CH565172A5 - 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors - Google Patents
4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitorsInfo
- Publication number
- CH565172A5 CH565172A5 CH98872A CH98872A CH565172A5 CH 565172 A5 CH565172 A5 CH 565172A5 CH 98872 A CH98872 A CH 98872A CH 98872 A CH98872 A CH 98872A CH 565172 A5 CH565172 A5 CH 565172A5
- Authority
- CH
- Switzerland
- Prior art keywords
- piperidylidene
- cyclohepta
- formula
- benzo
- methyl
- 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
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 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 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000003544 oxime group Chemical group 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- NFHHBIGYIAIGFH-UHFFFAOYSA-N 2h-cyclohepta[b]thiophene Chemical class C1=CC=CC2=CCSC2=C1 NFHHBIGYIAIGFH-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- VKHZVYSAANYDBM-UHFFFAOYSA-N 10-(1-methylpiperidin-4-ylidene)-4h-benzo[1,2]cyclohepta[3,4-b]thiophen-5-one Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C(=O)CC2=C1C=CS2 VKHZVYSAANYDBM-UHFFFAOYSA-N 0.000 claims 1
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 claims 1
- YEEXUKDZXMGPOA-UHFFFAOYSA-N N-[2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-9-ylidene]hydroxylamine Chemical compound ON=C1C2=C(C(C3=C(SC=C3)C1)=C1CCN(CC1)C)C=CC=C2 YEEXUKDZXMGPOA-UHFFFAOYSA-N 0.000 claims 1
- -1 hydroxyimino-methylene Chemical group 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000001558 histaminolytic effect Effects 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 231100000820 toxicity test Toxicity 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 230000001078 anti-cholinergic effect Effects 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
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004452 microanalysis Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MHGBFEJHQLAUQM-UHFFFAOYSA-N 10h-benzo[1,2]cyclohepta[3,4-b]thiophene Chemical class C1=CC2=CC=CC=C2CC2=C1SC=C2 MHGBFEJHQLAUQM-UHFFFAOYSA-N 0.000 description 1
- MPWNQFUEPQCCIS-UHFFFAOYSA-N Cl.S1C=2C(=CC1)C=CC=CC2 Chemical compound Cl.S1C=2C(=CC1)C=CC=CC2 MPWNQFUEPQCCIS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010040108 Serotonin syndrome Diseases 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- MXBFSAYTTZBUBY-UHFFFAOYSA-N n-chlorohydroxylamine Chemical compound ONCl MXBFSAYTTZBUBY-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material 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
-
- 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)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE794377D BE794377A (fr) | 1972-01-24 | Nouveaux derives du benzo-cyclohepta-thiophene | |
| CH98872A CH565172A5 (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 |
| DK22573A DK134405B (da) | 1972-01-24 | 1973-01-15 | Analogifremgangsmåde til fremstilling af benzo/4,5/cyclohepta/1,2-b/thiophenderivater eller syreadditionssalte deraf. |
| 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 |
| PL18205073A PL92124B1 (cs) | 1972-01-24 | 1973-01-22 | |
| PL16037373A PL83920B1 (cs) | 1972-01-24 | 1973-01-22 | |
| GB311873A GB1415591A (en) | 1972-01-24 | 1973-01-22 | Benzocycloheptathiophene derivatives |
| CS415273A CS180000B2 (en) | 1972-01-24 | 1973-01-23 | Method for production of novel benzocycloheptathiophenone derivatives |
| FR7302444A FR2183663B2 (cs) | 1972-01-24 | 1973-01-24 | |
| SU2027852A SU505364A3 (ru) | 1972-01-24 | 1974-05-28 | Способ получени производных 4н-бензо (4,5)ц клогепта (1,2-в) триофена |
| ES438596A ES438596A1 (es) | 1972-01-24 | 1975-06-16 | Procedimiento para la obtencion de derivados de benzociclo- heptatiofeno. |
| AT685775A AT337182B (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 |
| 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 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH98872A CH565172A5 (en) | 1972-01-24 | 1972-01-24 | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH565172A5 true CH565172A5 (en) | 1975-08-15 |
Family
ID=4199855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH98872A CH565172A5 (en) | 1972-01-24 | 1972-01-24 | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH565172A5 (cs) |
| CS (1) | CS180000B2 (cs) |
| DK (1) | DK134405B (cs) |
| ES (1) | ES438596A1 (cs) |
| PL (1) | PL92124B1 (cs) |
| SU (1) | SU505364A3 (cs) |
-
1972
- 1972-01-24 CH CH98872A patent/CH565172A5/de not_active IP Right Cessation
-
1973
- 1973-01-15 DK DK22573A patent/DK134405B/da not_active IP Right Cessation
- 1973-01-22 PL PL18205073A patent/PL92124B1/pl unknown
- 1973-01-23 CS CS415273A patent/CS180000B2/cs unknown
-
1974
- 1974-05-28 SU SU2027852A patent/SU505364A3/ru active
-
1975
- 1975-06-16 ES ES438596A patent/ES438596A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU505364A3 (ru) | 1976-02-28 |
| DK134405C (cs) | 1977-03-28 |
| PL92124B1 (cs) | 1977-03-31 |
| DK134405B (da) | 1976-11-01 |
| ES438596A1 (es) | 1977-09-01 |
| CS180000B2 (en) | 1977-12-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE68908374T2 (de) | Propenonoximether, Verfahren zu dessen Herstellung sowie diese enthaltende Arzneinmittel. | |
| DE2111071A1 (de) | Verfahren zur Herstellung neuer heterocyclischer Verbindungen | |
| EP0528922B1 (de) | Neue sulfonylverbindungen | |
| DE1470157A1 (de) | Verfahren zur Herstellung substituierter Thioxanthensulfonamide und ihrer Saeureanlagerungssalze | |
| DE2302944C2 (de) | 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 | |
| DE1445845A1 (de) | Neue Benzomorphane und Verfahren zu ihrer Herstellung | |
| AT337182B (de) | Verfahren zur herstellung neuer 4-(4-piperidyliden)-4h-benzo(4,5)cyclohepta (1,2-b) thiophen-derivate und ihrer saureadditionssalze | |
| CH565172A5 (en) | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors | |
| CH630903A5 (en) | Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. | |
| EP0301245B1 (de) | 3-Sulfonyl-3,7-diazabicyclo-(3,3,1)nonan-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2331721A1 (de) | Verfahren zur herstellung neuer heterocyclischer verbindungen | |
| DE2903917C2 (cs) | ||
| DE2625641A1 (de) | Neue benzocycloheptathiophenderivate ihre herstellung und verwendung als heilmittel | |
| AT337181B (de) | Verfahren zur herstellung neuer 4-(4-piperidyliden)-4h-benzo(4,5)cyclohepta(1,2-b)thiophen-derivate und ihrer saureadditionssalze | |
| EP0014996B1 (de) | Heterocyclische spiroverknüpfte Amidine, ihre Stereoisomeren und optischen Isomeren, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE1931487C3 (de) | In 5-Stellung substituierte 5,10-Dihydro-11H-dibenzo eckige Klammer auf b,e eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu diazepin-11 -one und Verfahren zu ihrer Herstellung | |
| CH562244A5 (en) | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors | |
| CH511840A (de) | Verfahren zur Herstellung von neuen Indolderivaten | |
| AT251765B (de) | Verfahren zur Herstellung von neuen Yohimbanderivaten und von deren Salzen | |
| CH537404A (de) | Verfahren zur Herstellung neuer Thiophenderivate | |
| CH569006A5 (en) | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors | |
| AT204551B (de) | Verfahren zur Herstellung von neuen Pyrazolon-Derivaten | |
| DE927928C (de) | Verfahren zur Herstellung von 4-substituierten Chinazolonen | |
| CH473138A (de) | Verfahren zur Herstellung von neuen 9,10-Dihydro-4H-benzo(4,5)cyclohepta(1,2-b)tiophen-Derivaten | |
| CH569012A5 (en) | 4-piperidylidene benzocycloheptathiophenes - - antihistamines and serotonin and acetyl choline inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |