CA1101421A - Pyrano¬4,3-e| -as-triazines, their production and tranquilliser/sleep-inducer use - Google Patents
Pyrano¬4,3-e| -as-triazines, their production and tranquilliser/sleep-inducer useInfo
- Publication number
- CA1101421A CA1101421A CA320,759A CA320759A CA1101421A CA 1101421 A CA1101421 A CA 1101421A CA 320759 A CA320759 A CA 320759A CA 1101421 A CA1101421 A CA 1101421A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- isomer
- trifluoromethyl
- carbon atoms
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 239000000411 inducer Substances 0.000 title abstract description 5
- 239000003204 tranquilizing agent Substances 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 239000012298 atmosphere Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 241000282693 Cercopithecidae Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- -1 f luorine Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000000803 paradoxical effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010062519 Poor quality sleep Diseases 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000028527 righting reflex Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 229940116411 terpineol Drugs 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- WEQFQARMFHPBTG-UHFFFAOYSA-N 1,9,9-trimethyl-10-oxa-3,4,6-triazatricyclo[6.2.2.02,7]dodeca-2(7),3,5-triene Chemical class CC1(C2C=3N=CN=NC=3C(O1)(CC2)C)C WEQFQARMFHPBTG-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- MWVFXWACGIPVQI-UHFFFAOYSA-N 6-hydroxyimino-2,2,4-trimethyl-3-oxabicyclo[2.2.2]octan-5-one Chemical compound C1CC2C(C)(C)OC1(C)C(=O)C2=NO MWVFXWACGIPVQI-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000282668 Cebus Species 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- QQZWEECEMNQSTG-UHFFFAOYSA-N Ethyl nitrite Chemical compound CCON=O QQZWEECEMNQSTG-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000006172 aromatic nitration reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-O nitrosooxidanium Chemical compound [OH2+]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 229960002784 thioridazine Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Anesthesiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87494078A | 1978-02-03 | 1978-02-03 | |
| US874,940 | 1978-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1101421A true CA1101421A (en) | 1981-05-19 |
Family
ID=25364907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA320,759A Expired CA1101421A (en) | 1978-02-03 | 1979-02-02 | Pyrano¬4,3-e| -as-triazines, their production and tranquilliser/sleep-inducer use |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS54115399A (en, 2012) |
| AT (1) | AT374805B (en, 2012) |
| AU (1) | AU537176B2 (en, 2012) |
| BE (1) | BE873874R (en, 2012) |
| CA (1) | CA1101421A (en, 2012) |
| CH (1) | CH644863A5 (en, 2012) |
| DE (1) | DE2903130A1 (en, 2012) |
| DK (1) | DK35879A (en, 2012) |
| ES (2) | ES477430A1 (en, 2012) |
| FI (1) | FI790268A7 (en, 2012) |
| FR (1) | FR2416229A2 (en, 2012) |
| GB (1) | GB2013675B (en, 2012) |
| IE (1) | IE48044B1 (en, 2012) |
| IL (1) | IL56561A (en, 2012) |
| IT (1) | IT7947833A0 (en, 2012) |
| NL (1) | NL7900767A (en, 2012) |
| PH (1) | PH15532A (en, 2012) |
| PT (1) | PT69168A (en, 2012) |
| SE (1) | SE7900718L (en, 2012) |
| ZA (1) | ZA79459B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5681897A (en) * | 1979-12-06 | 1981-07-04 | Nippon Musical Instruments Mfg | Electronic musical instrument |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK139301B (da) * | 1974-05-01 | 1979-01-29 | Sandoz Ag | Analogifremgangsmåde til fremstilling af 5,5,7,7-tetramethylfuro(3,4-e)as-triaziner. |
-
1979
- 1979-01-25 CH CH76179A patent/CH644863A5/de not_active IP Right Cessation
- 1979-01-26 SE SE7900718A patent/SE7900718L/xx not_active Application Discontinuation
- 1979-01-26 DK DK35879A patent/DK35879A/da not_active Application Discontinuation
- 1979-01-26 FI FI790268A patent/FI790268A7/fi unknown
- 1979-01-27 DE DE19792903130 patent/DE2903130A1/de not_active Withdrawn
- 1979-01-31 IT IT7947833A patent/IT7947833A0/it unknown
- 1979-01-31 GB GB7903415A patent/GB2013675B/en not_active Expired
- 1979-01-31 NL NL7900767A patent/NL7900767A/xx not_active Application Discontinuation
- 1979-02-01 AU AU43864/79A patent/AU537176B2/en not_active Ceased
- 1979-02-01 JP JP978479A patent/JPS54115399A/ja active Pending
- 1979-02-01 IL IL56561A patent/IL56561A/xx unknown
- 1979-02-01 BE BE0/193219A patent/BE873874R/xx active
- 1979-02-01 PT PT7969168A patent/PT69168A/pt unknown
- 1979-02-01 IE IE196/79A patent/IE48044B1/en unknown
- 1979-02-02 ES ES477430A patent/ES477430A1/es not_active Expired
- 1979-02-02 ZA ZA79459A patent/ZA79459B/xx unknown
- 1979-02-02 AT AT0077579A patent/AT374805B/de not_active IP Right Cessation
- 1979-02-02 CA CA320,759A patent/CA1101421A/en not_active Expired
- 1979-02-02 FR FR7902744A patent/FR2416229A2/fr active Granted
- 1979-05-21 PH PH22525A patent/PH15532A/en unknown
-
1980
- 1980-01-31 ES ES488135A patent/ES8101593A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH644863A5 (de) | 1984-08-31 |
| JPS54115399A (en) | 1979-09-07 |
| ES488135A0 (es) | 1980-12-16 |
| GB2013675A (en) | 1979-08-15 |
| NL7900767A (nl) | 1979-08-07 |
| FI790268A7 (fi) | 1979-08-04 |
| AT374805B (de) | 1984-06-12 |
| ES8101593A1 (es) | 1980-12-16 |
| PT69168A (fr) | 1979-03-01 |
| ZA79459B (en) | 1980-02-27 |
| IE48044B1 (en) | 1984-09-05 |
| AU4386479A (en) | 1979-08-09 |
| IL56561A0 (en) | 1979-05-31 |
| PH15532A (en) | 1983-02-09 |
| SE7900718L (sv) | 1979-08-04 |
| DE2903130A1 (de) | 1979-08-09 |
| FR2416229A2 (fr) | 1979-08-31 |
| DK35879A (da) | 1979-08-04 |
| GB2013675B (en) | 1982-11-17 |
| ATA77579A (de) | 1983-10-15 |
| IL56561A (en) | 1982-07-30 |
| IE790196L (en) | 1979-08-03 |
| IT7947833A0 (it) | 1979-01-31 |
| ES477430A1 (es) | 1980-08-16 |
| BE873874R (fr) | 1979-08-01 |
| AU537176B2 (en) | 1984-06-14 |
| FR2416229B2 (en, 2012) | 1981-10-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4086243A (en) | Intermediates in the preparation of isoxazolyl benzamides | |
| EP0605622A1 (en) | Oxygen substituted derivatives of nucleophile-nitric oxide adducts as nitric oxide donor prodrugs | |
| EP0172096A1 (fr) | Dérivés d'acylaminométhyl-3 imidazo[1,2-a]pyridines, leur préparation et leur application en thérapeutique | |
| Standridge et al. | Phenylalkylamines with potential psychotherapeutic utility. 1. 2-Amino-1-(2, 5-dimethoxy-4-methylphenyl) butane | |
| KR910000640B1 (ko) | 중추 신경계에 활성을 나타내는 복소환 화합물의 제조방법 | |
| CA1101421A (en) | Pyrano¬4,3-e| -as-triazines, their production and tranquilliser/sleep-inducer use | |
| US3963713A (en) | Furo(3,4-e)-as-triazines and corresponding 4-oxides | |
| US4055643A (en) | Furo(3,4-E)-as-triazines and corresponding 4-oxides as sleep inducers and minor tranquilizers | |
| EP0063084A1 (fr) | Dérivés de phénéthanolamine, leur préparation et leur application en thérapeutique | |
| US4228280A (en) | Pyrano[4,3-e]-as-triazines and corresponding 4-oxides | |
| CA1095518A (en) | Pyrano-as-triazines | |
| US4379792A (en) | Anti-inflammatory composition | |
| NZ189537A (en) | Cup selection apparatus for vending machine | |
| JPS6330283B2 (en, 2012) | ||
| US3920687A (en) | 2,3,6,7-tetrahydro-6-phenyl-5h-imidazo(1,2-d)+8 1,4)benzodiazepin-5-ones and diazepines | |
| US3962240A (en) | Process for the preparation of furo(3,4-e)-as-triazines | |
| EP0045473B1 (en) | A pharmaceutical composition containing a benzofuran-carboxamide derivative as the active ingredient | |
| JPH0559087A (ja) | ウリジン誘導体及びこれを含有する医薬 | |
| PT94750A (pt) | Processo para a preparacao de benzoxazolonas 4,5,6,7-tetra-substituidas | |
| US3689523A (en) | Substituted haloalkanesulfonanilides | |
| US3946111A (en) | Pharmaceutical compositions containing 1 or 2-mono and dialkyl substituted thienobenzopyrans and pharmacological uses thereof | |
| JPS6258349B2 (en, 2012) | ||
| CA1041526A (en) | Alkyl substituted cyclopenta benzopyrans | |
| US4002751A (en) | 5-Hydrazinopyridazin-3(2H)-ones | |
| US4070468A (en) | 2-Amino-quinolin-4-one-3-phosphonic acid esters |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |