives
US3267110A (en)	1966-08-16	Trifluoromethyl substituted o-aminophenyl ketones
US3823144A (en)	1974-07-09	N-(benzoyl)-n'-(piperazin-1-yl)alkyl)ureas
Ashley et al.	1958	673. The chemotherapy of schistosomiasis. Part I. Derivatives and analogues of αω-di-(p-aminophenoxy) alkanes
NO169961B (no)	1992-05-18	Analogifremgangsmaate for fremstilling av terapeutisk aktive piperaziner
RICE et al.	1958	Alkylation of Amines with Alcohols Catalyzed by Raney Nickel. II. Aliphatic Amines
US3773759A (en)	1973-11-20	1-arylideneamino-4-(2-oxo-3-phenyl-3-benzofuryl)piperazines
NO158185B (no)	1988-04-18	Analogifremgangsmaate ved fremstilling av terapeutisk aktive 1,5-difenylpyrazolin-3-on-forbindelser.
US3225031A (en)	1965-12-21	Phenyl-benzazepines and methods for their manufacture
Huckle et al.	1971	4-Amino-2, 3, 4, 5-tetrahydro-1-benzoxepin-5-ols, 4-amino-2, 3, 4, 5-tetrahydro-1-benzothiepin-5-ols, and related compounds
US3030367A (en)	1962-04-17	N -substituted derivatives of n-
DK145225B (da)	1982-10-11	Analogifremgangsmaade til fremstilling af 1-(3-trimethoxyphenoxy-2-hydroxy-propyl)-4-phenyl-piperazinderivater eller syreadditionssalte deraf
US3446806A (en)	1969-05-27	Process for the preparation of 1,4-benzodiazepine 4-oxides
US3089876A (en)	1963-05-14	1-(beta-aminoethyl)-4-(beta-hydroxyethyl)-piperazine