GB1210106A - Derivatives of 1,2,3,4-tetrahydrobenzothieno [2,3-c]pyridine and of 1,2,3,4-tetrahydro-5h-benzothieno[2,3-c]azepine - Google Patents
Derivatives of 1,2,3,4-tetrahydrobenzothieno [2,3-c]pyridine and of 1,2,3,4-tetrahydro-5h-benzothieno[2,3-c]azepineInfo
- Publication number
- GB1210106A GB1210106A GB00892/68A GB1089268A GB1210106A GB 1210106 A GB1210106 A GB 1210106A GB 00892/68 A GB00892/68 A GB 00892/68A GB 1089268 A GB1089268 A GB 1089268A GB 1210106 A GB1210106 A GB 1210106A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- general formula
- pyridine
- group
- treatment
- 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
- LOSHLRVJQKCQNH-UHFFFAOYSA-N 1,2,3,4-tetrahydro-[1]benzothiolo[2,3-c]pyridine Chemical class S1C2=CC=CC=C2C2=C1CNCC2 LOSHLRVJQKCQNH-UHFFFAOYSA-N 0.000 title abstract 4
- ZXQRPVDCQJPZFW-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-[1]benzothiolo[2,3-c]azepine Chemical compound C1CCNCC2=C1C1=CC=CC=C1S2 ZXQRPVDCQJPZFW-UHFFFAOYSA-N 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 8
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- -1 morpholino, pyrrolidino, piperidino Chemical group 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 125000005936 piperidyl group Chemical group 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- OSALWPXUDGLMCK-UHFFFAOYSA-N 4,5-dihydro-3H-[1]benzothiolo[2,3-c]azepine Chemical class C1=NCCCC2=C1SC1=C2C=CC=C1 OSALWPXUDGLMCK-UHFFFAOYSA-N 0.000 abstract 1
- 101150071146 COX2 gene Proteins 0.000 abstract 1
- 101100114534 Caenorhabditis elegans ctc-2 gene Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 101150000187 PTGS2 gene Proteins 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000002269 analeptic agent Substances 0.000 abstract 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- 230000000561 anti-psychotic effect Effects 0.000 abstract 1
- 150000001538 azepines Chemical class 0.000 abstract 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,210,106. 1,2,3,4-Tetrahydrobenzothieno[2,3- c]pyridine and 1,2,3,4 - tetrahydro - 5H - benzothiene[2,3-c]azepine derivatives. COLGATEPALMOLIVE CO. 6 March, 1968 [8 March, 1967 (2); 6 Feb., 1968 (2)], No. 10892/68. Heading C2C. Novel 1,2,3,4 - tetrahydrobenzothieno[2,3 - c] pyridine and 1,2,3,4 - tetrahydro - 5H - benzothieno[2,3-c]azepine derivatives of the general formula wherein A and A 1 are the same or different and are hydrogen or halogen atoms or hydroxy, nitro, C 1-4 alkyl, C 1-3 alkoxy or trifluoromethyl groups; m is 1 or 2; R is a hydrogen atom or a C 1-4 alkyl, C 7-11 aralkyl, -(CH 2 ) n OH (in which n is from 2 to 6), B-Am, -COOR 1 , -COBAm or amidino group, in which B is a single chemical bond or a C 1-6 alkylene group; R 1 is a C 1-4 alkyl, di-(C 1-4 alkyl)amino-C 1-4 alkyl, hydroxy- C 1-4 alkyl, C 3-6 alkenyl, C 7-11 aralkyl, C 3-7 cycloalkyl or C 3-7 cycloalkyl-C 1-4 alkyl group; and Am is (a) -NR 2 R 3 in which R 2 and R 3 are the same or different and are hydrogen atoms or C 1-4 alkyl, di-(C 1-4 alkyl)-amino-C 1-4 alkyl, hydroxy-C 1-4 alkyl, C 3-6 alkenyl, C 3-7 cycloalkyl or C 3-7 cycloalkyl-C 1-4 alkyl groups; (b) a morpholino, pyrrolidino, piperidino, N-C 1-4 alkyl - piperazino, N - (phenyl - C 1-4 alkyl). piperazino or N-(hydroxy C 1-4 alkyl)-piperazino group; or (c) a piperidyl or pyrrolidyl radical bonded through a nuclear carbon atom to B; and X 1 and X 2 are the same or different and are hydrogen atoms or C 1-4 alkyl, phenyl, halo- or alkoxy-substituted phenyl, C 7-11 aralkyl, piperidyl, pyridyl, furyl, pyrryl, pyrrolidyl or B-Am groups, provided that X 2 is not a hydrogen atom when X 1 and R are both hydrogen atoms; and pharmaceutically acceptable acid addition and quaternary ammonium salts thereof are prepared, for example, (a) when R is a hydrogen atom and X 1 is a C 1-4 alkyl group, by treatment of a 3-thianaphthenyl-alkylamine of the general formula with an aldehyde or ketone of the general formula X 1 COX 2 in the presence of p-toluenesulphonic acid and toluene, followed by treatment with an acid; (b) when R and X 1 are hydrogen atoms, by reduction of a 3,4-dihydrothianaphtheno[2,3-c]pyridine or 3,4-dihydro- 5H - benzothieno[2,3 - c] - azepine derivative of the general formula and (c) when R is a C 1-4 alkyl or C 7-11 aralkyl group, by treatment of a compound of the first general formula above wherein R is a hydrogen atom with a compound of the general formula RX in which R is a C 1-4 alkyl or C 7-11 aralkyl group and X is a halogen atom, followed optionally by conversion of the product to a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof. Pharmaceutical compositions having antipsychotic, anti - hypertensive and central nervous system stimulant activity comprise, as active ingredient, a 1,2,3,4-tetrahydrobenzothieno[2,3-c]pyridine or 1,2,3,4-tetrahydro-5H- benzothieno[2,3-c]azepine derivative of the first general formula above or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof, and a pharmaceutically acceptable carrier. 1 - Methyl - 3,4 - dihydrothianaphtheno[2,3-c]- pyridine is prepared by reduction of 3-cyanomethylthianaphthene with lithium aluminium hydride, treatment of the resulting #-(3-thianaphthenyl) - ethylamine with acetic anhydride and treatment of the N-[13-(3-thianaphtenyl)- ethyl]acetamide so obtained with phosphorus oxychloride and phosphorus pentoxide.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62143767A | 1967-03-08 | 1967-03-08 | |
| US62147567A | 1967-03-08 | 1967-03-08 | |
| US70590968A | 1968-02-16 | 1968-02-16 | |
| US70589268A | 1968-02-16 | 1968-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1210106A true GB1210106A (en) | 1970-10-28 |
Family
ID=27505164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB00892/68A Expired GB1210106A (en) | 1967-03-08 | 1968-03-06 | Derivatives of 1,2,3,4-tetrahydrobenzothieno [2,3-c]pyridine and of 1,2,3,4-tetrahydro-5h-benzothieno[2,3-c]azepine |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE711887A (en) |
| FR (1) | FR7366M (en) |
| GB (1) | GB1210106A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK152130B (en) * | 1977-06-02 | 1988-02-01 | Parcor | PROCEDURE FOR PREPARING BENZOOEBAATHIENOPYRIDINE DERIVATIVES |
| EP0285671A1 (en) * | 1986-10-13 | 1988-10-12 | Asahi Kasei Kabushiki Kaisha | Pyridine derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3518278A (en) * | 1969-03-20 | 1970-06-30 | Colgate Palmolive Co | Substituted-1,2,3,4-tetrahydrobenzothieno 2,3-pyridine |
-
1968
- 1968-03-06 GB GB00892/68A patent/GB1210106A/en not_active Expired
- 1968-03-08 FR FR142907A patent/FR7366M/fr not_active Expired
- 1968-03-08 BE BE711887D patent/BE711887A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK152130B (en) * | 1977-06-02 | 1988-02-01 | Parcor | PROCEDURE FOR PREPARING BENZOOEBAATHIENOPYRIDINE DERIVATIVES |
| EP0285671A1 (en) * | 1986-10-13 | 1988-10-12 | Asahi Kasei Kabushiki Kaisha | Pyridine derivatives |
| EP0285671A4 (en) * | 1986-10-13 | 1989-06-14 | Asahi Chemical Ind | Pyridine derivatives |
| US5126448A (en) * | 1986-10-13 | 1992-06-30 | Asahi Kasei Kogyo K.K. | Pyridine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR7366M (en) | 1969-10-20 |
| BE711887A (en) | 1968-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLE | Entries relating assignments, transmissions, licences in the register of patents | ||
| PCNP | Patent ceased through non-payment of renewal fee |