CH473138A - Verfahren zur Herstellung von neuen 9,10-Dihydro-4H-benzo(4,5)cyclohepta(1,2-b)tiophen-Derivaten - Google Patents
Verfahren zur Herstellung von neuen 9,10-Dihydro-4H-benzo(4,5)cyclohepta(1,2-b)tiophen-DerivatenInfo
- Publication number
- CH473138A CH473138A CH806165A CH806165A CH473138A CH 473138 A CH473138 A CH 473138A CH 806165 A CH806165 A CH 806165A CH 806165 A CH806165 A CH 806165A CH 473138 A CH473138 A CH 473138A
- Authority
- CH
- Switzerland
- Prior art keywords
- cyclohepta
- dihydro
- benzo
- general formula
- group
- Prior art date
Links
- JWZOUYNYLGHDKZ-UHFFFAOYSA-N 5,10-dihydro-4h-benzo[1,2]cyclohepta[3,4-b]thiophene Chemical class C1CC2=CC=CC=C2CC2=C1SC=C2 JWZOUYNYLGHDKZ-UHFFFAOYSA-N 0.000 title claims description 3
- 238000000034 method Methods 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 9
- -1 chloroformic acid ester Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000002897 diene group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- NFHHBIGYIAIGFH-UHFFFAOYSA-N 2h-cyclohepta[b]thiophene Chemical class C1=CC=CC2=CCSC2=C1 NFHHBIGYIAIGFH-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CHXZRHMQQRUVHF-UHFFFAOYSA-N thiophene A Natural products CC#CC1=CC=C(C#CC#CC=C)S1 CHXZRHMQQRUVHF-UHFFFAOYSA-N 0.000 description 3
- LOGWEKKXJXKVDL-UHFFFAOYSA-N 2-[2-(6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-2-ylidene)ethyl]piperidine Chemical compound N1C(CCCC1)CC=C1C2=C(CCC=3SC=CC31)C=CC=C2 LOGWEKKXJXKVDL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- BXZXOGSYKXTGHD-UHFFFAOYSA-N CNCC(C=C1C2=C(CCC=3SC=CC31)C=CC=C2)C Chemical compound CNCC(C=C1C2=C(CCC=3SC=CC31)C=CC=C2)C BXZXOGSYKXTGHD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-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
- UGAQDEKMIPOWMS-UHFFFAOYSA-N CN1C(CCCC1)CC=C1C2=C(CCC=3SC=CC31)C=CC=C2 Chemical compound CN1C(CCCC1)CC=C1C2=C(CCC=3SC=CC31)C=CC=C2 UGAQDEKMIPOWMS-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010029333 Neurosis Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 208000012545 Psychophysiologic disease Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical class OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 238000002156 mixing Methods 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
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- HPOKESDSMZRZLC-UHFFFAOYSA-N propan-2-one;hydrochloride Chemical compound Cl.CC(C)=O HPOKESDSMZRZLC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3355/65A GB1089483A (en) | 1964-02-04 | 1965-01-26 | Improvements in or relating to 4h-benzo(4,5)cyclohepta (1,2-b) thiophene derivatives |
| OA51413A OA01524A (fr) | 1964-02-04 | 1965-01-28 | Nouveaux composés hétérocycliques dérivant du benzo-cyclocheptathiophène et procédé permettant leur préparation. |
| NL6501154A NL125442C (en]) | 1964-02-04 | 1965-01-29 | |
| DES95277A DE1238040B (de) | 1964-02-04 | 1965-02-01 | Verfahren zur Herstellung von 4H-Benzo [4, 5]-cyclohepta [1, 2-b] thiophenen |
| FI0244/65A FI42216B (en]) | 1964-02-04 | 1965-02-02 | |
| FR4164A FR1441486A (fr) | 1964-02-04 | 1965-02-02 | Nouveaux composés hétérocycliques dérivant du benzo-cyclohepta-thiophène et procédé permettant leur préparation |
| BE659178A BE659178A (en]) | 1964-02-04 | 1965-02-02 | |
| SE1405/65A SE306323B (en]) | 1964-02-04 | 1965-02-03 | |
| IL22905A IL22905A (en) | 1964-02-04 | 1965-02-03 | 4h-benzo-(4,5)-cyclohepta-(1,2-b)-thiophene derivatives and a process for their production |
| BR166936/65A BR6566936D0 (pt) | 1964-02-04 | 1965-02-04 | Processo para fabricacao de novos derivados 4-4-benzo(4,5) ciclo-hepta (1,2- b) tiofenicos |
| FR15304A FR4369M (en]) | 1964-02-04 | 1965-04-30 | |
| CH806165A CH473138A (de) | 1964-02-04 | 1965-06-09 | Verfahren zur Herstellung von neuen 9,10-Dihydro-4H-benzo(4,5)cyclohepta(1,2-b)tiophen-Derivaten |
| BE668052A BE668052A (en]) | 1964-02-04 | 1965-08-09 | |
| NL6510326A NL6510326A (en]) | 1964-02-04 | 1965-08-09 | |
| ES0316309A ES316309A2 (es) | 1965-06-09 | 1965-08-09 | Procedimiento para la produccion de derivados del 4h-benzo(4,5) ciclohepta (1,2-b) tiofeno. |
| FR27925A FR91208E (fr) | 1964-02-04 | 1965-08-10 | Nouveaux composés hétérocycliques dérivant du benzo-cyclohepta-thiophène et procédé permettant leur préparation |
| CH1519165A CH473146A (de) | 1964-02-04 | 1965-11-03 | Verfahren zur Herstellung von neuen 4H-Benzo(4,5)cyclohepta(1,2-b)thiophen-Derivaten |
| GB47266/66A GB1159480A (en) | 1964-02-04 | 1966-10-21 | 4H-Benzo[4,5]Cyclohepta[1,2-b]-Thiophene Derivatives |
| DE19661620420 DE1620420A1 (de) | 1964-02-04 | 1966-10-28 | Neue 4H-Benzo[4,5]cyclohepta[1,2-b]thiophen-Derivate |
| BR184229/66A BR6684229D0 (pt) | 1964-02-04 | 1966-10-31 | Processo de fabricacao de novos derivados do 4h-benzo 4,5 ciclo-hepta 1,2-b tiofeno |
| FR82202A FR92121E (fr) | 1964-02-04 | 1966-11-02 | Nouveaux composés hétérocycliques dérivant du benzo-cycloheptathiophène et procédé permettant leur préparation |
| ES332985A ES332985A2 (es) | 1964-02-04 | 1966-11-02 | Procedimiento para la produccion de derivados de 4 h-ben- zo (4,5) ciclohepta (1,2-b) tiofeno. |
| US642295A US3464983A (en) | 1964-02-04 | 1967-05-31 | 4h-benzo(4,5)cyclohepta(1,2-b)thiophenes |
| US646194A US3491103A (en) | 1963-12-19 | 1967-06-15 | Certain 4h-benzo(4,5)cyclohepta-(1,2-b) thiophenes |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH127564A CH440321A (de) | 1964-02-04 | 1964-02-04 | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen |
| CH1324664 | 1964-10-13 | ||
| CH806165A CH473138A (de) | 1964-02-04 | 1965-06-09 | Verfahren zur Herstellung von neuen 9,10-Dihydro-4H-benzo(4,5)cyclohepta(1,2-b)tiophen-Derivaten |
| CH1519165A CH473146A (de) | 1964-02-04 | 1965-11-03 | Verfahren zur Herstellung von neuen 4H-Benzo(4,5)cyclohepta(1,2-b)thiophen-Derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH473138A true CH473138A (de) | 1969-05-31 |
Family
ID=27428140
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH806165A CH473138A (de) | 1963-12-19 | 1965-06-09 | Verfahren zur Herstellung von neuen 9,10-Dihydro-4H-benzo(4,5)cyclohepta(1,2-b)tiophen-Derivaten |
| CH1519165A CH473146A (de) | 1963-12-19 | 1965-11-03 | Verfahren zur Herstellung von neuen 4H-Benzo(4,5)cyclohepta(1,2-b)thiophen-Derivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1519165A CH473146A (de) | 1963-12-19 | 1965-11-03 | Verfahren zur Herstellung von neuen 4H-Benzo(4,5)cyclohepta(1,2-b)thiophen-Derivaten |
Country Status (12)
| Country | Link |
|---|---|
| BE (2) | BE659178A (en]) |
| BR (2) | BR6566936D0 (en]) |
| CH (2) | CH473138A (en]) |
| DE (2) | DE1238040B (en]) |
| ES (1) | ES332985A2 (en]) |
| FI (1) | FI42216B (en]) |
| FR (4) | FR1441486A (en]) |
| GB (2) | GB1089483A (en]) |
| IL (1) | IL22905A (en]) |
| NL (2) | NL125442C (en]) |
| OA (1) | OA01524A (en]) |
| SE (1) | SE306323B (en]) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU195800B (en) * | 1983-10-13 | 1988-07-28 | Sandoz Ltd | Process for producing 4h-benzo/4,5/cylopenta/1,2-b/ thiofene derivatives and pharmaceutical compositions containing them |
| ATE516804T1 (de) | 1999-09-13 | 2011-08-15 | Bridge Pharma Inc | Optisch aktive isomere von ketotifen und deren therapeutisch wirksame metabolite |
-
1965
- 1965-01-26 GB GB3355/65A patent/GB1089483A/en not_active Expired
- 1965-01-28 OA OA51413A patent/OA01524A/xx unknown
- 1965-01-29 NL NL6501154A patent/NL125442C/xx active
- 1965-02-01 DE DES95277A patent/DE1238040B/de active Pending
- 1965-02-02 FR FR4164A patent/FR1441486A/fr not_active Expired
- 1965-02-02 BE BE659178A patent/BE659178A/xx unknown
- 1965-02-02 FI FI0244/65A patent/FI42216B/fi active
- 1965-02-03 IL IL22905A patent/IL22905A/en unknown
- 1965-02-03 SE SE1405/65A patent/SE306323B/xx unknown
- 1965-02-04 BR BR166936/65A patent/BR6566936D0/pt unknown
- 1965-04-30 FR FR15304A patent/FR4369M/fr not_active Expired
- 1965-06-09 CH CH806165A patent/CH473138A/de unknown
- 1965-08-09 BE BE668052A patent/BE668052A/xx unknown
- 1965-08-09 NL NL6510326A patent/NL6510326A/xx unknown
- 1965-08-10 FR FR27925A patent/FR91208E/fr not_active Expired
- 1965-11-03 CH CH1519165A patent/CH473146A/de unknown
-
1966
- 1966-10-21 GB GB47266/66A patent/GB1159480A/en not_active Expired
- 1966-10-28 DE DE19661620420 patent/DE1620420A1/de active Pending
- 1966-10-31 BR BR184229/66A patent/BR6684229D0/pt unknown
- 1966-11-02 FR FR82202A patent/FR92121E/fr not_active Expired
- 1966-11-02 ES ES332985A patent/ES332985A2/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| OA01524A (fr) | 1969-07-21 |
| DE1238040B (de) | 1967-04-06 |
| NL6501154A (en]) | 1965-08-05 |
| BE668052A (en]) | 1966-02-09 |
| GB1159480A (en) | 1969-07-23 |
| CH473146A (de) | 1969-05-31 |
| GB1089483A (en) | 1967-11-01 |
| IL22905A (en) | 1969-01-29 |
| FR91208E (fr) | 1968-05-03 |
| FI42216B (en]) | 1970-03-02 |
| NL6510326A (en]) | 1966-12-12 |
| SE306323B (en]) | 1968-11-25 |
| BR6684229D0 (pt) | 1973-12-26 |
| FR92121E (fr) | 1968-09-27 |
| FR1441486A (fr) | 1966-06-10 |
| ES332985A2 (es) | 1968-03-16 |
| FR4369M (en]) | 1966-08-22 |
| BE659178A (en]) | 1965-08-02 |
| BR6566936D0 (pt) | 1973-08-14 |
| DE1620420A1 (de) | 1970-03-12 |
| NL125442C (en]) | 1968-06-17 |
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