CH513869A - Verfahren zur Herstellung neuer Indenopyridinderivate - Google Patents

Verfahren zur Herstellung neuer Indenopyridinderivate

Info

Publication number: CH513869A
Authority: CH; Switzerland
Prior art keywords: formula; 4ars; lower alkyl; 9brs; compounds
Prior art date: 1969-04-08

Application number

CH240171A

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 CH240171A priority Critical patent/CH513869A/de

1971-10-15 Publication of CH513869A publication Critical patent/CH513869A/de

Links

150000001875 compounds Chemical class 0.000 title claims description 46
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
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
239000000203 mixture Substances 0.000 claims abstract description 16
238000002360 preparation method Methods 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
229910052794 bromium Inorganic materials 0.000 claims abstract description 7
229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
239000012280 lithium aluminium hydride Substances 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 15
-1 lithium aluminum hydride Chemical compound 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
239000011737 fluorine Chemical group 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
QBMTZNAOBBVWIE-UHFFFAOYSA-N 5-phenyl-2,3,4,4a,5,9b-hexahydro-1H-indeno[1,2-c]pyridine Chemical class C1(=CC=CC=C1)C1C2=CC=CC=C2C2CNCCC21 QBMTZNAOBBVWIE-UHFFFAOYSA-N 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
239000002253 acid Substances 0.000 abstract description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 3
229920000137 polyphosphoric acid Polymers 0.000 abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
125000003342 alkenyl group Chemical group 0.000 abstract 3
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
150000002148 esters Chemical class 0.000 abstract 1
238000010438 heat treatment Methods 0.000 abstract 1
102220007331 rs111033633 Human genes 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
CYNOIDSFCNRVHZ-UHFFFAOYSA-N 7-chloro-5-(4-chlorophenyl)-2-methyl-1,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridine Chemical compound C1N(C)CCC2C1C1=CC=C(Cl)C=C1C2C1=CC=C(Cl)C=C1 CYNOIDSFCNRVHZ-UHFFFAOYSA-N 0.000 description 2
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
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
241000124008 Mammalia Species 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
150000002902 organometallic compounds Chemical class 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
239000007787 solid Substances 0.000 description 2
125000001424 substituent group Chemical group 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
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
SVCFFBMBIBMUQQ-UHFFFAOYSA-N 2h-indeno[1,2-c]pyridine Chemical compound N1C=CC2=CC3=CC=CC=C3C2=C1 SVCFFBMBIBMUQQ-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
TYYJGUOCMAQCHR-UHFFFAOYSA-N CCOC(C1=C2C3=CC=CC=C3C=C2C=CN1)=O Chemical compound CCOC(C1=C2C3=CC=CC=C3C=C2C=CN1)=O TYYJGUOCMAQCHR-UHFFFAOYSA-N 0.000 description 1
VKXFGYWOQVRKMC-UHFFFAOYSA-N CN1CCC(C(O)C2=CC=C(Cl)C=C2)C(C1)C1=CC=C(Cl)C=C1 Chemical compound CN1CCC(C(O)C2=CC=C(Cl)C=C2)C(C1)C1=CC=C(Cl)C=C1 VKXFGYWOQVRKMC-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000700198 Cavia Species 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
206010040108 Serotonin syndrome Diseases 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000005431 alkyl carboxamide group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 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
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-aminopropionic acid Natural products NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
230000000911 decarboxylating effect Effects 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
FQYYIPZPELSLDK-UHFFFAOYSA-N ethyl pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC=N1 FQYYIPZPELSLDK-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
YNXURHRFIMQACJ-UHFFFAOYSA-N lithium;methanidylbenzene Chemical compound [Li+].[CH2-]C1=CC=CC=C1 YNXURHRFIMQACJ-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
QGEFGPVWRJCFQP-UHFFFAOYSA-M magnesium;methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC=C1 QGEFGPVWRJCFQP-UHFFFAOYSA-M 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 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
150000003673 urethanes Chemical class 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)

CH240171A 1969-04-08 1969-04-08 Verfahren zur Herstellung neuer Indenopyridinderivate CH513869A (de)

Priority Applications (1)

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

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH240171A CH513869A (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

Publications (1)

Publication Number	Publication Date
CH513869A true CH513869A (de)	1971-10-15

Family

ID=4290579

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
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
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

Family Applications After (3)

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

Country Status (6)

Country	Link
AT (2)	AT312609B (cs)
CH (4)	CH513869A (cs)
CS (2)	CS162709B2 (cs)
RO (3)	RO58957A (cs)
SU (3)	SU422147A3 (cs)
ZA (1)	ZA702320B (cs)

1969
- 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
- 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
1970
- 1970-04-07 CS CS2307A patent/CS162709B2/cs unknown
- 1970-04-07 RO RO70275A patent/RO58957A/ro unknown
- 1970-04-07 SU SU1705760A patent/SU422147A3/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 CS CS735709A patent/CS162712B2/cs unknown
- 1970-04-07 RO RO70274A patent/RO59005A/ro unknown
- 1970-04-07 SU SU1697745A patent/SU415873A3/ru active
- 1970-04-07 SU SU1425236A patent/SU386513A3/ru active
- 1970-04-07 AT AT316470A patent/AT312605B/de not_active IP Right Cessation
- 1970-04-08 ZA ZA702320A patent/ZA702320B/xx unknown

Also Published As

Publication number	Publication date
CH513867A (de)	1971-10-15
SU386513A3 (cs)	1973-06-14
SU415873A3 (cs)	1974-02-15
CS162712B2 (en)	1975-07-15
RO59004A (cs)	1976-02-15
RO58957A (cs)	1975-11-15
RO59005A (cs)	1976-04-15
SU422147A3 (ru)	1974-03-30
ZA702320B (en)	1971-11-24
CS162709B2 (cs)	1975-07-15
AT312605B (de)	1974-01-10
CH513868A (de)	1971-10-15
AT312609B (de)	1974-01-10
CH513864A (de)	1971-10-15

Legal Events

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

Publication	Publication Date	Title
CH513869A (de)	1971-10-15	Verfahren zur Herstellung neuer Indenopyridinderivate
CH556837A (de)	1974-12-13	Verfahren zur herstellung neuer spiroindanpyrrolidinderivate.
CH630903A5 (en)	1982-07-15	Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline.
DE2526966A1 (de)	1976-01-08	Tricyclische alkylaminverbindungen, verfahren zu ihrer herstellung und sie enthaltende mittel
AT323163B (de)	1975-06-25	Verfahren zur herstellung neuer (4ars,5sr,9bsr)- und (4ars,5sr,9brs)-1,3,4,4a,5,9b-hexahydro-5-phenyl-2h-indeno(1,2-c)pyridine und ihrer saureadditionssalze
AT312608B (de)	1974-01-10	Verfahren zur Herstellung neuer (4aRS,5SR,9bSR)- und (4aRS,5SR,9bRS)-1,3,4,4a,5,9b-Hexahydro-5-phenyl-2H-indeno[1,2-c]pyridine und ihrer Säureadditionssalze
EP0001585B1 (de)	1981-07-22	Piperazino-pyrrolobenzodiazepine, Verfahren zu ihrer Herstellung sowie pharmazeutische Präparate enthaltend diese Verbindungen
DE2016268C3 (de)	1980-10-09	(4aRS, 5SR, 9bSR)- und (4aRS, 5SR, 9bRS) -13,4,4a3,9b-Hexahydro-5-phenyl2H-indeno [Uc] pyridine, ihre Salze, Verfahren zu ihrer Herstellung und Arzneimittel
CH517744A (de)	1972-01-15	Verfahren zur Herstellung neuer Indenopyridinderivate
CH535767A (de)	1973-04-15	Verfahren zur Herstellung neuer N-Phenäthylpiperidinderivate
AT367404B (de)	1982-07-12	Verfahren zur herstellung von neuen 1,2,3,4,4a, 10b-hexahydro-benz(f)isochinolinderivaten und ihren saeureadditionssalzen
CH618673A5 (cs)	1980-08-15
US3551449A (en)	1970-12-29	Bis(alkoxyphenyl)pyrroles and pyrrolines
AT367406B (de)	1982-07-12	Verfahren zur herstellung von neuen 1,2,3,4,4a, 10b-hexahydro-benz(f)isochinolinderivaten und ihren saeureadditionssalzen
CH513165A (de)	1971-09-30	Verfahren zur Herstellung neuer 1,3,4,9b-Tetrahydro-2H-indeno(1,2-c)pyridinderivate
AT367420B (de)	1982-07-12	Verfahren zur herstellung neuer vincaminderivate
AT330181B (de)	1976-06-25	Verfahren zur herstellung von neuen chinolinessigsaurederivaten und ihren salzen
CH513865A (de)	1971-10-15	Verfahren zur Herstellung neuer Indenopyridinderivate
CH532014A (de)	1972-12-31	Verfahren zur Herstellung neuer, in Stellung 5 substituierter 5H-Dibenzo(a,d)cycloheptene
CH494237A (de)	1970-07-31	Verfahren zur Herstellung neuer Benzothiopyranopyridinderivate
CH528507A (de)	1972-09-30	Verfahren zur Herstellung neuer 1-Phenäthylpiperidin-Derivate
DE1470065B2 (de)	1979-11-08	Verfahren zur Herstellung von Chinolizinderivaten
CH596207A5 (en)	1978-03-15	Vincamine derivs for treating behaviour disorders
CH612906A5 (en)	1979-08-31	Process for the preparation of 10-(2'-dialkylaminoethyl)-10,11-dihydro-5-methylene-5H-dibenzo[a,d]cyc loheptene
CH513872A (de)	1971-10-15	Verfahren zur Herstellung von neuen anellierten oder überbrückten N'-monosubstituierten N-Acylpyrazolidinen