CH622795A5 - - Google Patents

Download PDF

Info

Publication number: CH622795A5
Authority: CH; Switzerland
Prior art keywords: compounds; formula; radical; hydrogen atom; compound
Prior art date: 1976-04-13

Application number

CH450777A

Other languages

English (en)

French (fr)

Inventor

Gabor Istvan Koletar

Henry Najer

Jean-Pierre Gaston Lefevre

Regis Dupont

Don Pierre Rene Luc Giudicelli

Claude Constant Henri Morel

Original Assignee

Synthelabo

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.)

1976-04-13

Filing date

1977-04-12

Publication date

1981-04-30

1976-04-13 Priority claimed from FR7610773A external-priority patent/FR2358146A1/fr

1976-06-01 Priority claimed from FR7616445A external-priority patent/FR2353550A2/fr

1976-10-27 Priority claimed from FR7632319A external-priority patent/FR2368955A2/fr

1976-12-24 Priority claimed from FR7639035A external-priority patent/FR2374905A2/fr

1977-03-11 Priority claimed from FR7707249A external-priority patent/FR2383182A2/fr

1977-03-11 Priority claimed from FR7707248A external-priority patent/FR2383181A2/fr

1977-04-12 Application filed by Synthelabo filed Critical Synthelabo

1981-04-30 Publication of CH622795A5 publication Critical patent/CH622795A5/fr

Links

150000001875 compounds Chemical class 0.000 claims description 74
238000000034 method Methods 0.000 claims description 37
-1 alkyl radicals Chemical class 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 14
230000008569 process Effects 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
239000011707 mineral Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
241000764238 Isis Species 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
230000009471 action Effects 0.000 claims description 4
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
239000012279 sodium borohydride Substances 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims 7
150000005054 naphthyridines Chemical class 0.000 claims 6
APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 claims 6
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 4
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 4
150000007524 organic acids Chemical class 0.000 claims 4
235000005985 organic acids Nutrition 0.000 claims 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
239000003153 chemical reaction reagent Substances 0.000 claims 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
230000008030 elimination Effects 0.000 claims 2
238000003379 elimination reaction Methods 0.000 claims 2
229910052731 fluorine Inorganic materials 0.000 claims 2
239000011737 fluorine Substances 0.000 claims 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid group Chemical group C(CCCC(=O)O)(=O)O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 2
125000006277 halobenzyl group Chemical group 0.000 claims 2
125000002734 organomagnesium group Chemical group 0.000 claims 2
150000003254 radicals Chemical class 0.000 claims 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
238000004440 column chromatography Methods 0.000 claims 1
230000018044 dehydration Effects 0.000 claims 1
238000006297 dehydration reaction Methods 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
125000000468 ketone group Chemical group 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
150000007522 mineralic acids Chemical class 0.000 claims 1
101150009274 nhr-1 gene Proteins 0.000 claims 1
239000001384 succinic acid Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000000155 melt Substances 0.000 description 13
238000010586 diagram Methods 0.000 description 10
238000003756 stirring Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000000706 filtrate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 3
206010002660 Anoxia Diseases 0.000 description 3
241000976983 Anoxia Species 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
206010021143 Hypoxia Diseases 0.000 description 3
231100000111 LD50 Toxicity 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
230000007953 anoxia Effects 0.000 description 3
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 3
230000004083 survival effect Effects 0.000 description 3
238000012360 testing method Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
230000009466 transformation Effects 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-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
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical compound OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
102100025854 Acyl-coenzyme A thioesterase 1 Human genes 0.000 description 1
101710175445 Acyl-coenzyme A thioesterase 1 Proteins 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
238000000585 Mann–Whitney U test Methods 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
CPYGBGOXCJJJGC-GKLGUMFISA-L alcuronium chloride Chemical compound [Cl-].[Cl-].C/1([C@@H]23)=C\N([C@H]4\5)C6=CC=CC=C6[C@]4(CC[N@@+]4(CC=C)C\C6=C\CO)[C@@H]4C[C@@H]6C/5=C/N3C3=CC=CC=C3[C@@]22CC[N@@+]3(CC=C)C/C(=C/CO)[C@@H]\1C[C@H]32 CPYGBGOXCJJJGC-GKLGUMFISA-L 0.000 description 1
230000036626 alertness Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000000496 anti-anoxic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000007654 immersion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
208000014674 injury Diseases 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000002690 local anesthesia Methods 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006213 oxygenation reaction Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
230000036387 respiratory rate Effects 0.000 description 1
238000007790 scraping Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000008733 trauma Effects 0.000 description 1
208000009999 tuberous sclerosis Diseases 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1
229940072358 xylocaine Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Neurology (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Cardiology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH450777A 1976-04-13 1977-04-12 CH622795A5 (de)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
FR7610773A FR2358146A1 (fr)	1976-04-13	1976-04-13	Derives de la tetrahydro-1,2,3,3a indolo(3,2,1-de) (1,5)naphtyridine
FR7616445A FR2353550A2 (fr)	1976-06-01	1976-06-01	Procede de preparation de derives de naphtyridine
FR7632319A FR2368955A2 (fr)	1976-10-27	1976-10-27	Derives de la tetrahydro-1,2,3,3a indolo (3,2,1-de) (1,5) naphtyridine
FR7639035A FR2374905A2 (fr)	1976-12-24	1976-12-24	Derives de naphtyridine
FR7707249A FR2383182A2 (fr)	1977-03-11	1977-03-11	Nouveaux derives de naphtyridine
FR7707248A FR2383181A2 (fr)	1977-03-11	1977-03-11	Derives de naphtyridine

Publications (1)

Publication Number	Publication Date
CH622795A5 true CH622795A5 (de)	1981-04-30

Family

ID=27546337

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH450777A CH622795A5 (de)	1976-04-13	1977-04-12

Country Status (24)

Country	Link
US (1)	US4190657A (de)
JP (1)	JPS5823877B2 (de)
AR (1)	AR214519A1 (de)
AU (1)	AU506031B2 (de)
CA (1)	CA1072960A (de)
CH (1)	CH622795A5 (de)
DD (1)	DD129791A5 (de)
DE (1)	DE2716190A1 (de)
DK (1)	DK143703C (de)
FI (2)	FI63404C (de)
GB (1)	GB1543283A (de)
GR (1)	GR63658B (de)
IE (1)	IE44989B1 (de)
IL (1)	IL51853A (de)
LU (1)	LU77100A1 (de)
MT (1)	MTP811B (de)
MX (1)	MX5340E (de)
NO (1)	NO146777C (de)
NZ (1)	NZ183846A (de)
PL (1)	PL197373A1 (de)
PT (1)	PT66428B (de)
SE (2)	SE432932B (de)
SU (1)	SU655314A3 (de)
YU (1)	YU94877A (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5337696A (en) *	1976-08-26	1978-04-06	Omnium Chimique Sa	Hexahydrocantinonee6 derivative
US4228168A (en) *	1978-11-22	1980-10-14	Tanabe Seiyaku Co., Ltd.	Azepino [1,2,3-lm]-β-carboline compounds and pharmaceutical composition thereof
US4367230A (en) *	1980-01-04	1983-01-04	Tanabe Seiyaku Co., Ltd.	Novel triazafluoranthene compound and processes for preparing the same
FR2494693A1 (fr) *	1980-11-21	1982-05-28	Synthelabo	Derives de l'hexahydro-2,3,3a,4,5,6 1h-indolo(3,2,1-de)(naphtyridine-1,5), leur preparation et leur application en therapeutique
FR2517679A1 (fr) *	1981-12-03	1983-06-10	Synthelabo	Derives de diaza-3,7a cyclohepta (j,k) fluorenes, leur preparation et leur application en therapeutique
LU84664A1 (fr) *	1983-02-25	1984-11-08	Onmichem S A	Alkyl-4-indolonaphtyridines et leur application therapeutique
EP0347980A1 (de) *	1988-06-20	1989-12-27	Duphar International Research B.V	8,9-Anellierte B-Carboline und 8,9-anellierte 3,4-dihydro-B-Carboline
CN103193776A (zh) *	2013-04-16	2013-07-10	苏州维泰生物技术有限公司	一种具有抗肿瘤疗效的新型萘啶衍生物的合成方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3299078A (en) *	1962-10-01	1967-01-17	Smith Kline French Lab	Pyrido [3', 4': 4, 5] pyrrolo [3, 2, 1-hi] indoles and-[3, 2, 1-ij] quinolines
US3555018A (en) *	1968-12-03	1971-01-12	Ayerst Mckenna & Harrison	Thiazinopyridoindolone derivatives

1977
- 1977-04-07 DD DD7700198314A patent/DD129791A5/de unknown
- 1977-04-11 JP JP52041904A patent/JPS5823877B2/ja not_active Expired
- 1977-04-11 US US05/786,557 patent/US4190657A/en not_active Expired - Lifetime
- 1977-04-11 MT MT811A patent/MTP811B/xx unknown
- 1977-04-11 YU YU00948/77A patent/YU94877A/xx unknown
- 1977-04-11 IL IL51853A patent/IL51853A/xx unknown
- 1977-04-12 CH CH450777A patent/CH622795A5/fr not_active IP Right Cessation
- 1977-04-12 AU AU24189/77A patent/AU506031B2/en not_active Expired
- 1977-04-12 NO NO77771263A patent/NO146777C/no unknown
- 1977-04-12 DK DK161377A patent/DK143703C/da not_active IP Right Cessation
- 1977-04-12 GB GB15165/77A patent/GB1543283A/en not_active Expired
- 1977-04-12 SE SE7704172A patent/SE432932B/xx unknown
- 1977-04-12 LU LU77100A patent/LU77100A1/xx unknown
- 1977-04-12 AR AR267179A patent/AR214519A1/es active
- 1977-04-12 CA CA275,948A patent/CA1072960A/en not_active Expired
- 1977-04-12 DE DE19772716190 patent/DE2716190A1/de not_active Withdrawn
- 1977-04-12 MX MX775626U patent/MX5340E/es unknown
- 1977-04-12 PT PT66428A patent/PT66428B/pt unknown
- 1977-04-13 FI FI771159A patent/FI63404C/fi not_active IP Right Cessation
- 1977-04-13 SU SU772470258A patent/SU655314A3/ru active
- 1977-04-13 GR GR53198A patent/GR63658B/el unknown
- 1977-04-13 FI FI803790A patent/FI803790A7/fi not_active Application Discontinuation
- 1977-04-13 NZ NZ183846A patent/NZ183846A/xx unknown
- 1977-04-13 IE IE758/77A patent/IE44989B1/en unknown
- 1977-04-13 PL PL19737377A patent/PL197373A1/xx unknown
1982
- 1982-02-25 SE SE8201181A patent/SE8201181L/sv not_active Application Discontinuation

Also Published As

Publication number	Publication date
AU2418977A (en)	1978-10-19
DE2716190A1 (de)	1977-10-27
NZ183846A (en)	1980-09-12
IE44989B1 (en)	1982-06-02
NO146777B (no)	1982-08-30
MX5340E (es)	1983-06-27
DD129791A5 (de)	1978-02-08
FI771159A7 (de)	1977-10-14
JPS5823877B2 (ja)	1983-05-18
GR63658B (en)	1979-11-28
SE432932B (sv)	1984-04-30
DK143703C (da)	1982-04-13
AR214519A1 (es)	1979-06-29
YU94877A (en)	1983-01-21
IL51853A0 (en)	1977-06-30
PL197373A1 (pl)	1978-02-13
IL51853A (en)	1979-11-30
FI63404B (fi)	1983-02-28
AU506031B2 (en)	1979-12-13
IE44989L (en)	1977-10-13
FI803790A7 (fi)	1980-12-05
NO771263L (no)	1977-10-14
PT66428B (fr)	1978-09-20
US4190657A (en)	1980-02-26
MTP811B (en)	1978-02-20
DK143703B (da)	1981-09-28
JPS52125198A (en)	1977-10-20
GB1543283A (en)	1979-04-04
PT66428A (fr)	1977-05-01
SE8201181L (sv)	1982-05-25
SE7704172L (sv)	1977-10-14
SU655314A3 (ru)	1979-03-30
CA1072960A (en)	1980-03-04
FI63404C (fi)	1983-06-10
LU77100A1 (de)	1979-01-18
NO146777C (no)	1982-12-08
DK161377A (da)	1977-10-14

Legal Events

Date	Code	Title	Description
1985-12-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0031741A1 (de)	1981-07-08	Substituierte Iminosäuren, Verfahren zu ihrer Herstellung und ihre Verwendung als Enzym-Inhibitoren
EP0745586A1 (de)	1996-12-04	Aryl(alkyl)propylamide, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen, die sie enthalten
EP0172096A1 (de)	1986-02-19	3-Acylaminomethylimidazo [1,2-a] pyridine, dessen Herstellung und therapeutische Anwendung
FR2663934A1 (fr)	1992-01-03	Nouveaux derives de l'acide 4 - amino butyrique, leur procede de preparation et les preparations pharmaceutiques qui les contiennent.
EP0001534B1 (de)	1981-08-12	Pyrrolderivate, Verfahren zu ihrer Herstellung und ihre therapeutischen Verwendungen
CH622795A5 (de)	1981-04-30
EP0021857B1 (de)	1982-12-22	Indolderivate, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel
FR2460287A1 (fr)	1981-01-23	9-aminoalkylfluorenes, leur preparation et leur utilisation therapeutique
EP0239436B1 (de)	1990-06-20	Tricyclisches Derivat, nämlich 5-(3-Chloro-6-methyl-5,5-dioxo-6,11-dihydro-dibenzo[c,f] [1,2]-thiazepin-11-yl amino)-pentansäure, Verfahren zu seiner Herstellung und dieses enthaltende Arzneimittel
EP0089894B1 (de)	1986-06-11	N-(2-(4-Hydroxy-3-methoxy-phenyl)-2-Hydroxy-Ethyl)3-Amino-1-(1-Benzimidazolyl)-Butan und Salze und Hydrate mit Beta-adrenergischer Aktivität, therapeutische Anwendungen und Verfahren zu deren Herstellung
EP0130882B1 (de)	1987-01-07	Bicyclo(3.2.1)octancarbonsäure-Derivate, Verfahren zu ihren Herstellung und ihre therapeutische Verwendung
CA1093582A (fr)	1981-01-13	Procede d'obtention de nouvelles propylenediamines
CA1063619A (fr)	1979-10-02	Procede de preparation de nouveaux acides benzylamino alcanoiques et les produits qui en resultent
CH658786A5 (fr)	1986-12-15	Medicaments qui contiennent d'alpha-(n-pyrrolyl)-acides ou de leurs sels ou esters.
EP0082040B1 (de)	1986-01-15	3,7a-Diazacyclohepta(j,k)fluorenderivate, ihre Herstellung und ihre therapeutische Verwendung
CA2161284C (fr)	1999-05-18	Nouvelles o-arylmethyl n-(thio)acyl hydroxylamines, leurs procedes de preparation et les compisitions pharmaceutiques qui les contiennent
EP0061406B1 (de)	1984-06-13	Benzamido-alkyl-hydroxamsäurederivate, Verfahren zu ihrer Herstellung und pharmazeutische Mittel
FR2560873A1 (fr)	1985-09-13	Medicaments a base de derives de la piperidine, nouveaux derives de la piperidine et leurs procedes de preparation
EP0043811B1 (de)	1985-03-20	Indolonaphthyridine und ihre Verwendung als Arzneimittel
EP0001940A1 (de)	1979-05-16	Eburnameninderivate, ihre Herstellung und therapeutische Verwendung
CH618977A5 (de)	1980-08-29
LU86706A1 (fr)	1987-07-24	Nouveaux derives du benzo(4,5)cyclohepta(1,2-b)thiophene,leur preparation et leur utilisation comme medicaments
EP0534856A1 (de)	1993-03-31	Thienocyclopentanonoximether, ihre Herstellung und diese enthaltende Arzneimittel
BE884145R (fr)	1981-01-05	Composes indoliques nouveaux
LU83775A1 (fr)	1983-09-01	Derives de naphtyridine,leur preparation et leur application en therapeutique