NO834687L - Fremgangsmaate for fremstilling av racemiske spiro imidazolin- eller pyrrolidin-indolin-derivater - Google Patents

Fremgangsmaate for fremstilling av racemiske spiro imidazolin- eller pyrrolidin-indolin-derivater

Info

Publication number: NO834687L
Authority: NO; Norway
Prior art keywords: compound; mixture; formula; benzyl; substituents
Prior art date: 1982-12-20

Application number

NO834687A

Other languages

English (en)

Norwegian (no)

Inventor

Geoffrey Robert Bedford

David Robert Brittain

Ronald Platt

Original Assignee

Ici Plc

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.)

1982-12-20

Filing date

1983-12-19

Publication date

1984-06-21

1983-12-19 Application filed by Ici Plc filed Critical Ici Plc

1984-06-21 Publication of NO834687L publication Critical patent/NO834687L/no

Links

238000000034 method Methods 0.000 title claims description 29
238000002360 preparation method Methods 0.000 title claims description 6
KCYRTFIGZYKOIT-UHFFFAOYSA-N 2,3-dihydro-1H-indole pyrrolidine Chemical class N1CCC2=CC=CC=C12.N1CCCC1 KCYRTFIGZYKOIT-UHFFFAOYSA-N 0.000 title 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 title 1
239000000203 mixture Substances 0.000 claims abstract description 35
238000010438 heat treatment Methods 0.000 claims abstract description 14
239000002904 solvent Substances 0.000 claims abstract description 13
239000003085 diluting agent Substances 0.000 claims abstract description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 43
-1 1-naphthylmethyl Chemical group 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 29
150000001875 compounds Chemical class 0.000 claims description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
150000002367 halogens Chemical group 0.000 claims description 11
125000001453 quaternary ammonium group Chemical group 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
239000012452 mother liquor Substances 0.000 claims description 7
230000020477 pH reduction Effects 0.000 claims description 7
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 4
238000001640 fractional crystallisation Methods 0.000 claims description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
239000008096 xylene Substances 0.000 claims description 4
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
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 claims description 3
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 claims description 3
229940057995 liquid paraffin Drugs 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 3
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical group CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
229940093475 2-ethoxyethanol Drugs 0.000 claims description 2
125000006177 alkyl benzyl group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
229940117389 dichlorobenzene Drugs 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
238000004064 recycling Methods 0.000 claims description 2
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims 2
125000003003 spiro group Chemical class 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
239000007787 solid Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 12
238000001914 filtration Methods 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
MDJHNFZNJNDPTM-UHFFFAOYSA-M trimethyl(1-phenylethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)C(C)C1=CC=CC=C1 MDJHNFZNJNDPTM-UHFFFAOYSA-M 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
238000000926 separation method Methods 0.000 description 4
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
102000016912 Aldehyde Reductase Human genes 0.000 description 3
108010053754 Aldehyde reductase Proteins 0.000 description 3
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
150000002391 heterocyclic compounds Chemical class 0.000 description 3
239000000463 material Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UNAPQFVJPRPFQU-UHFFFAOYSA-M (1-hydroxy-1-phenylpropan-2-yl)-trimethylazanium;hydroxide Chemical compound [OH-].C[N+](C)(C)C(C)C(O)C1=CC=CC=C1 UNAPQFVJPRPFQU-UHFFFAOYSA-M 0.000 description 2
BRJSPCMMRRKUON-UHFFFAOYSA-N 1'-[(3,4-dichlorophenyl)methyl]spiro[imidazolidine-5,3'-indole]-2,2',4-trione Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1C2=CC=CC=C2C2(C(NC(=O)N2)=O)C1=O BRJSPCMMRRKUON-UHFFFAOYSA-N 0.000 description 2
AOSJCERPVMLZFH-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]spiro[indole-3,3'-pyrrolidine]-2,2',5'-trione Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1C2=CC=CC=C2C2(C(NC(=O)C2)=O)C1=O AOSJCERPVMLZFH-UHFFFAOYSA-N 0.000 description 2
DHTZABNLHNWPEC-UHFFFAOYSA-N 1-[(4-bromo-2-fluorophenyl)methyl]-7-chloroindole-2,3-dione Chemical compound FC1=CC(Br)=CC=C1CN1C2=C(Cl)C=CC=C2C(=O)C1=O DHTZABNLHNWPEC-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
229940107816 ammonium iodide Drugs 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 1
JGYPKKCINQRZIQ-UHFFFAOYSA-N 1'-[(4-bromo-2-fluorophenyl)methyl]-7'-chlorospiro[imidazolidine-5,3'-indole]-2,2',4-trione Chemical compound FC1=CC(Br)=CC=C1CN1C2=C(Cl)C=CC=C2C2(C(NC(=O)N2)=O)C1=O JGYPKKCINQRZIQ-UHFFFAOYSA-N 0.000 description 1
SXYRTDICSOVQNZ-UHFFFAOYSA-N 1-(2-methoxyethoxy)ethanol Chemical compound COCCOC(C)O SXYRTDICSOVQNZ-UHFFFAOYSA-N 0.000 description 1
XMHNLZXYPAULDF-UHFFFAOYSA-N 4-bromo-1-(bromomethyl)-2-fluorobenzene Chemical compound FC1=CC(Br)=CC=C1CBr XMHNLZXYPAULDF-UHFFFAOYSA-N 0.000 description 1
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
MPLXQMMMGDYXIT-UHFFFAOYSA-N 7-chloro-1h-indole-2,3-dione Chemical compound ClC1=CC=CC2=C1NC(=O)C2=O MPLXQMMMGDYXIT-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
SJTSZVLGFLZBFK-HQBGAPFHSA-N C([C@H]([C@H](C1)C=C)C2)C[N+]1(C)[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N+]1(C)[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 SJTSZVLGFLZBFK-HQBGAPFHSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000027472 Galactosemias Diseases 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
238000005349 anion exchange Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 1
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
239000003480 eluent Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
125000006277 halobenzyl group Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
VCZILNWKBJBQGN-UHFFFAOYSA-N spiro[1h-indole-3,5'-imidazolidine]-2,2',4'-trione Chemical class N1C(=O)NC(=O)C21C1=CC=CC=C1NC2=O VCZILNWKBJBQGN-UHFFFAOYSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin

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Nitrogen Condensed Heterocyclic Rings (AREA)
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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Physical Or Chemical Processes And Apparatus (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Indole Compounds (AREA)
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NO834687A 1982-12-20 1983-12-19 Fremgangsmaate for fremstilling av racemiske spiro imidazolin- eller pyrrolidin-indolin-derivater NO834687L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB8236969		1982-12-20

Publications (1)

Publication Number	Publication Date
NO834687L true NO834687L (no)	1984-06-21

Family

ID=10535286

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO834687A NO834687L (no)	1982-12-20	1983-12-19	Fremgangsmaate for fremstilling av racemiske spiro imidazolin- eller pyrrolidin-indolin-derivater

Country Status (21)

Country	Link
EP (1)	EP0115679B1 (de)
JP (1)	JPS59118787A (de)
KR (1)	KR840007407A (de)
AT (1)	ATE30233T1 (de)
AU (1)	AU567312B2 (de)
CA (1)	CA1209148A (de)
CS (1)	CS240986B2 (de)
DD (1)	DD216935A5 (de)
DE (1)	DE3374060D1 (de)
DK (1)	DK579283A (de)
ES (1)	ES8600298A1 (de)
FI (1)	FI834637A7 (de)
GB (1)	GB8331194D0 (de)
GR (1)	GR79707B (de)
HU (1)	HU189824B (de)
IE (1)	IE56288B1 (de)
NO (1)	NO834687L (de)
NZ (1)	NZ206619A (de)
PL (1)	PL245203A1 (de)
PT (1)	PT77848B (de)
ZA (1)	ZA838930B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8415635D0 (en) *	1984-06-19	1984-07-25	Ici Plc	Cyclic amides
AR059265A1 (es)	2006-02-07	2008-03-19	Astrazeneca Ab	Compuestos espiro condensados con actividad inhibitoria en el receptor vaniloide1 (vr1)
WO2007091948A2 (en) *	2006-02-07	2007-08-16	Astrazeneca Ab	Novel spiro [imidazolidine-4, 3´-indole] 2, 2´,5´(1h) triones for treatment of conditions associated with vanilloid receptor 1

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3024231A (en) *	1959-02-11	1962-03-06	Spencer Chem Co	Racemization of d- and l-isomers of alpha-amino-epsilon-carprolactam
GB1569486A (en) *	1976-12-22	1980-06-18	Merck & Co Inc	Racemisationof 6-oxo-2-piperidine-carboxylic acid entantiomers
US4490381A (en) *	1979-11-13	1984-12-25	Imperial Chemical Industries Plc	1'-Substituted spiro[imidazolidine-4,3'-indoline]2,2',5-triones
IE53102B1 (en) *	1981-05-12	1988-06-22	Ici Plc	Pharmaceutical spiro-succinimide derivatives
GB8312379D0 (en) *	1983-05-05	1983-06-08	Ici Plc	Heterocyclic compounds

1983
- 1983-11-23 GB GB838331194A patent/GB8331194D0/en active Pending
- 1983-11-29 IE IE2808/83A patent/IE56288B1/en not_active IP Right Cessation
- 1983-11-30 ZA ZA838930A patent/ZA838930B/xx unknown
- 1983-11-30 AU AU21852/83A patent/AU567312B2/en not_active Ceased
- 1983-12-07 EP EP83307446A patent/EP0115679B1/de not_active Expired
- 1983-12-07 AT AT83307446T patent/ATE30233T1/de not_active IP Right Cessation
- 1983-12-07 DE DE8383307446T patent/DE3374060D1/de not_active Expired
- 1983-12-07 GR GR73172A patent/GR79707B/el unknown
- 1983-12-15 DK DK579283A patent/DK579283A/da not_active Application Discontinuation
- 1983-12-16 DD DD83258088A patent/DD216935A5/de unknown
- 1983-12-16 FI FI834637A patent/FI834637A7/fi not_active Application Discontinuation
- 1983-12-19 NO NO834687A patent/NO834687L/no unknown
- 1983-12-19 PL PL24520383A patent/PL245203A1/xx unknown
- 1983-12-19 ES ES528173A patent/ES8600298A1/es not_active Expired
- 1983-12-19 CS CS839612A patent/CS240986B2/cs unknown
- 1983-12-19 KR KR1019830005998A patent/KR840007407A/ko not_active Withdrawn
- 1983-12-19 HU HU834320A patent/HU189824B/hu unknown
- 1983-12-19 NZ NZ206619A patent/NZ206619A/en unknown
- 1983-12-19 PT PT77848A patent/PT77848B/pt not_active IP Right Cessation
- 1983-12-19 CA CA000443630A patent/CA1209148A/en not_active Expired
- 1983-12-20 JP JP58239004A patent/JPS59118787A/ja active Pending

Also Published As

Publication number	Publication date
AU567312B2 (en)	1987-11-19
IE56288B1 (en)	1991-06-05
DE3374060D1 (en)	1987-11-19
PL245203A1 (en)	1985-03-12
IE832808L (en)	1984-06-20
GB8331194D0 (en)	1983-12-29
CS240986B2 (en)	1986-03-13
EP0115679B1 (de)	1987-10-14
DD216935A5 (de)	1985-01-02
KR840007407A (ko)	1984-12-07
PT77848B (en)	1986-07-11
ATE30233T1 (de)	1987-10-15
GR79707B (de)	1984-10-31
FI834637A7 (fi)	1984-06-21
DK579283A (da)	1984-06-21
NZ206619A (en)	1986-09-10
FI834637A0 (fi)	1983-12-16
EP0115679A1 (de)	1984-08-15
CS961283A2 (en)	1985-06-13
PT77848A (en)	1984-01-01
CA1209148A (en)	1986-08-05
DK579283D0 (da)	1983-12-15
ES528173A0 (es)	1985-10-01
JPS59118787A (ja)	1984-07-09
ES8600298A1 (es)	1985-10-01
HU189824B (en)	1986-08-28
AU2185283A (en)	1984-06-28
ZA838930B (en)	1985-04-24

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US5247102A (en)	1993-09-21	Process for the preparation of substituted isoflavone derivative
NO154346B (no)	1986-05-26	Analogifremgangsmaate for fremstilling av terapeutisk aktive ftalazin-4-yl-eddiksyrederivater.
NO162176B (no)	1989-08-14	Middel for bekjempelse av plantesykdommer og anvendelse derav.
US4490381A (en)	1984-12-25	1'-Substituted spiro[imidazolidine-4,3'-indoline]2,2',5-triones
EP2479176B1 (de)	2014-09-17	Verfahren zur herstellung von iloperidon und verfahren zu seiner kristallisierung
NO821557L (no)	1982-11-15	Fremgangsmaate for fremstilling av spiro-pyrrolidin-indolin-derivater.
EP3619199A1 (de)	2020-03-11	Herstellung von 2-([1,2,3]triazol-2-yl)-benzoesäure-derivaten
GB2240104A (en)	1991-07-24	Arylvinylamide derivatives
NO764039L (de)	1977-06-06
EP0115679B1 (de)	1987-10-14	Chemisches Verfahren
EP2118058B1 (de)	2011-06-08	Verfahren zur herstellung von 5-benzyloxy-2-(4-benzyloxyphenyl)-3-methyl-1h-indol
US4611062A (en)	1986-09-09	Process for resolving certain spiro compounds
US4567278A (en)	1986-01-28	Process for racemizing certain spiro compounds
Portlock et al.	1973	Photocyclization of some 1-(haloarylmethyl) pyridinium salts
SU999967A3 (ru)	1983-02-23	Способ получени 6-N-замещенных 6-амино-3-пиридазинилгидразинов или их солей
EP0168181B1 (de)	1990-08-29	Zyklische Amide
US4806651A (en)	1989-02-21	Process for preparing 3,3-disubstituted indolines
Benincori et al.	1988	Rearrangements of aromatic carbonyl arylhydrazones of benzene, naphthalene, and azulene
NO841778L (no)	1984-11-06	Analogifremgangsmaate for fremstilling av et terapeutisk aktivt indolinderivat
US4595755A (en)	1986-06-17	5-halo-1,2,3-(1,2-dihydropyrrolo)-4-quinolones
NO168773B (no)	1991-12-23	Fremgangsmaate for spaltning av racemiske spiro-hydantoiner
CA2091183A1 (en)	1993-01-07	Process for producing indole derivatives
NO330342B1 (no)	2011-03-28	Ny fremgangsmate for fremstilling av imidazolylforbindelser
JPS60136556A (ja)	1985-07-20	ビスアミジンジフエニル誘導体およびそれらの製法