CH427800A - Procédé de préparation de nouveaux composés hétérocycliques - Google Patents

Procédé de préparation de nouveaux composés hétérocycliques

Info

Publication number: CH427800A
Authority: CH; Switzerland
Prior art keywords: group; formula; chloro; compounds; cycloalkyl
Prior art date: 1962-04-06

Application number

CH399263A

Other languages

English (en)

French (fr)

Inventor

Evan Lee Glyn

Robert Wragg William

Original Assignee

May & Baker 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.)

1962-04-06

Filing date

1963-03-29

Publication date

1967-01-15

1962-04-06 Priority claimed from GB1338962A external-priority patent/GB1012235A/en

1963-03-29 Application filed by May & Baker Ltd filed Critical May & Baker Ltd

1967-01-15 Publication of CH427800A publication Critical patent/CH427800A/fr

Links

238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims description 6
150000002391 heterocyclic compounds Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 21
-1 alkyl radicals Chemical class 0.000 claims description 15
125000005041 acyloxyalkyl group Chemical group 0.000 claims description 10
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
229910052783 alkali metal Inorganic materials 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000001188 haloalkyl group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000000460 chlorine Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
229940126062 Compound A Drugs 0.000 claims description 2
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
229910052731 fluorine Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
239000002253 acid Substances 0.000 description 25
230000008018 melting Effects 0.000 description 23
238000002844 melting Methods 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
BRONALLIAIBEPV-UHFFFAOYSA-N 4-(2-hydroxyethyl)isoindole-1,3-dione Chemical compound OCCC1=CC=CC2=C1C(=O)NC2=O BRONALLIAIBEPV-UHFFFAOYSA-N 0.000 description 13
150000003839 salts Chemical class 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
150000007513 acids Chemical class 0.000 description 11
150000002148 esters Chemical class 0.000 description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
150000001412 amines Chemical class 0.000 description 9
239000007787 solid Substances 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000001453 quaternary ammonium group Chemical group 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
229910019142 PO4 Inorganic materials 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
235000021317 phosphate Nutrition 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
239000002585 base Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
150000007519 polyprotic acids Polymers 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
HOCPDSKONPQIQM-UHFFFAOYSA-N 4-(2-bromoethyl)isoindole-1,3-dione Chemical compound BrCCC1=CC=CC2=C1C(=O)NC2=O HOCPDSKONPQIQM-UHFFFAOYSA-N 0.000 description 3
KHXUWBTUFGABBI-UHFFFAOYSA-N 4-(3-hydroxypropyl)isoindole-1,3-dione Chemical compound OCCCC1=CC=CC2=C1C(=O)NC2=O KHXUWBTUFGABBI-UHFFFAOYSA-N 0.000 description 3
BGJNRQSGJHVURK-UHFFFAOYSA-N 5-chloroisoindole-1,3-dione Chemical compound ClC1=CC=C2C(=O)NC(=O)C2=C1 BGJNRQSGJHVURK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
WRMUTKKSAKFVCP-UHFFFAOYSA-N 2-cyclohexyl-4-nitroisoindole-1,3-dione Chemical compound O=C1C=2C([N+](=O)[O-])=CC=CC=2C(=O)N1C1CCCCC1 WRMUTKKSAKFVCP-UHFFFAOYSA-N 0.000 description 2
XUIJACXTIJMYGJ-UHFFFAOYSA-N 2-cyclohexylisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCCCC1 XUIJACXTIJMYGJ-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001715 carbamic acids Chemical class 0.000 description 2
150000004653 carbonic acids Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
125000005543 phthalimide group Chemical class 0.000 description 2
150000003242 quaternary ammonium salts Chemical class 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
125000001302 tertiary amino group Chemical group 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
LDEUDIBESZBEQY-UHFFFAOYSA-N 2-(4-methylcyclohexyl)isoindole-1,3-dione Chemical compound C1CC(C)CCC1N1C(=O)C2=CC=CC=C2C1=O LDEUDIBESZBEQY-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 description 1
MHHGQWMCVNQHLG-UHFFFAOYSA-N 2-prop-2-enylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CC=C)C(=O)C2=C1 MHHGQWMCVNQHLG-UHFFFAOYSA-N 0.000 description 1
UQBKNSVYUASPMH-UHFFFAOYSA-N 4-chloro-2-cyclohexylisoindole-1,3-dione Chemical compound O=C1C=2C(Cl)=CC=CC=2C(=O)N1C1CCCCC1 UQBKNSVYUASPMH-UHFFFAOYSA-N 0.000 description 1
ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 description 1
CGFLAFZHQPHFEL-UHFFFAOYSA-N 5-chloro-2-(hydroxymethyl)isoindole-1,3-dione Chemical compound C1=C(Cl)C=C2C(=O)N(CO)C(=O)C2=C1 CGFLAFZHQPHFEL-UHFFFAOYSA-N 0.000 description 1
KVJYREOQXREEPT-UHFFFAOYSA-N 5-chloro-2-cyclohexylisoindole-1,3-dione Chemical compound O=C1C2=CC(Cl)=CC=C2C(=O)N1C1CCCCC1 KVJYREOQXREEPT-UHFFFAOYSA-N 0.000 description 1
DVDRUQOUGHIYCB-UHFFFAOYSA-N 5-fluoroisoindole-1,3-dione Chemical compound FC1=CC=C2C(=O)NC(=O)C2=C1 DVDRUQOUGHIYCB-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
QYWZYTTXGZLUPE-UHFFFAOYSA-N ClC=1C=C2C(C(=O)N(C2=O)CC#C)=CC=1 Chemical compound ClC=1C=C2C(C(=O)N(C2=O)CC#C)=CC=1 QYWZYTTXGZLUPE-UHFFFAOYSA-N 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
NRQWLDKACLGHPM-UHFFFAOYSA-N ICCC1=C2C(C(=O)NC2=O)=CC=C1 Chemical compound ICCC1=C2C(C(=O)NC2=O)=CC=C1 NRQWLDKACLGHPM-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
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
AMHXQVUODFNFGR-UHFFFAOYSA-K [Ag+3].[O-]P([O-])([O-])=O Chemical compound [Ag+3].[O-]P([O-])([O-])=O AMHXQVUODFNFGR-UHFFFAOYSA-K 0.000 description 1
WSNZLQGGHKYFAZ-UHFFFAOYSA-M [Na+].[O-]S(Cl)(=O)=O Chemical compound [Na+].[O-]S(Cl)(=O)=O WSNZLQGGHKYFAZ-UHFFFAOYSA-M 0.000 description 1
GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000011162 ammonium carbonates Nutrition 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical class NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 1
BUZRUIZTMOKRPB-UHFFFAOYSA-N carboxycarbamic acid Chemical class OC(=O)NC(O)=O BUZRUIZTMOKRPB-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-M chlorosulfate Chemical compound [O-]S(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-M 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
229940045803 cuprous chloride Drugs 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical class OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-L ethanedisulfonate group Chemical class C(CS(=O)(=O)[O-])S(=O)(=O)[O-] AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 description 1
150000002169 ethanolamines Chemical class 0.000 description 1
RAHHITDKGXOSCO-UHFFFAOYSA-N ethene;hydrochloride Chemical compound Cl.C=C RAHHITDKGXOSCO-UHFFFAOYSA-N 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
235000013905 glycine and its sodium salt Nutrition 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
KZQSXALQTHVPDQ-UHFFFAOYSA-M sodium;butanedioate;hydron Chemical compound [Na+].OC(=O)CCC([O-])=O KZQSXALQTHVPDQ-UHFFFAOYSA-M 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003566 thiocarboxylic acids Chemical class 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- 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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Indole Compounds (AREA)

CH399263A 1962-04-06 1963-03-29 Procédé de préparation de nouveaux composés hétérocycliques CH427800A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB1338962A GB1012235A (en)	1962-04-06	1962-04-06	Phthalimide derivatives
GB796863		1963-02-27

Publications (1)

Publication Number	Publication Date
CH427800A true CH427800A (fr)	1967-01-15

Family

ID=26241785

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH399263A CH427800A (fr)	1962-04-06	1963-03-29	Procédé de préparation de nouveaux composés hétérocycliques

Country Status (4)

Country	Link
AT (1)	AT242131B (da)
CH (1)	CH427800A (da)
DK (4)	DK105026C (da)
ES (1)	ES286793A1 (da)

1963
- 1963-03-29 CH CH399263A patent/CH427800A/fr unknown
- 1963-04-05 DK DK533864A patent/DK105026C/da active
- 1963-04-05 DK DK533664A patent/DK104789C/da active
- 1963-04-05 AT AT278863A patent/AT242131B/de active
- 1963-04-05 DK DK159863A patent/DK104846C/da active
- 1963-04-05 ES ES286793A patent/ES286793A1/es not_active Expired
- 1963-04-05 DK DK533764A patent/DK104739C/da active

Also Published As

Publication number	Publication date
DK104739C (da)	1966-06-27
AT242131B (de)	1965-08-25
DK104846C (da)	1966-07-11
ES286793A1 (es)	1963-11-16
DK105026C (da)	1966-08-08
DK104789C (da)	1966-07-04

Publication	Publication Date	Title
EP0522915B1 (fr)	1996-03-13	Dérivés de pyrimidine-4-carboxamide, leur préparation et leur application en thérapeutique
EP0002978B1 (fr)	1982-10-06	Dérivés de thiazolidinedione-2,4, leur préparation et leur application en thérapeutique
EP0965588B1 (fr)	2004-03-10	Procédé de préparation de dérivés de la 4-phényl-1,2,3,6-tétrahydropyridine et les produits intermédiaires mis en oeuvre
EP0086678A1 (fr)	1983-08-24	Procédé pour la préparation d'acyl-2 hexahydro-1,3,4,6,7,11b-2H-pyrazino (2,1-a)isoquinoléinones-4 et intermédiaires
BE779775A (fr)	1972-08-24	Derives de l'uree, procede pour les preparer et leurs applications
CH427800A (fr)	1967-01-15	Procédé de préparation de nouveaux composés hétérocycliques
EP0354093A1 (fr)	1990-02-07	Dérivés de pipérazine et leur procédé de préparation
FR2628738A1 (fr)	1989-09-22	Produits chimiques intermediaires utilisables pour la preparation de certains agents anti-histaminiques h2
BE858864A (fr)	1978-01-16	Nouveaux esters d'acides phenyl- et pyridine-3-carboxylique et procede permettant leur preparation
JP2000503993A (ja)	2000-04-04	Ｎ―（３―アミノ―４―クロロフェニル）アシルアミドの製造方法
CH620678A5 (en)	1980-12-15	Process for the preparation of a derivative of piperidine
EP0350384A1 (fr)	1990-01-10	Dérivés de sulfonyl indolizine, leur procédé de préparation et leur utilisation comme intermédiaires de synthèse
EP0929525A2 (fr)	1999-07-21	Nouvelles heteroaryloxyethylamines, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les contenant
FR2790472A1 (fr)	2000-09-08	Derives de cyclobutene-3, 4-dione, leur preparation et leur application en therapeutique
CA1086737A (fr)	1980-09-30	Derives de la thiazolo 3,4-b isoquinoleine, leur preparation et les compositions qui les contiennent
CH373038A (fr)	1963-11-15	Procédé de préparation de nouveaux éthers de pipéridyl-2 aryl méthanols
MC965A1 (fr)	1974-02-01	Nouvelle methode de préparation de 2-alcoxy-4,5-substitues benzamides
FR2489824A1 (fr)	1982-03-12	Procede pour la preparation d'esters d'acide apovincaminique et produits ainsi obtenus
FR2670208A1 (fr)	1992-06-12	Derives de phenyl-1 dihydro 1-4 arylalcoylamino-3 oxo-4 pyridazines, leur preparation et leur application en therapeutique.
FR2552086A1 (fr)	1985-03-22	Procede pour la preparation de derives condenses d'as-triazine, produits resultants et compositions pharmaceutiques les contenant
CH389642A (fr)	1965-03-31	Procédé de préparation de nouveaux dérivés du 3, 3 bis-(p-aminophényl)-butanone-(2)
BE630571A (da)
CH485663A (fr)	1970-02-15	Procédé de préparation de nouveaux dérivés benzéniques
CH527825A (fr)	1972-09-15	Procédé de fabrication de composés présentant une action thérapeutique
CH345015A (fr)	1960-03-15	Procédé de préparation de nouvelles amides