CH497454A - Verfahren zur Herstellung von 1',2',4',5'-Tetrahydrospiro (1,3-benzodioxol-2,3'-pyrrol) - Google Patents

Verfahren zur Herstellung von 1',2',4',5'-Tetrahydrospiro (1,3-benzodioxol-2,3'-pyrrol)

Info

Publication number: CH497454A
Authority: CH; Switzerland
Prior art keywords: cpds; carbocyclic; trans; iii; nickel
Prior art date: 1968-01-24

Application number

CH111868A

Other languages

German (de)

English (en)

Inventor

John Dr Gmuender

Richard Dr Berthold

Original Assignee

Sandoz Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1968-01-24

Filing date

1968-01-24

Publication date

1970-10-15

1968-01-24 Application filed by Sandoz Ag filed Critical Sandoz Ag

1968-01-24 Priority to CH111868A priority Critical patent/CH497454A/de

1968-12-31 Priority to NL6818875A priority patent/NL6818875A/xx

1969-01-03 Priority to SE00061/69A priority patent/SE349586B/xx

1969-01-08 Priority to GB0136/69A priority patent/GB1241512A/en

1969-01-15 Priority to US791509*A priority patent/US3560522A/en

1969-01-22 Priority to DE1903035A priority patent/DE1903035C3/de

1969-01-22 Priority to AT65169A priority patent/AT299182B/de

1969-01-22 Priority to ES362794A priority patent/ES362794A1/es

1969-01-23 Priority to BE727330D priority patent/BE727330A/xx

1969-01-23 Priority to FR6901206A priority patent/FR2000649A1/fr

1969-01-23 Priority to PL13134069A priority patent/PL72589B1/pl

1970-10-15 Publication of CH497454A publication Critical patent/CH497454A/de

Links

KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title abstract 6
239000004215 Carbon black (E152) Substances 0.000 title abstract 3
125000002837 carbocyclic group Chemical group 0.000 title abstract 3
239000003446 ligand Substances 0.000 title abstract 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 3
238000003776 cleavage reaction Methods 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
230000007017 scission Effects 0.000 claims 1
OUJKSHSWNVQPCI-UHFFFAOYSA-N spiro[1,3-benzodioxole-2,3'-pyrrolidine] Chemical compound C1NCCC21OC1=CC=CC=C1O2 OUJKSHSWNVQPCI-UHFFFAOYSA-N 0.000 claims 1
-1 halogenated nickel hydrocarbon Chemical class 0.000 abstract description 4
238000006243 chemical reaction Methods 0.000 abstract 3
150000004696 coordination complex Chemical class 0.000 abstract 2
IJFJCLHXDDMMIY-WGSXVXHRSA-N (1E)-12-ethenylcyclotetradeca-1,5,9-triene Chemical compound C(=C)C1CC=CCCC=CCC/C=C/CC1 IJFJCLHXDDMMIY-WGSXVXHRSA-N 0.000 abstract 1
KEQDWEYHMVRPTJ-WOJBTPEYSA-N (1E)-16-ethenylcyclooctadeca-1,5,9,13-tetraene Chemical compound C(=C)C1CC=CCCC=CCCC=CCC/C=C/CC1 KEQDWEYHMVRPTJ-WOJBTPEYSA-N 0.000 abstract 1
HSXHQSIOZSTGKP-UHFFFAOYSA-N C/1=CCCC=CCCC=CCCC=CCC1 Chemical compound C/1=CCCC=CCCC=CCCC=CCC1 HSXHQSIOZSTGKP-UHFFFAOYSA-N 0.000 abstract 1
NBIGCYKXEHDWSI-UHFFFAOYSA-N cycloicosa-1,5,9,13,17-pentaene Chemical compound C1CC=CCCC=CCCC=CCCC=CCCC=C1 NBIGCYKXEHDWSI-UHFFFAOYSA-N 0.000 abstract 1
239000000539 dimer Substances 0.000 abstract 1
229930195733 hydrocarbon Natural products 0.000 abstract 1
239000013638 trimer Substances 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000001430 anti-depressive effect Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
CLUKSDXRKWQPCV-UHFFFAOYSA-N 2-[2-(methylsulfonyloxymethyl)-1,3-benzodioxol-2-yl]ethyl methanesulfonate Chemical compound CS(=O)(=O)OCCC1(OC2=C(O1)C=CC=C2)COS(=O)(=O)C CLUKSDXRKWQPCV-UHFFFAOYSA-N 0.000 description 2
208000020401 Depressive disease Diseases 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
239000000935 antidepressant agent Substances 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
DXRRTRDMFZNALM-UHFFFAOYSA-N ethyl 2-(2-ethoxy-2-oxoethyl)-1,3-benzodioxole-2-carboxylate Chemical compound CCOC(=O)CC1(OC2=C(O1)C=CC=C2)C(=O)OCC DXRRTRDMFZNALM-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
150000003413 spiro compounds Chemical class 0.000 description 2
239000000725 suspension Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
YZBPMZSIOPOYHY-UHFFFAOYSA-N 1'-benzylspiro[1,3-benzodioxole-2,3'-pyrrolidine] Chemical compound C(C1=CC=CC=C1)N1CC2(OC3=C(O2)C=CC=C3)CC1 YZBPMZSIOPOYHY-UHFFFAOYSA-N 0.000 description 1
FJWGRXKOBIVTFA-UHFFFAOYSA-N 2,3-dibromobutanedioic acid Chemical compound OC(=O)C(Br)C(Br)C(O)=O FJWGRXKOBIVTFA-UHFFFAOYSA-N 0.000 description 1
ZZIANOWSAVHIBY-UHFFFAOYSA-N 2-[2-(hydroxymethyl)-1,3-benzodioxol-2-yl]ethanol Chemical compound OCCC1(OC2=C(O1)C=CC=C2)CO ZZIANOWSAVHIBY-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
208000009132 Catalepsy Diseases 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
206010015995 Eyelid ptosis Diseases 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
WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
206010047853 Waxy flexibility Diseases 0.000 description 1
208000012826 adjustment disease Diseases 0.000 description 1
230000001078 anti-cholinergic effect Effects 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical class CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000012937 correction Methods 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
MHUWZNTUIIFHAS-CLFAGFIQSA-N dioleoyl phosphatidic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC MHUWZNTUIIFHAS-CLFAGFIQSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000002651 drug therapy Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
230000005284 excitation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229960004502 levodopa Drugs 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
229960005333 tetrabenazine Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH111868A 1968-01-24 1968-01-24 Verfahren zur Herstellung von 1',2',4',5'-Tetrahydrospiro (1,3-benzodioxol-2,3'-pyrrol) CH497454A (de)

Priority Applications (11)

Application Number	Priority Date	Filing Date	Title
CH111868A CH497454A (de)	1968-01-24	1968-01-24	Verfahren zur Herstellung von 1',2',4',5'-Tetrahydrospiro (1,3-benzodioxol-2,3'-pyrrol)
NL6818875A NL6818875A (pl)	1968-01-24	1968-12-31
SE00061/69A SE349586B (pl)	1968-01-24	1969-01-03
GB0136/69A GB1241512A (en)	1968-01-24	1969-01-08	Novel spiro-heterocyclic compound
US791509*A US3560522A (en)	1968-01-24	1969-01-15	Spiro(1,3-benzodioxol-2,3'-pyrrolidine) and intermediates therefor
DE1903035A DE1903035C3 (de)	1968-01-24	1969-01-22	Spiro(1,3-benzodioxol-2,3'-pyrrolidln) und seine Säureadditionssalze
AT65169A AT299182B (de)	1968-01-24	1969-01-22	Verfahren zur Herstellung des neuen Spiro[1,3-benzodioxol-2,3'-pyrrolidins] und seiner Salze
ES362794A ES362794A1 (es)	1968-01-24	1969-01-22	Procedimiento para la obtencion de espiro (1,3)-benzodioxol-2,3-pirrolidina.
BE727330D BE727330A (pl)	1968-01-24	1969-01-23
FR6901206A FR2000649A1 (pl)	1968-01-24	1969-01-23
PL13134069A PL72589B1 (pl)	1968-01-24	1969-01-23

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH111868A CH497454A (de)	1968-01-24	1968-01-24	Verfahren zur Herstellung von 1',2',4',5'-Tetrahydrospiro (1,3-benzodioxol-2,3'-pyrrol)

Publications (1)

Publication Number	Publication Date
CH497454A true CH497454A (de)	1970-10-15

Family

ID=4202906

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH111868A CH497454A (de)	1968-01-24	1968-01-24	Verfahren zur Herstellung von 1',2',4',5'-Tetrahydrospiro (1,3-benzodioxol-2,3'-pyrrol)

Country Status (3)

Country	Link
AT (1)	AT299182B (pl)
CH (1)	CH497454A (pl)
PL (1)	PL72589B1 (pl)

1968
- 1968-01-24 CH CH111868A patent/CH497454A/de not_active IP Right Cessation
1969
- 1969-01-22 AT AT65169A patent/AT299182B/de active
- 1969-01-23 PL PL13134069A patent/PL72589B1/pl unknown

Also Published As

Publication number	Publication date
AT299182B (de)	1972-06-12
PL72589B1 (pl)	1974-08-30

Legal Events

Date	Code	Title	Description
1976-08-31	PL	Patent ceased

Publication	Publication Date	Title
DE2807623A1 (de)	1978-08-31	Pyrrolidinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
CH497454A (de)	1970-10-15	Verfahren zur Herstellung von 1',2',4',5'-Tetrahydrospiro (1,3-benzodioxol-2,3'-pyrrol)
CH616142A5 (pl)	1980-03-14
CH636076A5 (de)	1983-05-13	Benzylalkoholderivate und verfahren zu deren herstellung.
DE2653477A1 (de)	1977-06-08	Spiro eckige klammer auf cyclopropan- 1,2'-indolin eckige klammer zu -3'-one
DE3020298C2 (de)	1983-04-28	Verfahren zur Herstellung von 2,2,4,5,5-Pentamethyl-3-formyl-3-pyrrolin
DE1903035C3 (de)	1975-02-20	Spiro(1,3-benzodioxol-2,3'-pyrrolidln) und seine Säureadditionssalze
AT208872B (de)	1960-05-10	Verfahren zur Herstellung neuer 1,4-Diazacycloheptane
DE1959562A1 (de)	1971-06-03	Neue Benzodioxanderivate
CH627169A5 (pl)	1981-12-31
AT318557B (de)	1974-10-25	Verfahren zur Herstellung von neuen 2-exo-Aminobornanen und von deren Säureadditionssalzen
AT265274B (de)	1968-10-10	Verfahren zur Herstellung von neuen 2-Oxo-7-phenyl-1,2,3,4,6,7-hexahydro-11bH-benzo[a]-chinolizinen sowie von deren Säureadditions- und quartären Ammoniumsalzen
AT202145B (de)	1959-02-10	Verfahren zur Herstellung von substituierten 2-Oxo-benzo-chinolizinen
AT343106B (de)	1978-05-10	Verfahren zur herstellung von neuen aminoalkylestern von indanylcarbonsauren
AT228211B (de)	1963-07-10	Verfahren zur Herstellung von neuen Phenothiazinderivaten, sowie von Säureadditionssalzen und quartären Salzen dieser Phenothiazinderivate
CH464924A (de)	1968-11-15	Verfahren zur Herstellung von neuen Pyrrolidinderivaten
AT219037B (de)	1962-01-10	Verfahren zur Herstellung neuer, basischer Indol-Derivate
DE1668208B2 (de)	1980-11-06	Tricyclische Amine, deren Salze, Verfahren zu deren Herstellung und diese enthaltende Mittel
AT213885B (de)	1961-03-10	Verfahren zur Herstellung von neuen Indol-Derivaten
AT269139B (de)	1969-03-10	Verfahren zur Herstellung neuer Piperidin-Derivate und ihrer Säureadditionssalze
AT361003B (de)	1981-02-10	Verfahren zur herstellung von neuen 2,9- -dioxatricyclo(4,3,1,03,7)decanen und deren salzen
AT372945B (de)	1983-11-25	Verfahren zur herstellung von neuen nsubstituierten moranolinderivaten
DE1595903C (de)	1972-10-05	1-Substituierte 2,6-Dimethyl-4-phenylpiperazine
CH617177A5 (pl)	1980-05-14
DE3721723A1 (de)	1989-01-12	Substituierte 6-oxo-decahydroisochinoline, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie bei der herstellung anfallenden neuen zwischenprodukte