FR2527210A1 - Enantiomeres d'hexahydro-2,3,3a,4,5,6 1h-indolo(3,2,1-de) (naphtyridine-1,5), leur procede de separation et leur application en therapeutique - Google Patents
Enantiomeres d'hexahydro-2,3,3a,4,5,6 1h-indolo(3,2,1-de) (naphtyridine-1,5), leur procede de separation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2527210A1 FR2527210A1 FR8208632A FR8208632A FR2527210A1 FR 2527210 A1 FR2527210 A1 FR 2527210A1 FR 8208632 A FR8208632 A FR 8208632A FR 8208632 A FR8208632 A FR 8208632A FR 2527210 A1 FR2527210 A1 FR 2527210A1
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- FR
- France
- Prior art keywords
- enantiomers
- indolo
- acid
- hexahydro
- mixture
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical compound C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000000926 separation method Methods 0.000 title claims description 5
- 230000001225 therapeutic effect Effects 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 238000001640 fractional crystallisation Methods 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000001953 recrystallisation Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- -1 bis (4-methyl-benzoyloxy) -2,3-butanediol Chemical compound 0.000 claims description 7
- JHFAEUICJHBVHB-UHFFFAOYSA-N 1h-indol-2-ol Chemical compound C1=CC=C2NC(O)=CC2=C1 JHFAEUICJHBVHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- 239000003643 water by type Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 10
- 230000004083 survival effect Effects 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 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
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229960005137 succinic acid Drugs 0.000 description 3
- 238000012795 verification Methods 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- KIUPCUCGVCGPPA-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) carbonochloridate Chemical compound CC(C)C1CCC(C)CC1OC(Cl)=O KIUPCUCGVCGPPA-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 208000026680 Metabolic Brain disease Diseases 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000496 anti-anoxic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 231100000871 behavioral problem Toxicity 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 230000003434 inspiratory effect Effects 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 239000010502 orange oil Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000000287 tissue oxygenation Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 208000009999 tuberous sclerosis Diseases 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
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- 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
- C07D471/12—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 three hetero rings
- C07D471/16—Peri-condensed systems
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C—CHEMISTRY; METALLURGY
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- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/063—Complexes of boron halides
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/065—Organic compounds derived from inorganic acids or metal salts derived from Ti or Zr
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B1/00—Engines characterised by fuel-air mixture compression
- F02B1/02—Engines characterised by fuel-air mixture compression with positive ignition
- F02B1/04—Engines characterised by fuel-air mixture compression with positive ignition with fuel-air mixture admission into cylinder
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02F—CYLINDERS, PISTONS OR CASINGS, FOR COMBUSTION ENGINES; ARRANGEMENTS OF SEALINGS IN COMBUSTION ENGINES
- F02F7/00—Casings, e.g. crankcases
- F02F7/006—Camshaft or pushrod housings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8208632A FR2527210A1 (fr) | 1982-05-18 | 1982-05-18 | Enantiomeres d'hexahydro-2,3,3a,4,5,6 1h-indolo(3,2,1-de) (naphtyridine-1,5), leur procede de separation et leur application en therapeutique |
| NO831737A NO831737L (no) | 1982-05-18 | 1983-05-16 | Fremgangsmaate for fremstilling av indolo-naftyridinderivater |
| SE8302747A SE8302747L (sv) | 1982-05-18 | 1983-05-16 | Indol-naftyridiner |
| HU831720A HU189660B (en) | 1982-05-18 | 1983-05-17 | Process for the separation of enantiomers of 2,3,3a,4,5,6-hexahydro-1h-indolo/3,2,1-de/ 1,5-naphthyridine and for preparing pharmaceutical compositions containing such compounds |
| DE19833317961 DE3317961A1 (de) | 1982-05-18 | 1983-05-17 | Enantiomere von 2,3,3a,4,5,6-hexahydro-1h-indolo(3,2,1-de)(1,5-naphthyridin), verfahren zu ihrer trennung und sie enthaltende arzneimittel |
| AU14616/83A AU1461683A (en) | 1982-05-18 | 1983-05-17 | Enantiomers of hexahydra-1h-indolo (3,2,1-de)-(1,5- naphthyridine) |
| GB08313625A GB2120250A (en) | 1982-05-18 | 1983-05-17 | Enantiomers of 2,3,3a,4,5,6- hexahydro-1H-indolo(3,2,1- de)-[1,5-naphthyridine] |
| NL8301739A NL8301739A (nl) | 1982-05-18 | 1983-05-17 | Werkwijze voor het scheiden van enantiomeren van 2,3,3a,4,5,6-hexahydro 1h-indool 3,2,1-denaftyridine-1,5, de hexahydroenantiomeren en de therapeutische toepassing hiervan. |
| GR71371A GR78568B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-05-18 | 1983-05-17 | |
| IT21143/83A IT1194244B (it) | 1982-05-18 | 1983-05-17 | Enantiomeri di esaidro-2,3,3a,4,5,6 1h-indol (3,2,1-de) (naftiridina-1,5),processo di loro separazione e loro impiego in terapeutica |
| DK219183A DK219183A (da) | 1982-05-18 | 1983-05-17 | Enantiomere af 2,3,3a,4,5,6-hexahydro-1h-indolo(3,2,1-de)(1,5-naphthyridin), fremgangsmaade til deres adskillelse samt deres anvendelse |
| ES522478A ES522478A0 (es) | 1982-05-18 | 1983-05-17 | Procedimiento de separacion de los enantiomeros del hexahidro-2,3,3a,4,5,6-1h-indol(3,2,1-de) (naftiridina-1,5) |
| PT76716A PT76716B (fr) | 1982-05-18 | 1983-05-17 | Procede de preparation des enantiomeres de l'hexahydro-2,3,3a,4,5,6 1h-indolo <3,2,1-de><naphtyridine-1,5> |
| JP58086526A JPS58210083A (ja) | 1982-05-18 | 1983-05-17 | ナフチリジン誘導体のエナンチオマ− |
| IL68721A IL68721A0 (en) | 1982-05-18 | 1983-05-17 | Enantiomers of 2,3,3a,4,5,6-hexahydro-1h-indolo(3,2,1-de)-(1,5-naphthyridine),their preparation and pharmaceutical compositions containing them |
| BE0/210788A BE896764A (fr) | 1982-05-18 | 1983-05-17 | Enantiomeres d'hexahydro-2,3,3a,4,5,6 1h-indola [3,2,1-de] [naphtyridine 1,5] leur procede de separation et leur application en therapeutique. |
| ZA833539A ZA833539B (en) | 1982-05-18 | 1983-05-17 | Enantiomers of 2,3,3a,4,5,6-hexahydro-1h-indolo(3,2,1-de)(1,5-naphthyridine) |
| CH267983A CH654579B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-05-18 | 1983-05-17 | |
| LU84808A LU84808A1 (fr) | 1982-05-18 | 1983-05-17 | Enantiomeres d'hexahydro-2,3,3a,4,5,6 1h-indolo(3,2-1-de)(naphtyridine-1,5),leur procede de separation et leur application en therapeutique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8208632A FR2527210A1 (fr) | 1982-05-18 | 1982-05-18 | Enantiomeres d'hexahydro-2,3,3a,4,5,6 1h-indolo(3,2,1-de) (naphtyridine-1,5), leur procede de separation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2527210A1 true FR2527210A1 (fr) | 1983-11-25 |
| FR2527210B1 FR2527210B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-04-12 |
Family
ID=9274131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8208632A Granted FR2527210A1 (fr) | 1982-05-18 | 1982-05-18 | Enantiomeres d'hexahydro-2,3,3a,4,5,6 1h-indolo(3,2,1-de) (naphtyridine-1,5), leur procede de separation et leur application en therapeutique |
Country Status (19)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU84664A1 (fr) * | 1983-02-25 | 1984-11-08 | Onmichem S A | Alkyl-4-indolonaphtyridines et leur application therapeutique |
| US5231181A (en) * | 1991-03-21 | 1993-07-27 | Syntex (U.S.A.) Inc. | Process for the preparation of (8as,12as,13as)-decahydroisoquino ((2,1-g) (1,6)-naphthyridin-8-one derivatives |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0043811A1 (fr) * | 1980-07-03 | 1982-01-13 | OMNICHEM Société anonyme | Nouvelles indolonaphtyridines et leur utilisation en tant que médicaments |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1982
- 1982-05-18 FR FR8208632A patent/FR2527210A1/fr active Granted
-
1983
- 1983-05-16 NO NO831737A patent/NO831737L/no unknown
- 1983-05-16 SE SE8302747A patent/SE8302747L/xx not_active Application Discontinuation
- 1983-05-17 GR GR71371A patent/GR78568B/el unknown
- 1983-05-17 ZA ZA833539A patent/ZA833539B/xx unknown
- 1983-05-17 AU AU14616/83A patent/AU1461683A/en not_active Abandoned
- 1983-05-17 DE DE19833317961 patent/DE3317961A1/de not_active Withdrawn
- 1983-05-17 ES ES522478A patent/ES522478A0/es active Granted
- 1983-05-17 HU HU831720A patent/HU189660B/hu unknown
- 1983-05-17 BE BE0/210788A patent/BE896764A/fr not_active IP Right Cessation
- 1983-05-17 GB GB08313625A patent/GB2120250A/en not_active Withdrawn
- 1983-05-17 IL IL68721A patent/IL68721A0/xx unknown
- 1983-05-17 LU LU84808A patent/LU84808A1/fr unknown
- 1983-05-17 IT IT21143/83A patent/IT1194244B/it active
- 1983-05-17 PT PT76716A patent/PT76716B/pt unknown
- 1983-05-17 JP JP58086526A patent/JPS58210083A/ja active Pending
- 1983-05-17 NL NL8301739A patent/NL8301739A/nl not_active Application Discontinuation
- 1983-05-17 DK DK219183A patent/DK219183A/da not_active Application Discontinuation
- 1983-05-17 CH CH267983A patent/CH654579B/fr not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0043811A1 (fr) * | 1980-07-03 | 1982-01-13 | OMNICHEM Société anonyme | Nouvelles indolonaphtyridines et leur utilisation en tant que médicaments |
Also Published As
| Publication number | Publication date |
|---|---|
| SE8302747L (sv) | 1983-11-19 |
| LU84808A1 (fr) | 1985-03-21 |
| ES8403126A1 (es) | 1984-03-01 |
| IT8321143A0 (it) | 1983-05-17 |
| DE3317961A1 (de) | 1983-11-24 |
| GR78568B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-09-27 |
| ES522478A0 (es) | 1984-03-01 |
| DK219183D0 (da) | 1983-05-17 |
| GB8313625D0 (en) | 1983-06-22 |
| PT76716B (fr) | 1986-03-27 |
| SE8302747D0 (sv) | 1983-05-16 |
| ZA833539B (en) | 1984-02-29 |
| NO831737L (no) | 1983-11-21 |
| FR2527210B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-04-12 |
| JPS58210083A (ja) | 1983-12-07 |
| NL8301739A (nl) | 1983-12-16 |
| BE896764A (fr) | 1983-11-17 |
| IL68721A0 (en) | 1983-09-30 |
| AU1461683A (en) | 1983-11-24 |
| CH654579B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-02-28 |
| IT1194244B (it) | 1988-09-14 |
| HU189660B (en) | 1986-07-28 |
| GB2120250A (en) | 1983-11-30 |
| DK219183A (da) | 1983-11-19 |
| PT76716A (fr) | 1983-06-01 |
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