GB1561153A - Process for the preparation of thiochroman derivatives - Google Patents
Process for the preparation of thiochroman derivatives Download PDFInfo
- Publication number
- GB1561153A GB1561153A GB35029/76A GB3502976A GB1561153A GB 1561153 A GB1561153 A GB 1561153A GB 35029/76 A GB35029/76 A GB 35029/76A GB 3502976 A GB3502976 A GB 3502976A GB 1561153 A GB1561153 A GB 1561153A
- Authority
- GB
- United Kingdom
- Prior art keywords
- process according
- thiochroman
- hydroxythiochroman
- general formula
- reaction
- 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
- 238000000034 method Methods 0.000 title abstract description 14
- WPWNEKFMGCWNPR-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene Chemical class C1=CC=C2CCCSC2=C1 WPWNEKFMGCWNPR-UHFFFAOYSA-N 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 150000001412 amines Chemical class 0.000 abstract description 8
- -1 glycerol halohydrin Chemical class 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- LJHYYURORLFPOJ-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromen-2-ol Chemical compound C1=CC=C2SC(O)CCC2=C1 LJHYYURORLFPOJ-UHFFFAOYSA-N 0.000 abstract description 5
- NULUVGRIIBHUOO-UHFFFAOYSA-N 3-(3,4-dihydro-2H-thiochromen-2-yloxy)propane-1,2-diol Chemical compound OC(COC1SC2=CC=CC=C2CC1)CO NULUVGRIIBHUOO-UHFFFAOYSA-N 0.000 abstract description 3
- 238000005576 amination reaction Methods 0.000 abstract description 3
- 230000000747 cardiac effect Effects 0.000 abstract description 2
- 150000003138 primary alcohols Chemical group 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 2
- 239000002876 beta blocker Substances 0.000 abstract 1
- 229940097320 beta blocking agent Drugs 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 230000033764 rhythmic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- RGGVNXXEMZOMQS-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromen-8-ol Chemical compound C1CCSC2=C1C=CC=C2O RGGVNXXEMZOMQS-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CZCBWCFCHLILAR-UHFFFAOYSA-N 3-(3,4-dihydro-2H-thiochromen-8-yloxy)propane-1,2-diol Chemical compound OC(COC=1C=CC=C2CCCSC12)CO CZCBWCFCHLILAR-UHFFFAOYSA-N 0.000 description 3
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- WJCTYFIAHVFXGY-UHFFFAOYSA-N 8-methoxy-2,3-dihydrothiochromen-4-one Chemical compound O=C1CCSC2=C1C=CC=C2OC WJCTYFIAHVFXGY-UHFFFAOYSA-N 0.000 description 2
- CQDQZADVAJJSAO-UHFFFAOYSA-N 8-methoxy-3,4-dihydro-2H-thiochromene Chemical compound COC=1C=CC=C2CCCSC12 CQDQZADVAJJSAO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SAYKZWPCENNSDR-UHFFFAOYSA-M (n-methylanilino)-triphenylphosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)N(C)C1=CC=CC=C1 SAYKZWPCENNSDR-UHFFFAOYSA-M 0.000 description 1
- YTFYDODBVNHGSQ-UHFFFAOYSA-N 2-(3,4-dihydro-2h-thiochromen-2-yloxymethyl)oxirane Chemical compound C1CC2=CC=CC=C2SC1OCC1CO1 YTFYDODBVNHGSQ-UHFFFAOYSA-N 0.000 description 1
- PYTANBUURZFYHD-UHFFFAOYSA-N 2-methylcyclopropan-1-amine Chemical compound CC1CC1N PYTANBUURZFYHD-UHFFFAOYSA-N 0.000 description 1
- DXSUORGKJZADET-UHFFFAOYSA-N 3,3-dimethylbutan-2-amine Chemical compound CC(N)C(C)(C)C DXSUORGKJZADET-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- WVYNIWHEHBSTSB-UHFFFAOYSA-N 3-methylhexan-2-amine Chemical compound CCCC(C)C(C)N WVYNIWHEHBSTSB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- LVZGQWKTUCVPBQ-UHFFFAOYSA-N acetic acid;trifluoroborane Chemical compound CC(O)=O.FB(F)F LVZGQWKTUCVPBQ-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical group 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
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)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB35029/76A GB1561153A (en) | 1976-08-23 | 1976-08-23 | Process for the preparation of thiochroman derivatives |
| YU1767/77A YU40169B (en) | 1976-08-23 | 1977-07-15 | Process for obtaining thiochromane derivatives |
| MX775969U MX5095E (es) | 1976-08-23 | 1977-08-08 | Procedimiento mejorado de obtencion de derivados del tiocromano |
| AR168797A AR215142A1 (es) | 1976-08-23 | 1977-08-15 | Procedimiento de obtencion de derivados del(3-amino monosubstituido-2-hidroxipropoxi)-tiocromano |
| PH20127A PH16402A (en) | 1976-08-23 | 1977-08-16 | Process for the preparation of thiochroman derivatives |
| ES461758A ES461758A1 (es) | 1976-08-23 | 1977-08-19 | Nuevo procedimiento de obtencion de derivados tiocromanicos. |
| OA56259A OA05744A (fr) | 1976-08-23 | 1977-08-20 | Procédé d'obtention de dérivés du thiochromanne |
| NLAANVRAGE7709229,A NL190521C (nl) | 1976-08-23 | 1977-08-22 | Werkwijze voor de bereiding van (3-amino-2-hydroxypropoxy)thiochromanderivaten. |
| JP9963177A JPS5325571A (en) | 1976-08-23 | 1977-08-22 | Production of thiochmaron derivatives |
| CA285,198A CA1103683A (fr) | 1976-08-23 | 1977-08-22 | Procede pour preparation de derives du thiochromane |
| CH1033677A CH623818A5 (en) | 1976-08-23 | 1977-08-23 | Process for producing derivatives of thiochroman |
| SU772514702A SU880251A3 (ru) | 1976-08-23 | 1977-08-23 | Способ получени производных тиохромана или их солей |
| HU77SI1588A HU178104B (en) | 1976-08-23 | 1977-08-23 | Process for producing tiochromane derivatives |
| HK86/84A HK8684A (en) | 1976-08-23 | 1984-02-01 | Process for the preparation of thiochroman derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB35029/76A GB1561153A (en) | 1976-08-23 | 1976-08-23 | Process for the preparation of thiochroman derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1561153A true GB1561153A (en) | 1980-02-13 |
Family
ID=10372964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35029/76A Expired GB1561153A (en) | 1976-08-23 | 1976-08-23 | Process for the preparation of thiochroman derivatives |
Country Status (14)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2530954A1 (fr) * | 1982-07-29 | 1984-02-03 | Adir | Composition pharmaceutique a base de 8-(3-tertbutylamino, 2-hydroxy-propoxy)-thiachromanne |
| FR2588260A1 (fr) * | 1985-10-04 | 1987-04-10 | Adir | Nouveau derive du thiochromanne, son procede de preparation et les compositions pharmaceutiques qui le contiennent |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5947574A (ja) * | 1982-09-08 | 1984-03-17 | Tlv Co Ltd | 多方向ボ−ル弁 |
| JPS63280785A (ja) * | 1987-05-14 | 1988-11-17 | Mitsui Toatsu Chem Inc | 構造用接着剤 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1308191A (en) * | 1970-04-06 | 1973-02-21 | Science Union & Cie | Thiochroman derivatives and a process for preparing them |
-
1976
- 1976-08-23 GB GB35029/76A patent/GB1561153A/en not_active Expired
-
1977
- 1977-07-15 YU YU1767/77A patent/YU40169B/xx unknown
- 1977-08-08 MX MX775969U patent/MX5095E/es unknown
- 1977-08-15 AR AR168797A patent/AR215142A1/es active
- 1977-08-16 PH PH20127A patent/PH16402A/en unknown
- 1977-08-19 ES ES461758A patent/ES461758A1/es not_active Expired
- 1977-08-20 OA OA56259A patent/OA05744A/xx unknown
- 1977-08-22 JP JP9963177A patent/JPS5325571A/ja active Granted
- 1977-08-22 CA CA285,198A patent/CA1103683A/fr not_active Expired
- 1977-08-22 NL NLAANVRAGE7709229,A patent/NL190521C/xx not_active IP Right Cessation
- 1977-08-23 HU HU77SI1588A patent/HU178104B/hu not_active IP Right Cessation
- 1977-08-23 CH CH1033677A patent/CH623818A5/fr not_active IP Right Cessation
- 1977-08-23 SU SU772514702A patent/SU880251A3/ru active
-
1984
- 1984-02-01 HK HK86/84A patent/HK8684A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2530954A1 (fr) * | 1982-07-29 | 1984-02-03 | Adir | Composition pharmaceutique a base de 8-(3-tertbutylamino, 2-hydroxy-propoxy)-thiachromanne |
| FR2588260A1 (fr) * | 1985-10-04 | 1987-04-10 | Adir | Nouveau derive du thiochromanne, son procede de preparation et les compositions pharmaceutiques qui le contiennent |
| EP0228920A1 (fr) * | 1985-10-04 | 1987-07-15 | Adir Et Compagnie | Nouveau dérivé du thiochromanne, son procédé de préparation et les compositions pharmaceutiques qui le contiennent |
| US4703057A (en) * | 1985-10-04 | 1987-10-27 | Adir Et Compagnie | Beta-blocking thiochroman derivatives, compositions and method of use therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS623150B2 (enrdf_load_stackoverflow) | 1987-01-23 |
| PH16402A (en) | 1983-09-22 |
| NL7709229A (nl) | 1978-02-27 |
| SU880251A3 (ru) | 1981-11-07 |
| YU176777A (en) | 1982-06-30 |
| ES461758A1 (es) | 1978-05-01 |
| AR215142A1 (es) | 1979-09-14 |
| YU40169B (en) | 1985-08-31 |
| HK8684A (en) | 1984-02-10 |
| JPS5325571A (en) | 1978-03-09 |
| OA05744A (fr) | 1981-05-31 |
| CH623818A5 (en) | 1981-06-30 |
| NL190521B (nl) | 1993-11-01 |
| MX5095E (es) | 1983-03-16 |
| HU178104B (en) | 1982-03-28 |
| NL190521C (nl) | 1994-04-05 |
| CA1103683A (fr) | 1981-06-23 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19950823 |