CS240986B2 - Preparation method of 1-substitute spiro(imidazoline-4,3indolin)-2,2,5-triones and spirio(pyrrolidin-3,3-indolin)-2,3,5-triones - Google Patents

Preparation method of 1-substitute spiro(imidazoline-4,3indolin)-2,2,5-triones and spirio(pyrrolidin-3,3-indolin)-2,3,5-triones Download PDF

Info

Publication number: CS240986B2
Authority: CS; Czechoslovakia
Prior art keywords: process according; benzene ring; bromo; group; benzyl
Prior art date: 1982-12-20

Application number

CS839612A

Other languages

Czech (cs)

English (en)

Other versions

CS961283A2 (en

Inventor

Geoffrey R Bedford

David R 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

1986-03-13

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

1985-06-13 Publication of CS961283A2 publication Critical patent/CS961283A2/cs

1986-03-13 Publication of CS240986B2 publication Critical patent/CS240986B2/cs

Links

125000003003 spiro group Chemical group 0.000 title abstract description 8
238000002360 preparation method Methods 0.000 title description 8
239000000203 mixture Substances 0.000 claims abstract description 31
239000002904 solvent Substances 0.000 claims abstract description 11
239000003085 diluting agent Substances 0.000 claims abstract description 8
-1 1'-substituted spiro [imidazolidine-4,3'-indoline] - 2, 2 ', 5-trione Chemical class 0.000 claims description 39
238000000034 method Methods 0.000 claims description 28
150000001875 compounds Chemical class 0.000 claims description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
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 10
125000000217 alkyl group Chemical group 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 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
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
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 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
239000008096 xylene Substances 0.000 claims description 4
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 compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
229940093475 2-ethoxyethanol Drugs 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
125000006277 halobenzyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000006177 alkyl benzyl group Chemical group 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
238000010438 heat treatment Methods 0.000 abstract description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
150000003839 salts Chemical class 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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 11
229910052757 nitrogen Inorganic materials 0.000 description 11
239000007787 solid Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
125000001453 quaternary ammonium group Chemical group 0.000 description 7
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
235000011114 ammonium hydroxide Nutrition 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000000926 separation method Methods 0.000 description 5
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
239000000908 ammonium hydroxide Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
230000020477 pH reduction Effects 0.000 description 4
WAAPEIZFCHNLKK-UFBFGSQYSA-N (2s,4s)-6-fluoro-2',5'-dioxospiro[2,3-dihydrochromene-4,4'-imidazolidine]-2-carboxamide Chemical compound C([C@H](OC1=CC=C(F)C=C11)C(=O)N)[C@@]21NC(=O)NC2=O WAAPEIZFCHNLKK-UFBFGSQYSA-N 0.000 description 3
JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000001640 fractional crystallisation Methods 0.000 description 3
150000002391 heterocyclic compounds Chemical class 0.000 description 3
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 2
102000004316 Oxidoreductases Human genes 0.000 description 2
108090000854 Oxidoreductases Proteins 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
238000001311 chemical methods and process Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
239000003208 petroleum Substances 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
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
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 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
QKAWKVWXRHHPJG-UHFFFAOYSA-N (1-hydroxy-1-phenylpropan-2-yl)-trimethylazanium Chemical compound C[N+](C)(C)C(C)C(O)C1=CC=CC=C1 QKAWKVWXRHHPJG-UHFFFAOYSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
GPLYFNVWKDJGMF-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]spiro[2H-indole-3,4'-imidazolidine] Chemical compound ClC=1C=C(CN2CC3(NCNC3)C3=CC=CC=C23)C=CC1Cl GPLYFNVWKDJGMF-UHFFFAOYSA-N 0.000 description 1
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
YLVZMBDMNUAPOI-UHFFFAOYSA-N 1-phenylethylazanium;hydroxide Chemical compound [OH-].CC([NH3+])C1=CC=CC=C1 YLVZMBDMNUAPOI-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000238876 Acari Species 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
208000027472 Galactosemias Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
229940123934 Reductase inhibitor Drugs 0.000 description 1
UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000003851 azoles Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004803 chlorobenzyl group Chemical group 0.000 description 1
BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 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
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
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
125000006286 dichlorobenzyl group Chemical group 0.000 description 1
239000000539 dimer Substances 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000003480 eluent Substances 0.000 description 1
OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000003112 inhibitor Substances 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
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 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
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus 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
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
238000004064 recycling Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000003716 rejuvenation Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction 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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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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CS839612A 1982-12-20 1983-12-19 Preparation method of 1-substitute spiro(imidazoline-4,3indolin)-2,2,5-triones and spirio(pyrrolidin-3,3-indolin)-2,3,5-triones CS240986B2 (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number	Publication Date
CS961283A2 CS961283A2 (en)	1985-06-13
CS240986B2 true CS240986B2 (en)	1986-03-13

Family

ID=10535286

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS839612A CS240986B2 (en)	1982-12-20	1983-12-19	Preparation method of 1-substitute spiro(imidazoline-4,3indolin)-2,2,5-triones and spirio(pyrrolidin-3,3-indolin)-2,3,5-triones

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)	ES528173A0 (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
TW200801011A (en)	2006-02-07	2008-01-01	Astrazeneca Ab	New compounds II
US20090076049A1 (en) *	2006-02-07	2009-03-19	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
IE50332B1 (en) *	1979-11-13	1986-04-02	Ici Ltd	1'-substituted-spiro(imidazolidine-4,3'-indoline)-2,2',5-triones,processes for their manufacture and pharmaceutical compositions thereof
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 AU AU21852/83A patent/AU567312B2/en not_active Ceased
- 1983-11-30 ZA ZA838930A patent/ZA838930B/xx unknown
- 1983-12-07 AT AT83307446T patent/ATE30233T1/de not_active IP Right Cessation
- 1983-12-07 GR GR73172A patent/GR79707B/el unknown
- 1983-12-07 DE DE8383307446T patent/DE3374060D1/de not_active Expired
- 1983-12-07 EP EP83307446A patent/EP0115679B1/de not_active Expired
- 1983-12-15 DK DK579283A patent/DK579283A/da not_active Application Discontinuation
- 1983-12-16 FI FI834637A patent/FI834637A7/fi not_active Application Discontinuation
- 1983-12-16 DD DD83258088A patent/DD216935A5/de unknown
- 1983-12-19 PL PL24520383A patent/PL245203A1/xx unknown
- 1983-12-19 NO NO834687A patent/NO834687L/no unknown
- 1983-12-19 NZ NZ206619A patent/NZ206619A/en unknown
- 1983-12-19 HU HU834320A patent/HU189824B/hu unknown
- 1983-12-19 KR KR1019830005998A patent/KR840007407A/ko not_active Withdrawn
- 1983-12-19 ES ES528173A patent/ES528173A0/es active Granted
- 1983-12-19 CA CA000443630A patent/CA1209148A/en not_active Expired
- 1983-12-19 CS CS839612A patent/CS240986B2/cs unknown
- 1983-12-19 PT PT77848A patent/PT77848B/pt not_active IP Right Cessation
- 1983-12-20 JP JP58239004A patent/JPS59118787A/ja active Pending

Also Published As

Publication number	Publication date
CS961283A2 (en)	1985-06-13
ZA838930B (en)	1985-04-24
ATE30233T1 (de)	1987-10-15
AU2185283A (en)	1984-06-28
GR79707B (de)	1984-10-31
NZ206619A (en)	1986-09-10
IE56288B1 (en)	1991-06-05
CA1209148A (en)	1986-08-05
PT77848A (en)	1984-01-01
EP0115679A1 (de)	1984-08-15
DK579283A (da)	1984-06-21
IE832808L (en)	1984-06-20
JPS59118787A (ja)	1984-07-09
DK579283D0 (da)	1983-12-15
ES8600298A1 (es)	1985-10-01
EP0115679B1 (de)	1987-10-14
PL245203A1 (en)	1985-03-12
NO834687L (no)	1984-06-21
FI834637A7 (fi)	1984-06-21
AU567312B2 (en)	1987-11-19
KR840007407A (ko)	1984-12-07
DD216935A5 (de)	1985-01-02
ES528173A0 (es)	1985-10-01
PT77848B (en)	1986-07-11
GB8331194D0 (en)	1983-12-29
DE3374060D1 (en)	1987-11-19
FI834637A0 (fi)	1983-12-16
HU189824B (en)	1986-08-28

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NO167947B (no)	1991-09-16	Lagringsanordning for baand- eller plate-registreringsmedier
HU193941B (en)	1987-12-28	Process for production of 6-substituted-4-dialkil-tetra-hydrobenz/c,d/ indole derivatives
EP3424908A1 (de)	2019-01-09	Verfahren zur herstellung von levosimendan
CA2250062C (en)	2006-11-14	Method for obtaining pure enantiomers of a pyridazinone derivative
PL129212B1 (en)	1984-04-30	Process for preparing novel derivatives of substituted indolin-2-one
US4014890A (en)	1977-03-29	Process for preparing indole derivatives
CS240986B2 (en)	1986-03-13	Preparation method of 1-substitute spiro(imidazoline-4,3indolin)-2,2,5-triones and spirio(pyrrolidin-3,3-indolin)-2,3,5-triones
US4643999A (en)	1987-02-17	2-substituted imidazo[1,2-c]pyrimidines having anxiolytic properties
CS9100123A2 (en)	1991-09-15	Method of alkylated oxindole derivatives' stereoselective synthesis
NO742478L (de)	1975-02-10
US4611062A (en)	1986-09-09	Process for resolving certain spiro compounds
US20040181076A1 (en)	2004-09-16	Process for making ondansetron and intermediates thereof
US4567278A (en)	1986-01-28	Process for racemizing certain spiro compounds
PL106888B1 (pl)	1980-01-31	Sposob wytwarzania nowych amin pochodnych 2-fenylodwucyklooktanu i oktenu
Albright et al.	1986	Synthesis of 4‐aroyl‐5‐nitro‐1H‐imidazoles and 4‐aroyl‐5‐aminoimidazoles
SU1480771A3 (ru)	1989-05-15	Способ получени 9-амино-5,6,6 @ ,7-тетрагидро-4Н-бензо @ , @ тиазоло @ 4,5- @ хинолинов или их кислотно-аддитивных солей в виде рацемата, энантиомеров или смеси энантиомеров
FI78291B (fi)	1989-03-31	Foerfarande foer framstaellning av terapeutiskt anvaendbara 1-fenoxi-3-hydroxi-indolyl-alkylamino-3-propanoler.
JPH0633277B2 (ja)	1994-05-02	ベンゾチオピラノ〔４，３−ｃ〕ピリダジン化合物
CH685344A5 (fr)	1995-06-15	Dérivés de la benzofuranylimidazole, leur procédé de préparation ainsi qu'une composition thérapeutique les contenant.
JPS63502587A (ja)	1988-09-29	６位に環状基を含む置換基を有するインドロキノキサリン類
SU489334A3 (ru)	1975-10-25	Способ получени производных тиепина
JPH04352770A (ja)	1992-12-07	アミノアルキルチアゾール誘導体
CS208741B2 (en)	1981-09-15	Method of making the new derivatives of the 6,7-dimetoxyisochinolinacetamide