CH516558A - Verfahren zur Herstellung neuer Indenopyridinderivate - Google Patents

Verfahren zur Herstellung neuer Indenopyridinderivate

Info

Publication number: CH516558A
Authority: CH; Switzerland
Prior art keywords: formula; acid; hydrogen; acid addition; alkyl
Prior art date: 1969-05-07

Application number

CH696769A

Other languages

German (de)

English (en)

Inventor

Anton Dr Ebnoether

Jean-Michel Dr Bastian

Erwin Dr Rissi

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.)

1969-05-07

Filing date

1969-05-07

Publication date

1971-12-15

1969-05-07 Application filed by Sandoz Ag filed Critical Sandoz Ag

1969-05-07 Priority to CH870171A priority Critical patent/CH520141A/de

1969-05-07 Priority to CH696769A priority patent/CH516558A/de

1969-05-07 Priority to CH870271A priority patent/CH520142A/de

1970-04-10 Priority to CY819A priority patent/CY819A/xx

1970-04-10 Priority to GB1708070A priority patent/GB1306404A/en

1970-04-29 Priority to NL7006274A priority patent/NL7006274A/xx

1970-04-30 Priority to US33498A priority patent/US3678058A/en

1970-05-04 Priority to FR7016162A priority patent/FR2051503B1/fr

1970-05-04 Priority to DE19702021747 priority patent/DE2021747A1/de

1970-05-05 Priority to PL1970140430A priority patent/PL80561B1/pl

1970-05-05 Priority to FI701261A priority patent/FI51478C/fi

1970-05-05 Priority to IE586/70A priority patent/IE35052B1/xx

1970-05-05 Priority to SU1839956A priority patent/SU517256A3/ru

1970-05-05 Priority to NO1707/70A priority patent/NO132478C/no

1970-05-05 Priority to CS3286A priority patent/CS164267B2/cs

1970-05-05 Priority to SU1435714A priority patent/SU383293A3/ru

1970-05-05 Priority to CS3110A priority patent/CS164266B2/cs

1970-05-05 Priority to IL34468A priority patent/IL34468A/en

1970-05-05 Priority to ES379299A priority patent/ES379299A1/es

1970-05-05 Priority to SE7006162A priority patent/SE375310B/xx

1970-05-05 Priority to BE749984D priority patent/BE749984A/fr

1970-05-06 Priority to CA081,987,A priority patent/CA951734A/en

1970-05-06 Priority to ZA703062A priority patent/ZA703062B/xx

1970-05-06 Priority to AT410570A priority patent/AT313898B/de

1971-12-15 Publication of CH516558A publication Critical patent/CH516558A/de

1972-12-01 Priority to ES409197A priority patent/ES409197A1/es

1972-12-01 Priority to ES409196A priority patent/ES409196A1/es

1975-12-30 Priority to MY239/75A priority patent/MY7500239A/xx

Links

239000003814 drug Substances 0.000 title description 3
239000002253 acid Substances 0.000 claims abstract description 36
150000003839 salts Chemical class 0.000 claims abstract description 21
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
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 3
150000001875 compounds Chemical class 0.000 claims description 38
238000000034 method Methods 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 5
PFWJFKBTIBAASX-UHFFFAOYSA-N 9h-indeno[2,1-b]pyridine Chemical class C1=CN=C2CC3=CC=CC=C3C2=C1 PFWJFKBTIBAASX-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims description 2
UINFICGYFFOSMB-UHFFFAOYSA-N propanoate;pyridin-1-ium Chemical compound CCC(O)=O.C1=CC=NC=C1 UINFICGYFFOSMB-UHFFFAOYSA-N 0.000 claims 1
-1 anti-ulcerous Substances 0.000 abstract description 4
150000004820 halides Chemical class 0.000 abstract description 3
230000000767 anti-ulcer Effects 0.000 abstract description 2
208000001953 Hypotension Diseases 0.000 abstract 1
229940124332 anorexigenic agent Drugs 0.000 abstract 1
239000002260 anti-inflammatory agent Substances 0.000 abstract 1
230000001741 anti-phlogistic effect Effects 0.000 abstract 1
239000002220 antihypertensive agent Substances 0.000 abstract 1
239000002830 appetite depressant Substances 0.000 abstract 1
208000021822 hypotensive Diseases 0.000 abstract 1
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
230000037396 body weight Effects 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000012730 sustained-release form Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
241000700159 Rattus Species 0.000 description 3
150000001649 bromium compounds Chemical class 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
150000004694 iodide salts Chemical class 0.000 description 3
239000000155 melt Substances 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
239000002585 base Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
150000002440 hydroxy compounds Chemical class 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
ZEVIVLCBODXZAW-UHFFFAOYSA-N 2,3,4,4a,5,9b-hexahydro-1h-indeno[1,2-c]pyridin-5-ol Chemical compound C12=CC=CC=C2C(O)C2C1CNCC2 ZEVIVLCBODXZAW-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
BQTJMKIHKULPCZ-UHFFFAOYSA-N 2H-indene Chemical compound C1=CC=CC2=CCC=C21 BQTJMKIHKULPCZ-UHFFFAOYSA-N 0.000 description 1
IYOIBZYIRXERTL-UHFFFAOYSA-N 3-pyridin-2-ylpropanamide Chemical compound NC(=O)CCC1=CC=CC=N1 IYOIBZYIRXERTL-UHFFFAOYSA-N 0.000 description 1
CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 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
206010030113 Oedema Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000005431 alkyl carboxamide group Chemical group 0.000 description 1
230000002891 anorexigenic effect Effects 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
235000012631 food intake Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
150000002681 magnesium compounds Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000012545 processing Methods 0.000 description 1
YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000004071 soot Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
231100000397 ulcer Toxicity 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

Landscapes

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

CH696769A 1969-05-07 1969-05-07 Verfahren zur Herstellung neuer Indenopyridinderivate CH516558A (de)

Priority Applications (27)

Application Number	Priority Date	Filing Date	Title
CH870171A CH520141A (de)	1969-05-07	1969-05-07	Verfahren zur Herstellung neuer Indenopyridinderivate
CH696769A CH516558A (de)	1969-05-07	1969-05-07	Verfahren zur Herstellung neuer Indenopyridinderivate
CH870271A CH520142A (de)	1969-05-07	1969-05-07	Verfahren zur Herstellung neuer Indenopyridinderivate
CY819A CY819A (en)	1969-05-07	1970-04-10	Indenopyridine derivatives
GB1708070A GB1306404A (en)	1969-05-07	1970-04-10	Indenopyridine derivatives
NL7006274A NL7006274A (cs)	1969-05-07	1970-04-29
US33498A US3678058A (en)	1969-05-07	1970-04-30	1,3,4,9B-TETRAHYDRO-2(2H)-INDENO-{8 1,2-c{9 PYRIDINES
FR7016162A FR2051503B1 (cs)	1969-05-07	1970-05-04
DE19702021747 DE2021747A1 (de)	1969-05-07	1970-05-04	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
NO1707/70A NO132478C (cs)	1969-05-07	1970-05-05
ES379299A ES379299A1 (es)	1969-05-07	1970-05-05	Procedimiento para la obtencion de derivados de indenopiri-dina.
IE586/70A IE35052B1 (en)	1969-05-07	1970-05-05	Indenopyridine derivatives
SU1839956A SU517256A3 (ru)	1969-05-07	1970-05-05	Способ получени кислотных солей инденопиридинов
PL1970140430A PL80561B1 (cs)	1969-05-07	1970-05-05
CS3286A CS164267B2 (cs)	1969-05-07	1970-05-05
SU1435714A SU383293A3 (cs)	1969-05-07	1970-05-05
CS3110A CS164266B2 (cs)	1969-05-07	1970-05-05
IL34468A IL34468A (en)	1969-05-07	1970-05-05	Acidic salt salts of the history of indonopyridine, their preparation and pharmaceutical preparations containing them
FI701261A FI51478C (fi)	1969-05-07	1970-05-05	Menetelmä terapeuttisesti vaikuttavien 1,3,4,9b-tetrahydro-2(2H)-inden o(1,2-c)pyridiinijohdannaisten happoadditiosuolojen valmistamiseksi.
SE7006162A SE375310B (cs)	1969-05-07	1970-05-05
BE749984D BE749984A (fr)	1969-05-07	1970-05-05	Nouveaux derives de l'indenopyridine, leur preparation et medicaments abase de ces derives
CA081,987,A CA951734A (en)	1969-05-07	1970-05-06	Indenopyridine derivatives
ZA703062A ZA703062B (en)	1969-05-07	1970-05-06	Improvements in or relating to organic compounds
AT410570A AT313898B (de)	1969-05-07	1970-05-06	Verfahren zur Herstellung von Säureadditionssalzen neuer Indenopyridinderivate
ES409197A ES409197A1 (es)	1969-05-07	1972-12-01	Procedimiento para la obtencion de derivados de indenopiri-dina.
ES409196A ES409196A1 (es)	1969-05-07	1972-12-01	Procedimiento para la obtencion de sales de adicion de aci-do de derivados de indenopiridina.
MY239/75A MY7500239A (en)	1969-05-07	1975-12-30	Indenopyridine derivatives

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH696769A CH516558A (de)	1969-05-07	1969-05-07	Verfahren zur Herstellung neuer Indenopyridinderivate

Publications (1)

Publication Number	Publication Date
CH516558A true CH516558A (de)	1971-12-15

Family

ID=4317847

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH696769A CH516558A (de)	1969-05-07	1969-05-07	Verfahren zur Herstellung neuer Indenopyridinderivate
CH870171A CH520141A (de)	1969-05-07	1969-05-07	Verfahren zur Herstellung neuer Indenopyridinderivate
CH870271A CH520142A (de)	1969-05-07	1969-05-07	Verfahren zur Herstellung neuer Indenopyridinderivate

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH870171A CH520141A (de)	1969-05-07	1969-05-07	Verfahren zur Herstellung neuer Indenopyridinderivate
CH870271A CH520142A (de)	1969-05-07	1969-05-07	Verfahren zur Herstellung neuer Indenopyridinderivate

Country Status (6)

Country	Link
AT (1)	AT313898B (cs)
CH (3)	CH516558A (cs)
CS (2)	CS164266B2 (cs)
PL (1)	PL80561B1 (cs)
SU (2)	SU383293A3 (cs)
ZA (1)	ZA703062B (cs)

1969
- 1969-05-07 CH CH696769A patent/CH516558A/de not_active IP Right Cessation
- 1969-05-07 CH CH870171A patent/CH520141A/de not_active IP Right Cessation
- 1969-05-07 CH CH870271A patent/CH520142A/de not_active IP Right Cessation
1970
- 1970-05-05 CS CS3110A patent/CS164266B2/cs unknown
- 1970-05-05 PL PL1970140430A patent/PL80561B1/pl unknown
- 1970-05-05 SU SU1435714A patent/SU383293A3/ru active
- 1970-05-05 SU SU1839956A patent/SU517256A3/ru active
- 1970-05-05 CS CS3286A patent/CS164267B2/cs unknown
- 1970-05-06 ZA ZA703062A patent/ZA703062B/xx unknown
- 1970-05-06 AT AT410570A patent/AT313898B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
SU517256A3 (ru)	1976-06-05
PL80561B1 (cs)	1975-08-30
CH520141A (de)	1972-03-15
CS164266B2 (cs)	1975-11-07
CH520142A (de)	1972-03-15
SU383293A3 (cs)	1973-05-25
AT313898B (de)	1974-03-11
CS164267B2 (cs)	1975-11-07
ZA703062B (en)	1971-12-29

Legal Events

Date	Code	Title	Description
1977-12-15	PL	Patent ceased

Publication	Publication Date	Title
DE1670480C2 (de)	1983-06-01	Pyrido[1,2-a]pyrimidinderivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende pharmazeutische Präparate
DE1795613A1 (de)	1972-03-30	Indolylessigsaeuren,Verfahren zu ihrer Herstellung und Arzneipraeparate
CH651563A5 (de)	1985-09-30	Hydroxyimino-oktahydro-indolo(2,3-a)chinolizin-derivate sowie verfahren zu ihrer herstellung.
DE2536003C2 (de)	1985-11-14	Pyrazol-Derivate, ihre Herstellung und diese enthaltende pharmazeutische Derivate
DE2617955A1 (de)	1976-11-18	Neue l-substituierte -aroyl-4-hydroxypiperidine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2931105C2 (cs)	1988-10-13
DE2021747A1 (de)	1970-11-19	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
CH516558A (de)	1971-12-15	Verfahren zur Herstellung neuer Indenopyridinderivate
DE3129718C2 (cs)	1988-08-18
DE2404924A1 (de)	1974-08-22	Ergolinderivate
AT384221B (de)	1987-10-12	Verfahren zur herstellung von neuen 3-substituierten tetrahydro-pyrrolo(1,2-a) pyrimidin-derivaten sowie von deren saeureadditions- und quaternaeren salzen
AT276383B (de)	1969-11-25	Verfahren zur Herstellung von neuen Phenylisoindolderivaten und deren Salzen
DE1695617A1 (de)	1971-04-22	Verfahren zur Herstellung von neuen Dibenzocycloheptatrienderivaten
DE2136702A1 (cs)	1972-01-27
CH621114A5 (en)	1981-01-15	Process for the preparation of 10,11-dihydro-3-carboxy- cyproheptadine and its N-oxide
DE1568253C (de)	1973-02-22	N substituierte 1,2 Diphenyl 2 acyloxy 3 amino methyl butene
AT360990B (de)	1981-02-10	Verfahren zur herstellung des neuen 1-methyl-4- (3-carboxy-10,11-dihydro-5h-dibenzo-(a,d)- -cyclohepten-5-yliden)-piperidin (10,11-dihydro -3-carboxy-cyproheptadin), seines n-oxids und seiner salze
AT330779B (de)	1976-07-26	Verfahren zur herstellung von neuen chinolinessigsaurederivaten und ihren salzen
DE2312256C3 (de)	1977-10-27	5-Pyrazol-essigsäurederivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Mittel
DE1695381B2 (de)	1973-03-08	Phthalazino eckige klammer auf 2,3-b eckige klammer zu phthalazine und ein verfahren zu ihrer herstellung
CH532014A (de)	1972-12-31	Verfahren zur Herstellung neuer, in Stellung 5 substituierter 5H-Dibenzo(a,d)cycloheptene
DE1295562B (de)	1969-05-22	Verfahren zur Herstellung von antiphlogistisch wirksamen, im Acylrest basisch substituierten 1-Phenyl-2, 3-dimethyl-4-acylamino-pyrazolon-(5)-derivaten
CH543506A (de)	1973-10-31	Verfahren zur Herstellung neuer Phenylpiperidinderivate
CH543507A (de)	1973-10-31	Verfahren zur Herstellung eines neuen Phenylpiperidinderivates
DE2813895A1 (de)	1978-10-19	Neue 2,4,6-trisubstituierte 2,3- dihydrobenzofuranderivate