NO791979L - Fremgangsmaate for fremstilling av farmakologisk aktive forbindelser - Google Patents

Fremgangsmaate for fremstilling av farmakologisk aktive forbindelser

Info

Publication number: NO791979L
Authority: NO; Norway
Prior art keywords: methyl; formula; compound; alkyl; compounds
Prior art date: 1978-06-15

Application number

NO791979A

Other languages

English (en)

Norwegian (no)

Inventor

Fredrick Cassidy

Alexander Crossan Gouide

Original Assignee

Beecham Group Ltd

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.)

1978-06-15

Filing date

1979-06-14

Publication date

1979-12-18

1979-06-14 Application filed by Beecham Group Ltd filed Critical Beecham Group Ltd

1979-12-18 Publication of NO791979L publication Critical patent/NO791979L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 91
238000000034 method Methods 0.000 title claims description 31
238000002360 preparation method Methods 0.000 title claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
238000006243 chemical reaction Methods 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 5
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
238000007363 ring formation reaction Methods 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
229910021645 metal ion Inorganic materials 0.000 claims description 2
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
239000000243 solution Substances 0.000 description 37
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000007788 liquid Substances 0.000 description 15
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000725 suspension Substances 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
239000012267 brine Substances 0.000 description 10
230000000694 effects Effects 0.000 description 10
-1 hydroxymethylene Chemical group 0.000 description 10
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 9
229940091173 hydantoin Drugs 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000003937 drug carrier Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 7
230000000144 pharmacologic effect Effects 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000003921 oil Substances 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
238000003756 stirring Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
239000012230 colorless oil Substances 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
208000035475 disorder Diseases 0.000 description 5
235000009518 sodium iodide Nutrition 0.000 description 5
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000003826 tablet Substances 0.000 description 4
238000011282 treatment Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
OUYKHFMNDZGNBQ-UHFFFAOYSA-N 8-oxonon-2-enyl methanesulfonate Chemical compound CC(=O)CCCCC=CCOS(C)(=O)=O OUYKHFMNDZGNBQ-UHFFFAOYSA-N 0.000 description 2
JAPTYVTZNYWQTQ-UHFFFAOYSA-N 8-oxonon-2-ynyl methanesulfonate Chemical compound CC(=O)CCCCC#CCOS(C)(=O)=O JAPTYVTZNYWQTQ-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
206010006482 Bronchospasm Diseases 0.000 description 2
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 2
244000166102 Eucalyptus leucoxylon Species 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
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 2
241001465754 Metazoa Species 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
230000000767 anti-ulcer Effects 0.000 description 2
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
229910001863 barium hydroxide Inorganic materials 0.000 description 2
150000001602 bicycloalkyls Chemical group 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
150000001649 bromium compounds Chemical group 0.000 description 2
230000007885 bronchoconstriction Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000020176 deacylation Effects 0.000 description 2
238000005947 deacylation reaction Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
HADWSQKZZQKIDW-UHFFFAOYSA-N ethyl 2-acetyl-10-oxoundecanoate Chemical compound CCOC(=O)C(C(C)=O)CCCCCCCC(C)=O HADWSQKZZQKIDW-UHFFFAOYSA-N 0.000 description 2
WQQVUDKYAWITTN-UHFFFAOYSA-N ethyl 2-acetyl-2-bromo-10-oxoundecanoate Chemical compound CCOC(=O)C(Br)(C(C)=O)CCCCCCCC(C)=O WQQVUDKYAWITTN-UHFFFAOYSA-N 0.000 description 2
GLZHTBGHGFYQKV-UHFFFAOYSA-N ethyl 2-amino-10-oxoundec-4-enoate Chemical compound CCOC(=O)C(N)CC=CCCCCC(C)=O GLZHTBGHGFYQKV-UHFFFAOYSA-N 0.000 description 2
KUMZNNDJQPFLFN-UHFFFAOYSA-N ethyl 2-amino-10-oxoundec-4-ynoate Chemical compound CCOC(=O)C(N)CC#CCCCCC(C)=O KUMZNNDJQPFLFN-UHFFFAOYSA-N 0.000 description 2
XNQOZJPCOQEUIW-UHFFFAOYSA-N ethyl 2-bromo-10-oxoundecanoate Chemical compound CCOC(=O)C(Br)CCCCCCCC(C)=O XNQOZJPCOQEUIW-UHFFFAOYSA-N 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
229940094443 oxytocics prostaglandins Drugs 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium 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
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
150000003180 prostaglandins Chemical class 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
CDKBRFKCDOSWQZ-UHFFFAOYSA-N tert-butyl 2-acetyl-8-bromooctanoate Chemical compound CC(C)(C)OC(=O)C(C(=O)C)CCCCCCBr CDKBRFKCDOSWQZ-UHFFFAOYSA-N 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
229910052727 yttrium Inorganic materials 0.000 description 2
QXBHRWJUPKTHLH-UHFFFAOYSA-N (3-hydroxy-3-methylnonyl) 4-methylbenzenesulfonate Chemical compound CCCCCCC(C)(O)CCOS(=O)(=O)C1=CC=C(C)C=C1 QXBHRWJUPKTHLH-UHFFFAOYSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
DHUFMFSTBBYTIN-UHFFFAOYSA-N 1-amino-3-methylnonan-3-ol Chemical compound CCCCCCC(C)(O)CCN DHUFMFSTBBYTIN-UHFFFAOYSA-N 0.000 description 1
UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical class Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
KDQADQYAIVDJNP-UHFFFAOYSA-N 9-bromononan-2-one Chemical compound CC(=O)CCCCCCCBr KDQADQYAIVDJNP-UHFFFAOYSA-N 0.000 description 1
YSVSLBWGXSTLGK-UHFFFAOYSA-N 9-hydroxynon-7-en-2-one Chemical compound CC(=O)CCCCC=CCO YSVSLBWGXSTLGK-UHFFFAOYSA-N 0.000 description 1
RHWSAGDEMLORQN-UHFFFAOYSA-N 9-hydroxynon-7-yn-2-one Chemical compound CC(=O)CCCCC#CCO RHWSAGDEMLORQN-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
244000144725 Amygdalus communis Species 0.000 description 1
235000011437 Amygdalus communis Nutrition 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
206010067482 No adverse event Diseases 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
235000020224 almond Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
230000003509 anti-fertility effect Effects 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000007883 bronchodilation Effects 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000005792 cardiovascular activity Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000011109 contamination Methods 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
HPHIIEUECTTZNU-UHFFFAOYSA-N ethyl 2-[(3-cyclohexyl-3-hydroxybutyl)amino]-10-oxoundecanoate Chemical compound CC(=O)CCCCCCCC(C(=O)OCC)NCCC(C)(O)C1CCCCC1 HPHIIEUECTTZNU-UHFFFAOYSA-N 0.000 description 1
OIVRFTWNBDYCEN-UHFFFAOYSA-N ethyl 2-[(3-hydroxy-3-methylnonyl)amino]-10-oxoundec-4-enoate Chemical compound CCCCCCC(C)(O)CCNC(C(=O)OCC)CC=CCCCCC(C)=O OIVRFTWNBDYCEN-UHFFFAOYSA-N 0.000 description 1
DQNJOAKVPCFNJQ-UHFFFAOYSA-N ethyl 2-[(5-cyclohexyl-3-hydroxy-3-methylpentyl)amino]-10-oxoundecanoate Chemical compound CC(=O)CCCCCCCC(C(=O)OCC)NCCC(C)(O)CCC1CCCCC1 DQNJOAKVPCFNJQ-UHFFFAOYSA-N 0.000 description 1
NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical class CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
201000005917 gastric ulcer Diseases 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000002997 prostaglandinlike Effects 0.000 description 1
230000001007 puffing effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
238000007789 sealing Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 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
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO791979A 1978-06-15 1979-06-14 Fremgangsmaate for fremstilling av farmakologisk aktive forbindelser NO791979L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7827019		1978-06-15

Publications (1)

Publication Number	Publication Date
NO791979L true NO791979L (no)	1979-12-18

Family

ID=10497983

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO791979A NO791979L (no)	1978-06-15	1979-06-14	Fremgangsmaate for fremstilling av farmakologisk aktive forbindelser

Country Status (12)

Country	Link
US (1)	US4241074A (de)
EP (1)	EP0006353B1 (de)
JP (1)	JPS554388A (de)
AT (1)	ATE1422T1 (de)
AU (1)	AU4778279A (de)
DE (1)	DE2963476D1 (de)
DK (1)	DK249479A (de)
ES (1)	ES481603A1 (de)
IL (1)	IL57505A0 (de)
NO (1)	NO791979L (de)
PT (1)	PT69750A (de)
ZA (1)	ZA792977B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA802765B (en) *	1979-05-23	1981-05-27	Beecham Group Ltd	Novel compounds
US4496577A (en) *	1983-10-05	1985-01-29	Syntex (U.S.A.) Inc.	Imidazolidinone prostaglandins, compositions and use
GB8417863D0 (en) *	1984-07-13	1984-08-15	Lucas Ind Plc	Fuel pumping apparatus
US4746755A (en) *	1986-05-06	1988-05-24	The Dow Chemical Company	Preparation of hydrantoic acids and hydantoins

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2323193A1 (de) *	1972-05-10	1973-11-22	Du Pont	Pyrazolidinone
DE2451160A1 (de) *	1973-10-30	1975-05-07	Du Pont	3-pyrazolidinone und pyrazolidine
DK244577A (da) *	1976-06-03	1977-12-04	Wellcome Found	Fremgangsmade til fremstilling af hydantoinderivater
IL53559A0 (en) *	1976-12-18	1978-03-10	Beecham Group Ltd	Novel prostaglandin analogues their preparation and pharmaceutical compositions containing them
US4152445A (en) *	1976-12-18	1979-05-01	Beecham Group Limited	1-(3-Hydroxyalk-1-yl)-5-(carboxyalkyl)hydantoin derivatives
GB1598073A (en) *	1976-12-18	1981-09-16	Beecham Group Ltd	8,10,12-triazaprostaglandins
JPS5463083A (en) *	1977-09-05	1979-05-21	Wellcome Found	Organism active nitrogen compound

1979
- 1979-06-05 AU AU47782/79A patent/AU4778279A/en not_active Abandoned
- 1979-06-06 IL IL57505A patent/IL57505A0/xx unknown
- 1979-06-11 PT PT69750A patent/PT69750A/pt unknown
- 1979-06-14 US US06/048,514 patent/US4241074A/en not_active Expired - Lifetime
- 1979-06-14 DE DE7979301145T patent/DE2963476D1/de not_active Expired
- 1979-06-14 EP EP79301145A patent/EP0006353B1/de not_active Expired
- 1979-06-14 DK DK249479A patent/DK249479A/da not_active Application Discontinuation
- 1979-06-14 NO NO791979A patent/NO791979L/no unknown
- 1979-06-14 AT AT79301145T patent/ATE1422T1/de not_active IP Right Cessation
- 1979-06-15 JP JP7556779A patent/JPS554388A/ja active Pending
- 1979-06-15 ZA ZA792977A patent/ZA792977B/xx unknown
- 1979-06-15 ES ES481603A patent/ES481603A1/es not_active Expired

Also Published As

Publication number	Publication date
ZA792977B (en)	1980-06-25
IL57505A0 (en)	1979-10-31
DK249479A (da)	1979-12-16
AU4778279A (en)	1979-12-20
JPS554388A (en)	1980-01-12
ES481603A1 (es)	1980-06-16
ATE1422T1 (de)	1982-08-15
PT69750A (en)	1979-07-01
EP0006353A1 (de)	1980-01-09
EP0006353B1 (de)	1982-08-04
DE2963476D1 (en)	1982-09-30
US4241074A (en)	1980-12-23

Publication	Publication Date	Title
US5891906A (en)	1999-04-06	Polyacetate-derived phorboids having anti-inflammatory and other uses
IE51882B1 (en)	1987-04-15	1,2,2-triphenyl but-1-ene derivatives as well as a method for their production and their use as a pharmaceutical preparation
EP0125783A1 (de)	1984-11-21	Dopamin-beta-hydroxylase Inhibitoren
US5716968A (en)	1998-02-10	Protein kinase C modulators. H.
ZA200206344B (en)	2003-09-19	Ocular hypotensive lipids.
US5750568A (en)	1998-05-12	Protein kinase C Modulators. L.
EP0482183B1 (de)	1997-07-30	Histamin-h3-rezeptor-agonisten zur therapeutischen anwendung, pharmazeutische zubereitungen, die an h3-rezeptoren-agonistisch wirken, un die methode ihrer darstellung
US4077999A (en)	1978-03-07	Novel oxime ethers
CS219943B2 (en)	1983-03-25	Method of making the racemic and optically unite derivatives of the 1-phenyl-2-cyclohexene-1-alcylamine
NO791979L (no)	1979-12-18	Fremgangsmaate for fremstilling av farmakologisk aktive forbindelser
DE2333847A1 (de)	1974-01-24	Tetrahydronaphthole, ihre salze und diese verbindungen enthaltende arzneimittel
US4294972A (en)	1981-10-13	1,2-Disubstituted oxo triazolidine
CA2040058C (en)	2001-10-23	Alpha-mannosidase and fucosidase inhibitors
US5886019A (en)	1999-03-23	Protein kinase C modulators. F.
US4138407A (en)	1979-02-06	2,4 Pyrrolidinediones
EP0003410B1 (de)	1982-10-06	Hydantoine und Thiohydantoine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
US4851416A (en)	1989-07-25	Berban derivatives as α2 -adrenergic antagonists
US4237131A (en)	1980-12-02	Prostaglandin analogues
US4544665A (en)	1985-10-01	1-Aryl-3-azabicyclo[3.2.0]heptanes
US4156730A (en)	1979-05-29	Pharmaceutically active compounds, preparation thereof, intermediates useful in such preparation and compositions containing the compounds
NO763566L (de)	1977-04-26
CA1209586A (en)	1986-08-12	Naphthalenecarboxamides, their production and use
JP3888397B2 (ja)	2007-02-28	イソプレン誘導体
WO2008088937A1 (en)	2008-07-24	Quinolynylmethylimidizoles as therapeutic agents
GB1598662A (en)	1981-09-23	10,12-diazoprostaglandins