GB1586578A - Process for the preparation of 2-(n-(2-hydroxyyethyl)-n-lower alkylaminomethyl) benzhydrols - Google Patents
Process for the preparation of 2-(n-(2-hydroxyyethyl)-n-lower alkylaminomethyl) benzhydrols Download PDFInfo
- Publication number
- GB1586578A GB1586578A GB33006/77A GB3300677A GB1586578A GB 1586578 A GB1586578 A GB 1586578A GB 33006/77 A GB33006/77 A GB 33006/77A GB 3300677 A GB3300677 A GB 3300677A GB 1586578 A GB1586578 A GB 1586578A
- Authority
- GB
- United Kingdom
- Prior art keywords
- process according
- compound
- methyl
- formula
- alkanoic acid
- 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
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical class C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 32
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 18
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- GKJLBCCOYHLILR-UHFFFAOYSA-N 2-phenyl-3h-4,1-benzoxazocine Chemical class C1OC=CC2=CC=CC=C2N=C1C1=CC=CC=C1 GKJLBCCOYHLILR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012442 inert solvent Substances 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 239000011737 fluorine Substances 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 230000009467 reduction Effects 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000006722 reduction reaction Methods 0.000 description 14
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000002002 slurry Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 239000003638 chemical reducing agent Substances 0.000 description 3
- NHTAQNXZFMZXBU-UHFFFAOYSA-N 2-[[2-[hydroxy(phenyl)methyl]phenyl]methyl-methylamino]ethanol Chemical compound OCCN(C)CC1=CC=CC=C1C(O)C1=CC=CC=C1 NHTAQNXZFMZXBU-UHFFFAOYSA-N 0.000 description 2
- BFVYSPGKIADILF-UHFFFAOYSA-N 2-benzoyl-n-(2-chloroethyl)-n-methylbenzamide Chemical compound ClCCN(C)C(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 BFVYSPGKIADILF-UHFFFAOYSA-N 0.000 description 2
- YQOHPRYMRZWLTA-UHFFFAOYSA-N 2-benzoyl-n-(2-hydroxyethyl)-n-methylbenzamide Chemical compound OCCN(C)C(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 YQOHPRYMRZWLTA-UHFFFAOYSA-N 0.000 description 2
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 231100001261 hazardous Toxicity 0.000 description 2
- 238000010667 large scale reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- -1 see British Patent 1 Chemical compound 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- RJGUJPSNJFGFLK-UHFFFAOYSA-N 1,1-dichloroethane;hydrochloride Chemical compound Cl.CC(Cl)Cl RJGUJPSNJFGFLK-UHFFFAOYSA-N 0.000 description 1
- KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical compound ClC=CCl KFUSEUYYWQURPO-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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- KQJGNHWFPBAXDJ-UHFFFAOYSA-N 5-methyl-1-phenyl-2,3,5,6-tetrahydro-4,1-benzoxazocine Chemical compound C1COC(C)CC2=CC=CC=C2N1C1=CC=CC=C1 KQJGNHWFPBAXDJ-UHFFFAOYSA-N 0.000 description 1
- OFDQCEZXTHTCFV-UHFFFAOYSA-N 5-methyl-1-phenyl-2,3,5,6-tetrahydro-4,1-benzoxazocine;hydrobromide Chemical compound Br.C1COC(C)CC2=CC=CC=C2N1C1=CC=CC=C1 OFDQCEZXTHTCFV-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 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
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical group [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/22—Eight-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33006/77A GB1586578A (en) | 1977-08-05 | 1977-08-05 | Process for the preparation of 2-(n-(2-hydroxyyethyl)-n-lower alkylaminomethyl) benzhydrols |
| SE7808337A SE441826B (sv) | 1977-08-05 | 1978-08-02 | Sett att framstella en 2/n-(2-hydroxietyl)-n-legre alkylaminometyl/benshydrol |
| NO782643A NO146023C (no) | 1977-08-05 | 1978-08-02 | Fremgangsmaate ved fremstilling av 2-(n-(2-hydroxyethyl)-n-lavere alkylaminomethyl)benzhydroler |
| NL787808113A NL7808113A (nl) | 1977-08-05 | 1978-08-02 | Werkwijze voor de bereiding van 2-(n-(2- hydroxyethyl)- -n-lager alkylaminomethyl)- benzhydrolen. |
| DK342278A DK149120C (da) | 1977-08-05 | 1978-08-02 | Fremgangsmaade til fremstilling af 2-(n-(2-hydroxyethyl)-n-alkylaminomethyl)benzhydroler |
| ES472301A ES472301A1 (es) | 1977-08-05 | 1978-08-02 | Procedimiento para preparar benzhidroles |
| CA000308679A CA1117551A (en) | 1977-08-05 | 1978-08-03 | Process for the preparation of 2-[n-(2- hydroxyethyl)-n-lower alkylaminomethyl]-benzhydrols |
| DE2834312A DE2834312C2 (de) | 1977-08-05 | 1978-08-04 | Verfahren zur Herstellung von 2[N-(2-Hydroxyäthyl)-N-niederalkylaminomethyl]-benzhydrolen |
| IT7826533A IT7826533A0 (it) | 1977-08-05 | 1978-08-04 | Processo per la preparazione di 2-aperta par. quadrata n-(2-idrossietil)-n-alchil(inferiore)aminometil chiusa par.quadrata-benzidroli. |
| PL1978208868A PL111230B1 (en) | 1977-08-05 | 1978-08-04 | Method of manufacturing lower 2-n-/2-hydroxyethyl/n-alkylaminoethyl-benzhydrols |
| JP53095155A JPS5839145B2 (ja) | 1977-08-05 | 1978-08-04 | ２↓−〔ｎ↓−（２↓−ヒドロキシエチル）↓−ｎ↓−低級アルキルアミノメチル〕↓−ベンツヒドロ−ルの製造法 |
| BE189728A BE869550A (fr) | 1977-08-05 | 1978-08-04 | Procedes de preparation et d'utilisation de 2-(n-(2-hydroxyethyl)-n-alkyl inferieur-aminomethyl) benzhydrols |
| IL55286A IL55286A (en) | 1977-08-05 | 1978-08-04 | Preparation of 2- n-(2-hydroxy-ethyl-)-n-lower alkylamino methyl benzhydrols |
| FI782404A FI67536C (fi) | 1977-08-05 | 1978-08-04 | Foerfarande foer framstaellning av 2-(n-(2-hydroxetyl)-n-alkylaminometyl)-bensohydrolderivat |
| CS785140A CS202017B2 (en) | 1977-08-05 | 1978-08-04 | Process for preparing 1-phenyl-1,3,4,6-tetrahydrobenzoxazocines |
| ZA00784437A ZA784437B (en) | 1977-08-05 | 1978-08-04 | Process for the preparation of 2-(n-(2-hydroxyethyl)-n-lower alkylaminomethyl)benzhydrols |
| SU782645753A SU984403A3 (ru) | 1977-08-05 | 1978-08-04 | Способ получени 2-[N-/2-оксиэтил/-N-/низший/-алкиламинометил]-бензгидрола |
| HU78RI681A HU175657B (hu) | 1977-08-05 | 1978-08-04 | Sposob poluchenija 2-/n-/2-gidroksiethil/-n-alkil korotkoj uglerodnoj cepi-aminometil/-benzgidrolov |
| AT569678A AT358010B (de) | 1977-08-05 | 1978-08-04 | Verfahren zur herstellung von 2(n-(2-hydroxy- aethyl)-n-niederalkylaminomethyl)-benzhydrolen |
| CH830178A CH634819A5 (en) | 1977-08-05 | 1978-08-04 | Process for the preparation of 2-[N-(2-hydroxyethyl)-N-lower alkyl-amino methyl]-benzhydrols. |
| MX787290U MX5783E (es) | 1977-08-05 | 1978-08-04 | Proceso para la preparacion de 2-(n-(2-hidroxietil)-n-alquilo inferior-aminometil)benzhidroles |
| NZ188068A NZ188068A (en) | 1977-08-05 | 1978-08-04 | Preparation of 2-(n-(2-hydrocyethyl)-n-loweralkylaminomethyl)-benzhydrol |
| FR7823129A FR2399405A1 (fr) | 1977-08-05 | 1978-08-04 | Procede de preparation et d'utilisation de 2-(n-(2-hydroxyethyl)-n-alkyl inferieur-aminomethyl) benzhydrols |
| AU38633/78A AU524563B2 (en) | 1977-08-05 | 1978-08-04 | Process for the preparation of 2-[n-hydroxyethyl] benzhydrols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33006/77A GB1586578A (en) | 1977-08-05 | 1977-08-05 | Process for the preparation of 2-(n-(2-hydroxyyethyl)-n-lower alkylaminomethyl) benzhydrols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1586578A true GB1586578A (en) | 1981-03-18 |
Family
ID=10347271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB33006/77A Expired GB1586578A (en) | 1977-08-05 | 1977-08-05 | Process for the preparation of 2-(n-(2-hydroxyyethyl)-n-lower alkylaminomethyl) benzhydrols |
Country Status (24)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI800076A (fi) * | 1980-01-11 | 1981-07-12 | Farmos Oy | Foerfarande foer framstaellning av benzhydrolderivat |
| DE3206660A1 (de) * | 1982-02-25 | 1983-09-01 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von o-acylamidomethylbenzyl-halogeniden |
| JP2006522012A (ja) * | 2002-12-20 | 2006-09-28 | アラキス リミテッド | ベンゾキサゾシンおよびそのモノアミン再吸収阻害剤としての用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3830803A (en) * | 1965-05-10 | 1974-08-20 | Riker Laboratories Inc | 5-loweralkyl-1-phenyl-1,3,4,6-tetrahydro-5h-benz(f)-2,5-oxazocines and 4-ones |
| GB1391862A (en) * | 1973-04-04 | 1975-04-23 | Yeda Res & Dev | Benzodiazepines |
-
1977
- 1977-08-05 GB GB33006/77A patent/GB1586578A/en not_active Expired
-
1978
- 1978-08-02 NO NO782643A patent/NO146023C/no unknown
- 1978-08-02 SE SE7808337A patent/SE441826B/sv not_active IP Right Cessation
- 1978-08-02 ES ES472301A patent/ES472301A1/es not_active Expired
- 1978-08-02 NL NL787808113A patent/NL7808113A/xx active Search and Examination
- 1978-08-02 DK DK342278A patent/DK149120C/da not_active IP Right Cessation
- 1978-08-03 CA CA000308679A patent/CA1117551A/en not_active Expired
- 1978-08-04 SU SU782645753A patent/SU984403A3/ru active
- 1978-08-04 BE BE189728A patent/BE869550A/xx not_active IP Right Cessation
- 1978-08-04 HU HU78RI681A patent/HU175657B/hu unknown
- 1978-08-04 FR FR7823129A patent/FR2399405A1/fr active Granted
- 1978-08-04 JP JP53095155A patent/JPS5839145B2/ja not_active Expired
- 1978-08-04 MX MX787290U patent/MX5783E/es unknown
- 1978-08-04 ZA ZA00784437A patent/ZA784437B/xx unknown
- 1978-08-04 PL PL1978208868A patent/PL111230B1/pl unknown
- 1978-08-04 DE DE2834312A patent/DE2834312C2/de not_active Expired
- 1978-08-04 FI FI782404A patent/FI67536C/fi not_active IP Right Cessation
- 1978-08-04 IT IT7826533A patent/IT7826533A0/it unknown
- 1978-08-04 IL IL55286A patent/IL55286A/xx active IP Right Grant
- 1978-08-04 AU AU38633/78A patent/AU524563B2/en not_active Expired
- 1978-08-04 NZ NZ188068A patent/NZ188068A/xx unknown
- 1978-08-04 AT AT569678A patent/AT358010B/de not_active Expired
- 1978-08-04 CS CS785140A patent/CS202017B2/cs unknown
- 1978-08-04 CH CH830178A patent/CH634819A5/de not_active IP Right Cessation
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| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19980518 |