CH569012A5 - 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors - Google Patents
4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitorsInfo
- Publication number
- CH569012A5 CH569012A5 CH98672A CH98672A CH569012A5 CH 569012 A5 CH569012 A5 CH 569012A5 CH 98672 A CH98672 A CH 98672A CH 98672 A CH98672 A CH 98672A CH 569012 A5 CH569012 A5 CH 569012A5
- Authority
- CH
- Switzerland
- Prior art keywords
- piperidylidene
- benzo
- thiophen
- halogen
- formula
- Prior art date
Links
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 title description 2
- 229960004373 acetylcholine Drugs 0.000 title description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 title 2
- LGPJQAJDEAAABN-UHFFFAOYSA-N 4-(2H-cyclohepta[e][1]benzothiol-3-ylidene)piperidine Chemical class N1CCC(CC1)=S1CC=C2C1=CC=C1C2=CC=CC=C1 LGPJQAJDEAAABN-UHFFFAOYSA-N 0.000 title 1
- 229940125715 antihistaminic agent Drugs 0.000 title 1
- 239000000739 antihistaminic agent Substances 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 229940076279 serotonin Drugs 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 9
- -1 hydroxyimino-methylene Chemical group 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- ZUZJVPBIRPJYMV-UHFFFAOYSA-N 2-(1-benzylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-8-one Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)=C1C2=C(CC(C=3SC=CC31)=O)C=CC=C2 ZUZJVPBIRPJYMV-UHFFFAOYSA-N 0.000 claims 1
- GERPMJPJRJGAGL-UHFFFAOYSA-N C1CN(CCC1=C2C3=C(C(=O)CC4=CC=CC=C42)SC=C3)CC5=CC=C(C=C5)Cl Chemical compound C1CN(CCC1=C2C3=C(C(=O)CC4=CC=CC=C42)SC=C3)CC5=CC=C(C=C5)Cl GERPMJPJRJGAGL-UHFFFAOYSA-N 0.000 claims 1
- IYSYPCSSDZBWHN-UHFFFAOYSA-N Nor-ketotifen Chemical compound C1=2C=CSC=2C(=O)CC2=CC=CC=C2C1=C1CCNCC1 IYSYPCSSDZBWHN-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 231100000820 toxicity test Toxicity 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000004452 microanalysis Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CRPNZWHJMWDQCK-UHFFFAOYSA-N 1-benzyl-4-(6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,8,10,12-hexaen-2-ylidene)piperidine Chemical compound S1C2=C(C=C1)C(C1=C(C=C2)C=CC=C1)=C1CCN(CC1)CC1=CC=CC=C1 CRPNZWHJMWDQCK-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- MHGBFEJHQLAUQM-UHFFFAOYSA-N 10h-benzo[1,2]cyclohepta[3,4-b]thiophene Chemical compound C1=CC2=CC=CC=C2CC2=C1SC=C2 MHGBFEJHQLAUQM-UHFFFAOYSA-N 0.000 description 1
- MMHDAZZFENXBCE-UHFFFAOYSA-N 5,10-dihydrobenzo[1,2]cyclohepta[3,4-b]thiophen-4-one Chemical compound O=C1CC2=CC=CC=C2CC2=C1SC=C2 MMHDAZZFENXBCE-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- RNFJTAXCEVXIFZ-UHFFFAOYSA-N O=C(CC1=C2C=CC(Cl)=C1)C(SC=C1)=C1C2=C1CCNCC1 Chemical compound O=C(CC1=C2C=CC(Cl)=C1)C(SC=C1)=C1C2=C1CCNCC1 RNFJTAXCEVXIFZ-UHFFFAOYSA-N 0.000 description 1
- 206010040108 Serotonin syndrome Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000001558 histaminolytic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012730 sustained-release form Substances 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D409/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D409/08—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 linked by a carbon chain containing alicyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE794377D BE794377A (fr) | 1972-01-24 | Nouveaux derives du benzo-cyclohepta-thiophene | |
| CH98672A CH569012A5 (en) | 1972-01-24 | 1972-01-24 | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors |
| US286281A US3862156A (en) | 1972-01-24 | 1972-09-05 | 4h-benzo{8 4,5{9 cyclohepta{8 1,2-6{9 thiophenes |
| JP47117590A JPS5760351B2 (cs) | 1972-01-24 | 1972-11-22 | |
| DD167577A DD102701A5 (cs) | 1972-01-24 | 1972-12-15 | |
| SE7300501A SE383347B (sv) | 1972-01-24 | 1973-01-15 | Forfarande for framstellning av nya 4 h-benso (4,5)cyklohepta (1,2-b)tiofenderivat |
| FI110/73A FI55843C (fi) | 1972-01-24 | 1973-01-16 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 9,10-dihydro-9- eller -10-hydroxi-imino-4-(1-alkyl-4-piperidyliden)-4h-benso(4,5)cyklohepta(1,2-b)tiofenderivat och deras syraadditionssalter |
| NL7300796A NL7300796A (cs) | 1972-01-24 | 1973-01-19 | |
| CY992A CY992A (en) | 1972-01-24 | 1973-01-22 | Benzocycloheptathiophene derivatives |
| HUSA2447A HU165130B (cs) | 1972-01-24 | 1973-01-22 | |
| DE2302944A DE2302944C2 (de) | 1972-01-24 | 1973-01-22 | 9,10-Dihydro-4-(1-subst.-4-piperidyliden)-4H-benzol [4,5] cyclohepta [1,2-b] thiophene, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| GB311873A GB1415591A (en) | 1972-01-24 | 1973-01-22 | Benzocycloheptathiophene derivatives |
| AU51377/73A AU482530B2 (en) | 1973-01-23 | Benzocycloheptathiophenes | |
| CS7300000504A CS179977B2 (en) | 1972-01-24 | 1973-01-23 | Method for producing novel derivatives of benzocycloheptathiophenone |
| FR7302444A FR2183663B2 (cs) | 1972-01-24 | 1973-01-24 | |
| SU2017993A SU520914A3 (ru) | 1972-01-24 | 1974-04-23 | Способ получени производных бензоциклогептатиофенонов или их солей |
| ES438598A ES438598A1 (es) | 1972-01-24 | 1975-06-16 | Procedimiento para la obtencion de derivados de benzocilo- heptatiofeno. |
| AT685675A AT337181B (de) | 1972-01-24 | 1975-09-05 | Verfahren zur herstellung neuer 4-(4-piperidyliden)-4h-benzo(4,5)cyclohepta(1,2-b)thiophen-derivate und ihrer saureadditionssalze |
| SE7600275A SE423712B (sv) | 1972-01-24 | 1976-01-13 | Forfarande for framstellning av 4-(1-bensyl-4-piperidyliden)-4h-benso-/4.5/cyklohepta/1,2-b/-tiofen-10(9h) /eller 9 (10h) /-on-derivat |
| DK16376A DK16376A (da) | 1972-01-24 | 1976-01-15 | Fremgangsmade til fremstilling af terapeutisk aktive 4h-benzo(4,5)cyclohepta(1,2-b)thiophenderivater |
| FI790145A FI59591C (fi) | 1972-01-24 | 1979-01-17 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4h-benso(4,5)syklohepta(1,2-b)tiofen-derivat |
| HK112/79A HK11279A (en) | 1972-01-24 | 1979-03-08 | Benzocycloheptathiophene derivatives |
| MY114/79A MY7900114A (en) | 1972-01-24 | 1979-12-30 | Benzocycloheptathiophene derivatives |
| JP55175690A JPS5817756B2 (ja) | 1972-01-24 | 1980-12-11 | ４Ｈ−ベンゾ〔４，５〕シクロヘプタ〔１，２−ｂ〕チオフエン誘導体の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH98672A CH569012A5 (en) | 1972-01-24 | 1972-01-24 | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH569012A5 true CH569012A5 (en) | 1975-11-14 |
Family
ID=4199812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH98672A CH569012A5 (en) | 1972-01-24 | 1972-01-24 | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5817756B2 (cs) |
| CH (1) | CH569012A5 (cs) |
| CS (1) | CS179977B2 (cs) |
| ES (1) | ES438598A1 (cs) |
| SE (1) | SE423712B (cs) |
| SU (1) | SU520914A3 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS649343U (cs) * | 1987-07-07 | 1989-01-19 |
-
1972
- 1972-01-24 CH CH98672A patent/CH569012A5/de not_active IP Right Cessation
-
1973
- 1973-01-23 CS CS7300000504A patent/CS179977B2/cs unknown
-
1974
- 1974-04-23 SU SU2017993A patent/SU520914A3/ru active
-
1975
- 1975-06-16 ES ES438598A patent/ES438598A1/es not_active Expired
-
1976
- 1976-01-13 SE SE7600275A patent/SE423712B/xx unknown
-
1980
- 1980-12-11 JP JP55175690A patent/JPS5817756B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE7600275L (sv) | 1976-01-13 |
| SE423712B (sv) | 1982-05-24 |
| JPS5817756B2 (ja) | 1983-04-09 |
| CS179977B2 (en) | 1977-12-30 |
| SU520914A3 (ru) | 1976-07-05 |
| JPS57112390A (en) | 1982-07-13 |
| AU5137773A (en) | 1974-07-25 |
| ES438598A1 (es) | 1977-05-16 |
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