NO762781L - - Google Patents

Info

Publication number: NO762781L
Authority: NO; Norway
Prior art keywords: group; formula; hydrogen; parts; pharmaceutically acceptable
Prior art date: 1975-08-13

Application number

NO762781A

Other languages

English (en)

Norwegian (no)

Inventor

W Soudijn

I Van Wijngaarden

P A J Janssen

Original Assignee

Janssen Pharmaceutica Nv

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.)

1975-08-13

Filing date

1976-08-10

Publication date

1977-02-15

1976-06-21 Priority claimed from US05/697,813 external-priority patent/US4031226A/en

1976-08-10 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1977-02-15 Publication of NO762781L publication Critical patent/NO762781L/no

Links

239000000203 mixture Substances 0.000 claims description 87
150000001875 compounds Chemical class 0.000 claims description 86
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 74
229910052739 hydrogen Inorganic materials 0.000 claims description 56
239000001257 hydrogen Substances 0.000 claims description 56
239000002253 acid Substances 0.000 claims description 54
150000003839 salts Chemical class 0.000 claims description 49
238000000034 method Methods 0.000 claims description 48
125000000217 alkyl group Chemical group 0.000 claims description 39
238000006243 chemical reaction Methods 0.000 claims description 33
229910052736 halogen Inorganic materials 0.000 claims description 33
150000002367 halogens Chemical class 0.000 claims description 33
-1 1-methyl-2-pyrrolyl Chemical group 0.000 claims description 28
150000002431 hydrogen Chemical class 0.000 claims description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
150000003254 radicals Chemical class 0.000 claims description 23
239000003054 catalyst Substances 0.000 claims description 22
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
239000003795 chemical substances by application Substances 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
230000003474 anti-emetic effect Effects 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
230000000506 psychotropic effect Effects 0.000 claims description 11
239000003937 drug carrier Substances 0.000 claims description 10
239000000825 pharmaceutical preparation Substances 0.000 claims description 10
239000002111 antiemetic agent Substances 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
241001465754 Metazoa Species 0.000 claims description 8
206010047700 Vomiting Diseases 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 8
230000008673 vomiting Effects 0.000 claims description 8
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 7
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
238000010438 heat treatment Methods 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
150000003053 piperidines Chemical class 0.000 claims description 7
150000002148 esters Chemical group 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 6
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 5
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
238000005804 alkylation reaction Methods 0.000 claims description 5
WJMOWGFGRONZPA-UHFFFAOYSA-N aziridin-1-yl-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC1 WJMOWGFGRONZPA-UHFFFAOYSA-N 0.000 claims description 5
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
238000007363 ring formation reaction Methods 0.000 claims description 5
238000007910 systemic administration Methods 0.000 claims description 5
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
KLGQWSOYKYFBTR-UHFFFAOYSA-N 2-nitrobenzamide Chemical compound NC(=O)C1=CC=CC=C1[N+]([O-])=O KLGQWSOYKYFBTR-UHFFFAOYSA-N 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
150000005840 aryl radicals Chemical group 0.000 claims description 3
238000006114 decarboxylation reaction Methods 0.000 claims description 3
208000020016 psychiatric disease Diseases 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims 2
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 1
241000283707 Capra Species 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
FPRQPCRFHZFLJV-UHFFFAOYSA-N aziridin-1-yl-(2-chloro-4-fluorophenyl)methanone Chemical compound ClC1=C(C(=O)N2CC2)C=CC(=C1)F FPRQPCRFHZFLJV-UHFFFAOYSA-N 0.000 claims 1
HLGKHZJFZWYOPB-UHFFFAOYSA-N aziridin-1-yl-(2-chlorophenyl)methanone Chemical compound ClC1=CC=CC=C1C(=O)N1CC1 HLGKHZJFZWYOPB-UHFFFAOYSA-N 0.000 claims 1
150000003936 benzamides Chemical class 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
UNQSJPMSVIRLQE-UHFFFAOYSA-N iron piperidine Chemical compound [Fe].N1CCCCC1 UNQSJPMSVIRLQE-UHFFFAOYSA-N 0.000 claims 1
230000003340 mental effect Effects 0.000 claims 1
238000006722 reduction reaction Methods 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 66
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 48
238000002844 melting Methods 0.000 description 47
230000008018 melting Effects 0.000 description 47
239000000047 product Substances 0.000 description 47
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 39
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 37
229960001701 chloroform Drugs 0.000 description 37
239000003480 eluent Substances 0.000 description 26
239000000706 filtrate Substances 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
238000003756 stirring Methods 0.000 description 15
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 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
238000004440 column chromatography Methods 0.000 description 13
239000000543 intermediate Substances 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
238000001816 cooling Methods 0.000 description 12
238000010992 reflux Methods 0.000 description 12
239000007858 starting material Substances 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
239000002585 base Substances 0.000 description 10
239000000284 extract Substances 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
229910000564 Raney nickel Inorganic materials 0.000 description 8
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000000908 ammonium hydroxide Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 7
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
239000007868 Raney catalyst Substances 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 5
229960004046 apomorphine Drugs 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
239000003826 tablet Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
238000001035 drying Methods 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
201000004624 Dermatitis Diseases 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
208000010668 atopic eczema Diseases 0.000 description 3
239000012458 free base Substances 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
229940098462 oral drops Drugs 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000006187 pill Substances 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 2
KGGHWIKBOIQEAJ-UHFFFAOYSA-N 2-fluorobenzamide Chemical compound NC(=O)C1=CC=CC=C1F KGGHWIKBOIQEAJ-UHFFFAOYSA-N 0.000 description 2
NQMGZEFEQXWOAT-UHFFFAOYSA-N 4-fluoro-2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(F)=CC=C1C(Cl)=O NQMGZEFEQXWOAT-UHFFFAOYSA-N 0.000 description 2
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
150000001541 aziridines Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000002775 capsule Substances 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
239000003245 coal Substances 0.000 description 2
230000001351 cycling effect Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000010410 layer Substances 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
FWFRKOQCZMBNKS-UHFFFAOYSA-N n-(2-chloroethyl)furan-2-carboxamide Chemical compound ClCCNC(=O)C1=CC=CO1 FWFRKOQCZMBNKS-UHFFFAOYSA-N 0.000 description 2
SIUMVFGIULAFNI-UHFFFAOYSA-N n-(2-hydroxyethyl)pyridine-2-carboxamide Chemical compound OCCNC(=O)C1=CC=CC=N1 SIUMVFGIULAFNI-UHFFFAOYSA-N 0.000 description 2
150000002828 nitro derivatives Chemical class 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000001294 propane Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO762781A 1975-08-13 1976-08-10 NO762781L (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US60428275A	1975-08-13	1975-08-13
US05/697,813 US4031226A (en)	1975-08-13	1976-06-21	N-[(1-piperidinyl)alkyl]arylcarboxamide derivatives

Publications (1)

Publication Number	Publication Date
NO762781L true NO762781L (zh)	1977-02-15

Family

ID=27084629

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO762781A NO762781L (zh)	1975-08-13	1976-08-10

Country Status (16)

Country	Link
JP (1)	JPS5223080A (zh)
AT (1)	ATA601076A (zh)
BG (1)	BG24947A3 (zh)
DK (1)	DK365076A (zh)
ES (2)	ES450627A1 (zh)
FI (1)	FI762309A (zh)
HU (1)	HU175613B (zh)
IE (1)	IE43150B1 (zh)
IL (1)	IL50252A (zh)
IT (1)	IT1113286B (zh)
NO (1)	NO762781L (zh)
NZ (1)	NZ181717A (zh)
PH (1)	PH13757A (zh)
PL (1)	PL102727B1 (zh)
PT (1)	PT65471B (zh)
RO (1)	RO69420A (zh)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA841728B (en) *	1983-03-09	1984-11-28	Ciba Geigy Ag	Novel carboxamides

1976
- 1976-08-06 RO RO7687227A patent/RO69420A/ro unknown
- 1976-08-09 NZ NZ18171776A patent/NZ181717A/xx unknown
- 1976-08-10 PH PH18775A patent/PH13757A/en unknown
- 1976-08-10 NO NO762781A patent/NO762781L/no unknown
- 1976-08-11 PL PL19173876A patent/PL102727B1/pl unknown
- 1976-08-11 JP JP9501076A patent/JPS5223080A/ja active Pending
- 1976-08-11 ES ES450627A patent/ES450627A1/es not_active Expired
- 1976-08-12 DK DK365076A patent/DK365076A/da unknown
- 1976-08-12 IT IT5087576A patent/IT1113286B/it active
- 1976-08-12 FI FI762309A patent/FI762309A/fi not_active Application Discontinuation
- 1976-08-12 HU HU76JA765A patent/HU175613B/hu unknown
- 1976-08-12 AT AT601076A patent/ATA601076A/de not_active Application Discontinuation
- 1976-08-12 IL IL50252A patent/IL50252A/xx unknown
- 1976-08-12 IE IE178576A patent/IE43150B1/en unknown
- 1976-08-12 PT PT6547176A patent/PT65471B/pt unknown
- 1976-08-13 BG BG033993A patent/BG24947A3/xx unknown
1977
- 1977-07-29 ES ES461191A patent/ES461191A1/es not_active Expired

Also Published As

Publication number	Publication date
IL50252A (en)	1980-05-30
PT65471B (en)	1978-07-04
PH13757A (en)	1980-09-17
FI762309A (zh)	1977-02-14
ES461191A1 (es)	1978-06-16
ATA601076A (de)	1981-03-15
DK365076A (da)	1977-02-14
PL102727B1 (pl)	1979-04-30
IE43150B1 (en)	1980-12-31
IT1113286B (it)	1986-01-20
PT65471A (en)	1976-09-01
BG24947A3 (en)	1978-06-15
NZ181717A (en)	1979-01-11
IE43150L (en)	1977-02-13
JPS5223080A (en)	1977-02-21
ES450627A1 (es)	1978-01-01
IL50252A0 (en)	1976-10-31
RO69420A (ro)	1981-06-30
HU175613B (hu)	1980-09-28

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