NO132478B - - Google Patents

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Info

Publication number: NO132478B
Authority: NO; Norway
Prior art keywords: formula; group; compounds; acid; lower alkyl
Prior art date: 1969-05-07

Application number

NO1707/70A

Other languages

English (en)

Norwegian (no)

Other versions

NO132478C (xx

Inventor

A Ebnoether

J-M Bastian

E 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

1970-05-05

Publication date

1975-08-11

1969-05-07 Priority claimed from CH696769A external-priority patent/CH516558A/de

1970-05-05 Application filed by Sandoz Ag filed Critical Sandoz Ag

1975-08-11 Publication of NO132478B publication Critical patent/NO132478B/no

1975-11-19 Publication of NO132478C publication Critical patent/NO132478C/no

Links

150000001875 compounds Chemical class 0.000 claims description 57
239000002253 acid Substances 0.000 claims description 26
238000000034 method Methods 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 5
125000001424 substituent group Chemical group 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
229910052794 bromium Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
150000003222 pyridines Chemical class 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
239000002023 wood Substances 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000010992 reflux Methods 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
150000007513 acids Chemical class 0.000 description 9
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 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000000155 melt Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
150000001649 bromium compounds Chemical class 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
150000004694 iodide salts Chemical class 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
230000007017 scission Effects 0.000 description 3
238000000926 separation method Methods 0.000 description 3
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
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
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
208000025865 Ulcer Diseases 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
150000004820 halides Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 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
125000006239 protecting group Chemical group 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
LCFFREMLXLZNHE-GBOLQPHISA-N (e)-2-[(3r)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile Chemical compound C12=C(N)N=CN=C2N([C@@H]2CCCN(C2)C(=O)C(/C#N)=C/C(C)(C)N2CCN(CC2)C2COC2)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 LCFFREMLXLZNHE-GBOLQPHISA-N 0.000 description 1
PFVFXDVOCHMQDU-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine-4-carboxylic acid Chemical class OC(=O)C1CCNC=C1 PFVFXDVOCHMQDU-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
SSORSZACHCNXSJ-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)-3-[2-(2-hydroxypropylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound ClC=1C=C(C=CC=1Cl)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NCC(C)O SSORSZACHCNXSJ-UHFFFAOYSA-N 0.000 description 1
AZYKGQOIAGPVCK-UHFFFAOYSA-N 3-pyridin-1-ium-2-ylpropanoate Chemical compound OC(=O)CCC1=CC=CC=N1 AZYKGQOIAGPVCK-UHFFFAOYSA-N 0.000 description 1
WSMRJBYOIBBOQN-UHFFFAOYSA-N 6-pyridin-2-ylhexanoic acid Chemical compound OC(=O)CCCCCC1=CC=CC=N1 WSMRJBYOIBBOQN-UHFFFAOYSA-N 0.000 description 1
PFWJFKBTIBAASX-UHFFFAOYSA-N 9h-indeno[2,1-b]pyridine Chemical class C1=CN=C2CC3=CC=CC=C3C2=C1 PFWJFKBTIBAASX-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
201000004624 Dermatitis Diseases 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
206010030113 Oedema 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
125000003342 alkenyl group Chemical group 0.000 description 1
-1 alkyl carboxylic acid Chemical class 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000000578 anorexic effect Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001741 anti-phlogistic effect Effects 0.000 description 1
208000010668 atopic eczema Diseases 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
210000004369 blood Anatomy 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
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
150000002440 hydroxy compounds Chemical class 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
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
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000002681 magnesium compounds Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
ZPCDIGGUGPUMON-UHFFFAOYSA-N methyl 3-pyridin-2-ylpropanoate Chemical compound COC(=O)CCC1=CC=CC=N1 ZPCDIGGUGPUMON-UHFFFAOYSA-N 0.000 description 1
KYLVAMSNNZMHSX-UHFFFAOYSA-N methyl 6-bromohexanoate Chemical compound COC(=O)CCCCCBr KYLVAMSNNZMHSX-UHFFFAOYSA-N 0.000 description 1
OJVSEHLMRCLAFY-UHFFFAOYSA-N methyl propanoate;hydrochloride Chemical compound Cl.CCC(=O)OC OJVSEHLMRCLAFY-UHFFFAOYSA-N 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
239000000203 mixture Substances 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000000546 pharmaceutical excipient Substances 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
230000002035 prolonged effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000009467 reduction Effects 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
230000001624 sedative effect Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
230000007306 turnover 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)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO1707/70A 1969-05-07 1970-05-05 NO132478C (xx)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH696769A CH516558A (de)	1969-05-07	1969-05-07	Verfahren zur Herstellung neuer Indenopyridinderivate
CH1842469		1969-12-11
CH165170		1970-02-05

Publications (2)

Publication Number	Publication Date
NO132478B true NO132478B (xx)	1975-08-11
NO132478C NO132478C (xx)	1975-11-19

Family

ID=27173145

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO1707/70A NO132478C (xx)	1969-05-07	1970-05-05

Country Status (14)

Country	Link
US (1)	US3678058A (xx)
CA (1)	CA951734A (xx)
CY (1)	CY819A (xx)
DE (1)	DE2021747A1 (xx)
ES (3)	ES379299A1 (xx)
FI (1)	FI51478C (xx)
FR (1)	FR2051503B1 (xx)
GB (1)	GB1306404A (xx)
IE (1)	IE35052B1 (xx)
IL (1)	IL34468A (xx)
MY (1)	MY7500239A (xx)
NL (1)	NL7006274A (xx)
NO (1)	NO132478C (xx)
SE (1)	SE375310B (xx)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3991066A (en) *	1971-01-26	1976-11-09	Sandoz Ltd.	1,3,4,9B-Tetrahydro-5-methyl-2H-indeno[1,2-c]pyridines
US5319084A (en) *	1993-08-16	1994-06-07	Research Triangle Institute	Hexahydroindenopyridine compounds having antispermatogenic activity
US7544696B2 (en)	2003-01-24	2009-06-09	Research Triangle Institute	Spermicidal and/or antifungal composition and methods of using the same
US7795436B2 (en) *	2005-08-24	2010-09-14	Bristol-Myers Squibb Company	Substituted tricyclic heterocycles as serotonin receptor agonists and antagonists

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3462443A (en) *	1967-04-19	1969-08-19	Mcneilab Inc	Indeno(1,2-c)pyridine derivatives

1970
- 1970-04-10 CY CY819A patent/CY819A/xx unknown
- 1970-04-10 GB GB1708070A patent/GB1306404A/en not_active Expired
- 1970-04-29 NL NL7006274A patent/NL7006274A/xx unknown
- 1970-04-30 US US33498A patent/US3678058A/en not_active Expired - Lifetime
- 1970-05-04 DE DE19702021747 patent/DE2021747A1/de active Pending
- 1970-05-04 FR FR7016162A patent/FR2051503B1/fr not_active Expired
- 1970-05-05 ES ES379299A patent/ES379299A1/es not_active Expired
- 1970-05-05 SE SE7006162A patent/SE375310B/xx unknown
- 1970-05-05 IL IL34468A patent/IL34468A/en unknown
- 1970-05-05 IE IE586/70A patent/IE35052B1/xx unknown
- 1970-05-05 NO NO1707/70A patent/NO132478C/no unknown
- 1970-05-05 FI FI701261A patent/FI51478C/fi active
- 1970-05-06 CA CA081,987,A patent/CA951734A/en not_active Expired
1972
- 1972-12-01 ES ES409197A patent/ES409197A1/es not_active Expired
- 1972-12-01 ES ES409196A patent/ES409196A1/es not_active Expired
1975
- 1975-12-30 MY MY239/75A patent/MY7500239A/xx unknown

Also Published As

Publication number	Publication date
CA951734A (en)	1974-07-23
MY7500239A (en)	1975-12-31
NL7006274A (xx)	1970-11-10
DE2021747A1 (de)	1970-11-19
IE35052L (en)	1970-11-07
CY819A (en)	1976-12-01
ES409196A1 (es)	1976-03-16
ES409197A1 (es)	1976-03-16
IL34468A0 (en)	1970-07-19
ES379299A1 (es)	1973-04-16
SE375310B (xx)	1975-04-14
FI51478B (xx)	1976-09-30
US3678058A (en)	1972-07-18
FI51478C (fi)	1977-01-10
IE35052B1 (en)	1975-10-29
IL34468A (en)	1973-06-29
NO132478C (xx)	1975-11-19
FR2051503A1 (xx)	1971-04-09
GB1306404A (en)	1973-02-14
FR2051503B1 (xx)	1974-08-30

Publication	Publication Date	Title
US3755340A (en)	1973-08-28	Amino derivatives of pyrazolopyridine carboxylic acids and esters
US3484445A (en)	1969-12-16	Derivatives of chromone-2-carboxylic acid
NO154116B (no)	1986-04-14	Fremgangsm¨te og lamellsepareringsapparat for tilf¯rsel og fordeling av en sammensatt v\|ske til et lamellseparerings apparat.
NO134212B (xx)	1976-05-24
US2540218A (en)	1951-02-06	2-hydroxy-pyridine-n-oxide and process for preparing same
NO146775B (no)	1982-08-30	Analogifremgangsmaate ved fremstilling av terapeutisk aktive racemiske eller optisk aktive kondenserte pyrimidinderivater
Hurd et al.	1970	Hydroxamic acids and N-hydroxyimides related to pyridine, pyrazine, and quinoxaline
NO132478B (xx)	1975-08-11
US3519628A (en)	1970-07-07	Aralkyl diazabicyclo(4,4,0)decanes
US3629265A (en)	1971-12-21	7-halo-4-isoquinolones
US2266754A (en)	1941-12-23	Synthesis of vitamin
EP0142754A2 (en)	1985-05-29	2-Substituted-benzoic acid imidazoles, process for preparing them and pharmaceutical compositions containing them
US2701251A (en)	1955-02-01	Process of producing indoleacetic acids and new indoleacetic acids produced thereby
US4036841A (en)	1977-07-19	Indolo[2,3α]quinolizine derivatives
NO118975B (xx)	1970-03-09
NO127920B (xx)	1973-09-03
US3972883A (en)	1976-08-03	1,6-Dimethyl-8β-[2' or 3'-pyrroyloxyethyl or substituted pyrroyloxyethyl]-10α-methoxyergolene compounds
US3928368A (en)	1975-12-23	Alcohol derivatives of pyrazolo{8 3,4-b{9 pyridines
SU982544A3 (ru)	1982-12-15	Способ получени 5,8-дигидро-5-этил-8-оксофуро (3,2в)-1,8-нафтиридин-7-карбоновой кислоты или ее соли
NO128995B (xx)	1974-02-11
US4044012A (en)	1977-08-23	Indolo-quinolizidine derivatives
US3470181A (en)	1969-09-30	Fused 2-pyrimidinepropionic acid compounds,related compounds,and the process for their preparation
US3474112A (en)	1969-10-21	Alpha-tetronic acid derivatives
NO781896L (no)	1978-12-04	4-fenyl-8-amino-tetrahydroisokinoliner, farmasoeytiske preparater som inneholder disse, fremgangsmaate til fremstilling av disse preparater og deres anvendelse som antidepresjonsmidler
US3475438A (en)	1969-10-28	Piperidine derivatives of dibenzobicyclo(5.1.0)octane