CH513868A - Verfahren zur Herstellung neuer Indenopyridinderivate - Google Patents

Verfahren zur Herstellung neuer Indenopyridinderivate

Info

Publication number: CH513868A
Authority: CH; Switzerland
Prior art keywords: 4ars; lower alkyl; 9brs; formula; 9bsr
Prior art date: 1969-04-08

Application number

CH240071A

Other languages

German (de)

English (en)

Inventor

Anton Dr Ebnoether

Jean-Michel Dr Bastian

Fulvio Dr Gadient

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.)

1969-04-08

Filing date

1969-04-08

Publication date

1971-10-15

1969-04-08 Application filed by Sandoz Ag filed Critical Sandoz Ag

1969-04-08 Priority to CH240071A priority Critical patent/CH513868A/de

1971-10-15 Publication of CH513868A publication Critical patent/CH513868A/de

Links

150000001875 compounds Chemical class 0.000 title claims description 28
239000002260 anti-inflammatory agent Substances 0.000 title 1
230000001741 anti-phlogistic effect Effects 0.000 title 1
125000000623 heterocyclic group Chemical group 0.000 title 1
239000000203 mixture Substances 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
229920000137 polyphosphoric acid Polymers 0.000 claims abstract description 6
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 11
229910052740 iodine Inorganic materials 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
239000011737 fluorine Chemical group 0.000 claims description 2
239000002253 acid Substances 0.000 abstract description 5
239000012280 lithium aluminium hydride Substances 0.000 abstract description 2
238000002360 preparation method Methods 0.000 abstract description 2
125000003545 alkoxy group Chemical group 0.000 abstract 2
125000000304 alkynyl group Chemical group 0.000 abstract 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 1
229910000091 aluminium hydride Inorganic materials 0.000 abstract 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
238000010438 heat treatment Methods 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
102220007331 rs111033633 Human genes 0.000 abstract 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000002904 solvent Substances 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
235000011121 sodium hydroxide Nutrition 0.000 description 12
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
239000012074 organic phase Substances 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
238000001816 cooling Methods 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
-1 Lithium aluminum hydride Chemical compound 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
239000002585 base Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
PFWJFKBTIBAASX-UHFFFAOYSA-N 9h-indeno[2,1-b]pyridine Chemical class C1=CN=C2CC3=CC=CC=C3C2=C1 PFWJFKBTIBAASX-UHFFFAOYSA-N 0.000 description 2
KDLHGLXUTDYEIU-UHFFFAOYSA-N ClC1=CC=C(C(=O)C2C(CN(CC2)C)C2=CC=C(C=C2)Cl)C=C1 Chemical compound ClC1=CC=C(C(=O)C2C(CN(CC2)C)C2=CC=C(C=C2)Cl)C=C1 KDLHGLXUTDYEIU-UHFFFAOYSA-N 0.000 description 2
XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
229940077388 benzenesulfonate Drugs 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
GKMQAGZRPQBLHG-UHFFFAOYSA-N ethyl 1-methyl-3,6-dihydro-2h-pyridine-4-carboxylate Chemical compound CCOC(=O)C1=CCN(C)CC1 GKMQAGZRPQBLHG-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000012730 sustained-release form Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 1
ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
CNTZJXJNWIQXHW-UHFFFAOYSA-N CN(CCC1CC(C=CC(Cl)=C2)=C2O)CC1C(C=C1)=CC=C1Cl Chemical compound CN(CCC1CC(C=CC(Cl)=C2)=C2O)CC1C(C=C1)=CC=C1Cl CNTZJXJNWIQXHW-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 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
206010040108 Serotonin syndrome Diseases 0.000 description 1
YHLKUNQGPQLAIB-UHFFFAOYSA-N [1-methyl-3-(4-methylphenyl)piperidin-4-yl]-(4-methylphenyl)methanone Chemical compound CN1CC(C(CC1)C(=O)C1=CC=C(C=C1)C)C1=CC=C(C=C1)C YHLKUNQGPQLAIB-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
239000008280 blood Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000012937 correction Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000001035 drying Methods 0.000 description 1
229940064982 ethylnicotinate Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000002401 inhibitory effect Effects 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
239000012452 mother liquor Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Hydrogenated Pyridines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

CH240071A 1969-04-08 1969-04-08 Verfahren zur Herstellung neuer Indenopyridinderivate CH513868A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH240071A CH513868A (de)	1969-04-08	1969-04-08	Verfahren zur Herstellung neuer Indenopyridinderivate

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH525869A CH513864A (de)	1969-04-08	1969-04-08	Verfahren zur Herstellung neuer Indenopyridinderivate
CH240071A CH513868A (de)	1969-04-08	1969-04-08	Verfahren zur Herstellung neuer Indenopyridinderivate

Publications (1)

Publication Number	Publication Date
CH513868A true CH513868A (de)	1971-10-15

Family

ID=4290579

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
CH240071A CH513868A (de)	1969-04-08	1969-04-08	Verfahren zur Herstellung neuer Indenopyridinderivate
CH525869A CH513864A (de)	1969-04-08	1969-04-08	Verfahren zur Herstellung neuer Indenopyridinderivate
CH240171A CH513869A (de)	1969-04-08	1969-04-08	Verfahren zur Herstellung neuer Indenopyridinderivate
CH239971A CH513867A (de)	1969-04-08	1969-04-08	Verfahren zur Herstellung neuer Indenopyridinderivate

Family Applications After (3)

Application Number	Title	Priority Date	Filing Date
CH525869A CH513864A (de)	1969-04-08	1969-04-08	Verfahren zur Herstellung neuer Indenopyridinderivate
CH240171A CH513869A (de)	1969-04-08	1969-04-08	Verfahren zur Herstellung neuer Indenopyridinderivate
CH239971A CH513867A (de)	1969-04-08	1969-04-08	Verfahren zur Herstellung neuer Indenopyridinderivate

Country Status (6)

Country	Link
AT (2)	AT312609B (cs)
CH (4)	CH513868A (cs)
CS (2)	CS162709B2 (cs)
RO (3)	RO59004A (cs)
SU (3)	SU386513A3 (cs)
ZA (1)	ZA702320B (cs)

1969
- 1969-04-08 CH CH240071A patent/CH513868A/de not_active IP Right Cessation
- 1969-04-08 CH CH525869A patent/CH513864A/de not_active IP Right Cessation
- 1969-04-08 CH CH240171A patent/CH513869A/de not_active IP Right Cessation
- 1969-04-08 CH CH239971A patent/CH513867A/de not_active IP Right Cessation
1970
- 1970-04-07 SU SU1425236A patent/SU386513A3/ru active
- 1970-04-07 RO RO70273A patent/RO59004A/ro unknown
- 1970-04-07 AT AT267772A patent/AT312609B/de not_active IP Right Cessation
- 1970-04-07 RO RO70274A patent/RO59005A/ro unknown
- 1970-04-07 CS CS2307A patent/CS162709B2/cs unknown
- 1970-04-07 CS CS735709A patent/CS162712B2/cs unknown
- 1970-04-07 SU SU1705760A patent/SU422147A3/ru active
- 1970-04-07 RO RO70275A patent/RO58957A/ro unknown
- 1970-04-07 AT AT316470A patent/AT312605B/de not_active IP Right Cessation
- 1970-04-07 SU SU1697745A patent/SU415873A3/ru active
- 1970-04-08 ZA ZA702320A patent/ZA702320B/xx unknown

Also Published As

Publication number	Publication date
CS162712B2 (en)	1975-07-15
ZA702320B (en)	1971-11-24
RO59004A (cs)	1976-02-15
CS162709B2 (cs)	1975-07-15
SU422147A3 (ru)	1974-03-30
CH513869A (de)	1971-10-15
SU386513A3 (cs)	1973-06-14
SU415873A3 (cs)	1974-02-15
AT312605B (de)	1974-01-10
RO59005A (cs)	1976-04-15
AT312609B (de)	1974-01-10
CH513864A (de)	1971-10-15
RO58957A (cs)	1975-11-15
CH513867A (de)	1971-10-15

Legal Events

Date	Code	Title	Description
1981-12-31	PL	Patent ceased

Publication	Publication Date	Title
DE2733868C2 (de)	1987-05-14	Neue 1,2,4,5-Tetrahydro-3H-2-benzazepin-3-one, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
CH620439A5 (en)	1980-11-28	Process for the preparation of 2-tetrahydrofurfuryl- 6,7-benzomorphans
DE2851028A1 (de)	1979-05-31	Neue indolo eckige klammer auf 2.3-a eckige klammer zu chinolizidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitung
CH500194A (de)	1970-12-15	Verfahren zur Herstellung von Tetrahydroazepinderivaten
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