NO770176L - Oksygererte n-aryl-diazacykler. - Google Patents

Oksygererte n-aryl-diazacykler.

Info

Publication number: NO770176L
Authority: NO; Norway
Prior art keywords: lower alkyl; formula; optionally; hydroxy; halogen
Prior art date: 1976-01-21

Application number

NO770176A

Other languages

English (en)

Norwegian (no)

Inventor

Kurt Eichenberger

Hans Kuehnis

Franz Ostermayer

Herbert Schroeter

Original Assignee

Ciba Geigy Ag

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.)

1976-01-21

Filing date

1977-01-20

Publication date

1977-07-22

1977-01-20 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1977-07-22 Publication of NO770176L publication Critical patent/NO770176L/no

Links

-1 cyan Chemical group 0.000 claims description 115
125000000217 alkyl group Chemical group 0.000 claims description 82
150000001875 compounds Chemical class 0.000 claims description 80
150000003839 salts Chemical class 0.000 claims description 57
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 49
229910052736 halogen Inorganic materials 0.000 claims description 41
150000002367 halogens Chemical class 0.000 claims description 40
125000003545 alkoxy group Chemical group 0.000 claims description 36
238000000034 method Methods 0.000 claims description 32
238000006243 chemical reaction Methods 0.000 claims description 22
239000007858 starting material Substances 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 15
238000012546 transfer Methods 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000003302 alkenyloxy group Chemical group 0.000 claims description 13
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 10
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 9
125000002947 alkylene group Chemical group 0.000 claims description 9
125000005133 alkynyloxy group Chemical group 0.000 claims description 9
125000001589 carboacyl group Chemical group 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 9
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 8
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
239000005977 Ethylene Substances 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000001624 naphthyl group Chemical group 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000002950 monocyclic group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 6
125000005236 alkanoylamino group Chemical group 0.000 claims description 5
125000002619 bicyclic group Chemical group 0.000 claims description 5
150000001356 alkyl thiols Chemical class 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 4
125000003700 epoxy group Chemical group 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000005281 alkyl ureido group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000002253 acid Substances 0.000 description 29
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
239000003054 catalyst Substances 0.000 description 21
239000000243 solution Substances 0.000 description 21
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
238000003756 stirring Methods 0.000 description 16
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 15
229910052794 bromium Inorganic materials 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
229910052801 chlorine Inorganic materials 0.000 description 15
229960004592 isopropanol Drugs 0.000 description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 13
239000000706 filtrate Substances 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
239000000284 extract Substances 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 9
150000002431 hydrogen Chemical class 0.000 description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
150000001340 alkali metals Chemical class 0.000 description 7
239000003638 chemical reducing agent Substances 0.000 description 7
238000001816 cooling Methods 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
239000003085 diluting agent Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000011261 inert gas Substances 0.000 description 6
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 6
231100000252 nontoxic Toxicity 0.000 description 6
230000003000 nontoxic effect Effects 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
239000000126 substance Substances 0.000 description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
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 5
239000013543 active substance Substances 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
239000002585 base Substances 0.000 description 5
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
239000000825 pharmaceutical preparation Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
WIDFNOIYHYOUQG-UHFFFAOYSA-N 1-phenyl-3-piperidin-4-ylimidazolidin-2-one Chemical compound O=C1N(C2CCNCC2)CCN1C1=CC=CC=C1 WIDFNOIYHYOUQG-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
125000005336 allyloxy group Chemical group 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
VCRYGHPVKURQMM-UHFFFAOYSA-N methane;platinum Chemical compound C.[Pt] VCRYGHPVKURQMM-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
235000011118 potassium hydroxide Nutrition 0.000 description 4
125000003373 pyrazinyl group Chemical group 0.000 description 4
239000011734 sodium Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
RJNVSQLNEALZLC-UHFFFAOYSA-N 2-[(2-methoxyphenoxy)methyl]oxirane Chemical compound COC1=CC=CC=C1OCC1OC1 RJNVSQLNEALZLC-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
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 3
241001465754 Metazoa Species 0.000 description 3
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003929 acidic solution Substances 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
OCIDXARMXNJACB-UHFFFAOYSA-N n'-phenylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=C1 OCIDXARMXNJACB-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
125000002098 pyridazinyl group Chemical group 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
230000009467 reduction Effects 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
229940100445 wheat starch Drugs 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
QRGZSIFEOIQAHE-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-3-(4-methoxyphenyl)imidazolidin-2-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)N(C2CCN(CC=3C=CC=CC=3)CC2)CC1 QRGZSIFEOIQAHE-UHFFFAOYSA-N 0.000 description 2
VGRGYZHTRQHSRL-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-3-phenylimidazolidin-2-one Chemical compound O=C1N(C2CCN(CC=3C=CC=CC=3)CC2)CCN1C1=CC=CC=C1 VGRGYZHTRQHSRL-UHFFFAOYSA-N 0.000 description 2
YLLORXQFHZAMRT-UHFFFAOYSA-N 1-(4-methoxyphenyl)ethane-1,2-diamine Chemical compound COC1=CC=C(C(N)CN)C=C1 YLLORXQFHZAMRT-UHFFFAOYSA-N 0.000 description 2
SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 description 2
125000005976 1-phenylethyloxy group Chemical group 0.000 description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
125000005975 2-phenylethyloxy group Chemical group 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-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
238000012404 In vitro experiment Methods 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
229910000272 alkali metal oxide Inorganic materials 0.000 description 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
125000005910 alkyl carbonate group Chemical group 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000001630 malic acid Substances 0.000 description 2
235000011090 malic acid Nutrition 0.000 description 2
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210000003975 mesenteric artery Anatomy 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
244000005700 microbiome Species 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
GJQNVZVOTKFLIU-UHFFFAOYSA-N piperidin-1-ium-4-one;chloride Chemical compound Cl.O=C1CCNCC1 GJQNVZVOTKFLIU-UHFFFAOYSA-N 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyridine Compounds (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO770176A 1976-01-21 1977-01-20 Oksygererte n-aryl-diazacykler. NO770176L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH70276		1976-01-21

Publications (1)

Publication Number	Publication Date
NO770176L true NO770176L (no)	1977-07-22

Family

ID=4193177

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO770176A NO770176L (no)	1976-01-21	1977-01-20	Oksygererte n-aryl-diazacykler.

Country Status (23)

Country	Link
US (1)	US4144344A (es)
JP (1)	JPS52105182A (es)
AT (1)	AT355570B (es)
AU (1)	AU512020B2 (es)
BE (1)	BE850556A (es)
CA (1)	CA1085398A (es)
DD (1)	DD129650A5 (es)
DE (1)	DE2701794A1 (es)
DK (1)	DK21777A (es)
ES (2)	ES455151A1 (es)
FI (1)	FI770190A7 (es)
FR (1)	FR2338940A1 (es)
GB (1)	GB1565902A (es)
GR (1)	GR62393B (es)
IE (1)	IE44276B1 (es)
IL (1)	IL51301A0 (es)
NL (1)	NL7700530A (es)
NO (1)	NO770176L (es)
NZ (1)	NZ183134A (es)
PL (1)	PL195461A1 (es)
PT (1)	PT66086B (es)
SE (1)	SE7700577L (es)
ZA (1)	ZA77336B (es)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4217350A (en) *	1976-01-21	1980-08-12	Ciba-Geigy Corporation	Oxygenated N-aryl-diazacyclic compounds
EP0000485A1 (de) *	1977-07-08	1979-02-07	Ciba-Geigy Ag	Piperidino-propanole, ihre Herstellung und pharmazeutische Präparate die diese enthalten
FI782133A7 (fi) *	1977-07-08	1979-01-09	Ciba Geigy Ag	Piperidino-propanoler och foerfarande foer deras framstaellning
US4314943A (en) *	1977-07-13	1982-02-09	Mead Johnson & Company	Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols
LU77856A1 (de) *	1977-07-27	1979-03-26	Ciba Geigy Ag	Verfahren zur herstellung von neuen piperidin-derivaten
US4304912A (en) *	1978-07-20	1981-12-08	Ciba-Geigy Corporation	Piperidine derivatives
US4495352A (en) *	1979-02-13	1985-01-22	Mead Johnson & Company	Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols
DE2905876A1 (de) *	1979-02-16	1980-08-28	Boehringer Mannheim Gmbh	Neue piperidinopropylderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
US4342761A (en) *	1979-11-01	1982-08-03	John Wyeth & Brother Limited	Piperidine derivatives
DE3066434D1 (en) *	1979-11-21	1984-03-08	Kyowa Hakko Kogyo Kk	Novel piperidine derivatives, method for the preparation thereof and pharmaceutical compositions containing them
US4344945A (en) *	1980-03-10	1982-08-17	Kyowa Hakko Kogyo Co., Ltd.	Piperidine derivatives
DE3324903A1 (de) *	1983-07-09	1985-01-17	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung substituierter ethylenharnstoffe sowie neue n-vinylethylenharnstoffe
US4816585A (en) *	1987-03-05	1989-03-28	Olin Corporation	Tetraalkylpiperidinyl substituted uracil derivatives and their use as ultraviolet light stabilizers
US4904714A (en) *	1987-10-02	1990-02-27	Olin Corporation	Synthetic resin composition and its method of use
FR2803298A1 (fr) *	1999-12-30	2001-07-06	Adir	Nouvelles urees lineaires ou cycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
MA33451B1 (fr) *	2009-06-26	2012-07-03	Novartis Ag	Dérivés d'imidazolidin-2-one 1,3-disubstitués en tant qu'inhibiteurs de cyp 17

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3459757A (en) *	1965-10-22	1969-08-05	American Cyanamid Co	Imidazolidines
US3956335A (en) *	1972-08-24	1976-05-11	Ciba-Geigy Corporation	1-Substituted-4-(2-oxo-1-imidazolidinyl) piperidines

1977
- 1977-01-18 DE DE19772701794 patent/DE2701794A1/de active Pending
- 1977-01-19 FR FR7701421A patent/FR2338940A1/fr active Granted
- 1977-01-19 PT PT66086A patent/PT66086B/pt unknown
- 1977-01-19 DD DD7700197003A patent/DD129650A5/xx unknown
- 1977-01-19 ES ES455151A patent/ES455151A1/es not_active Expired
- 1977-01-19 NL NL7700530A patent/NL7700530A/xx not_active Application Discontinuation
- 1977-01-19 CA CA270,045A patent/CA1085398A/en not_active Expired
- 1977-01-20 IE IE108/77A patent/IE44276B1/en unknown
- 1977-01-20 IL IL51301A patent/IL51301A0/xx unknown
- 1977-01-20 SE SE7700577A patent/SE7700577L/xx unknown
- 1977-01-20 NZ NZ183134A patent/NZ183134A/xx unknown
- 1977-01-20 AT AT33377A patent/AT355570B/de not_active IP Right Cessation
- 1977-01-20 BE BE174221A patent/BE850556A/xx unknown
- 1977-01-20 NO NO770176A patent/NO770176L/no unknown
- 1977-01-20 FI FI770190A patent/FI770190A7/fi not_active Application Discontinuation
- 1977-01-20 AU AU21491/77A patent/AU512020B2/en not_active Expired
- 1977-01-20 ZA ZA770336A patent/ZA77336B/xx unknown
- 1977-01-20 GB GB2312/77A patent/GB1565902A/en not_active Expired
- 1977-01-20 GR GR52610A patent/GR62393B/el unknown
- 1977-01-20 DK DK21777A patent/DK21777A/da not_active Application Discontinuation
- 1977-01-21 JP JP504377A patent/JPS52105182A/ja active Pending
- 1977-01-21 US US05/761,510 patent/US4144344A/en not_active Expired - Lifetime
- 1977-01-21 PL PL19546177A patent/PL195461A1/xx unknown
1978
- 1978-02-01 ES ES466532A patent/ES466532A1/es not_active Expired

Also Published As

Publication number	Publication date
AT355570B (de)	1980-03-10
NZ183134A (en)	1979-08-31
PT66086B (en)	1978-06-26
PL195461A1 (pl)	1978-12-18
PT66086A (en)	1977-02-01
AU512020B2 (en)	1980-09-18
AU2149177A (en)	1978-07-27
ATA33377A (de)	1979-08-15
DK21777A (da)	1977-07-22
FR2338940A1 (fr)	1977-08-19
ES455151A1 (es)	1978-04-16
CA1085398A (en)	1980-09-09
IE44276B1 (en)	1981-09-23
ZA77336B (en)	1977-11-30
SE7700577L (sv)	1977-07-22
JPS52105182A (en)	1977-09-03
IL51301A0 (en)	1977-03-31
GB1565902A (en)	1980-04-23
GR62393B (en)	1979-04-10
IE44276L (en)	1977-07-21
BE850556A (fr)	1977-07-20
NL7700530A (nl)	1977-07-25
ES466532A1 (es)	1978-10-01
DE2701794A1 (de)	1977-07-28
DD129650A5 (de)	1978-02-01
US4144344A (en)	1979-03-13
FR2338940B1 (es)	1980-03-14
FI770190A7 (es)	1977-07-22

Publication	Publication Date	Title
CA1095044A (en)	1981-02-03	N-piperid-4-yl benzamide compounds
DE69130597T2 (de)	1999-05-20	Arylalkylamine, Verfahren zur Herstellung und diese enthaltende Arzneimittel
AU756797B2 (en)	2003-01-23	Spiro-indolines as Y5 receptor antagonists
EP0533244B1 (en)	1997-12-17	Amide-substituted derivatives of spiroindanylcamphorsulfonyl oxytocin antagonists
DE69901934T2 (de)	2002-11-07	4-(2-keto-1-benzimidazolinyl)piperidin derivate als orl1-rezeptor agoniste
EP1175402B1 (en)	2005-07-20	Piperidine derivatives useful as ccr5 antagonists
RU2165933C2 (ru)	2001-04-27	Производные пиперазина, способ их получения, фармацевтическая композиция и способ лечения синдрома 8-oh-dpat
KR100258373B1 (ko)	2000-07-01	다환아민화합물및그의거울상이성질체,그의제조방법및이를함유하는제약학적조성물
US4835157A (en)	1989-05-30	Thieno- and furopyrimidine-2,4-dione piperidine derivatives as serotonin antagonists and alpha adrenergic blocking agents
US4144344A (en)	1979-03-13	Antihypertensive 1-substituted-4-(2-oxo-1-imidazolidinyl) piperidines
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