GB1225664A - - Google Patents
Info
- Publication number
- GB1225664A GB1225664A GB1225664DA GB1225664A GB 1225664 A GB1225664 A GB 1225664A GB 1225664D A GB1225664D A GB 1225664DA GB 1225664 A GB1225664 A GB 1225664A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lower alkyl
- phenyl
- tetrahydrocarbazole
- alkyl
- methyl
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 14
- -1 morpholino, thiomorpholino, piperidino, pyrrolidino, piperazino Chemical group 0.000 abstract 4
- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 abstract 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- XAMBIJWZVIZZOG-UHFFFAOYSA-N (4-methylphenyl)hydrazine Chemical compound CC1=CC=C(NN)C=C1 XAMBIJWZVIZZOG-UHFFFAOYSA-N 0.000 abstract 1
- VFICJPDIBDJAGL-UHFFFAOYSA-N (4-oxocyclohexyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCC(=O)CC1 VFICJPDIBDJAGL-UHFFFAOYSA-N 0.000 abstract 1
- BGQFJCXLDVNMHY-UHFFFAOYSA-N (6-methyl-2,3,4,9-tetrahydro-1h-carbazol-3-yl) benzoate Chemical compound C1C=2C3=CC(C)=CC=C3NC=2CCC1OC(=O)C1=CC=CC=C1 BGQFJCXLDVNMHY-UHFFFAOYSA-N 0.000 abstract 1
- NAAUMGYTPUOXLM-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazol-3-yl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1CC(C2=CC=CC=C2N2)=C2CC1 NAAUMGYTPUOXLM-UHFFFAOYSA-N 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- NYGMSRICXRZYIQ-UHFFFAOYSA-N 3-(4-phenylpiperazin-1-yl)-2,3,4,9-tetrahydro-1h-carbazole Chemical compound C1CC=2NC3=CC=CC=C3C=2CC1N(CC1)CCN1C1=CC=CC=C1 NYGMSRICXRZYIQ-UHFFFAOYSA-N 0.000 abstract 1
- LOEZCSXETJMUNC-UHFFFAOYSA-N 3-pyrrolidin-1-yl-2,3,4,9-tetrahydro-1h-carbazole Chemical compound C1CCCN1C1CC(C2=CC=CC=C2N2)=C2CC1 LOEZCSXETJMUNC-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000001387 anti-histamine Effects 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000506 psychotropic effect Effects 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
Classifications
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65960667A | 1967-08-10 | 1967-08-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1225664A true GB1225664A (enExample) | 1971-03-17 |
Family
ID=24646046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1225664D Expired GB1225664A (enExample) | 1967-08-10 | 1968-04-10 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3642816A (enExample) |
| JP (3) | JPS509797B1 (enExample) |
| BE (1) | BE714439A (enExample) |
| CH (1) | CH507945A (enExample) |
| DE (1) | DE1770303A1 (enExample) |
| FR (1) | FR7693M (enExample) |
| GB (1) | GB1225664A (enExample) |
| NL (1) | NL6806044A (enExample) |
| SE (1) | SE355018B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3920694A (en) * | 1974-06-03 | 1975-11-18 | Warner Lambert Co | 4-hydroxy-9-methyl-4-vinyl-1,2,3,4-tetrahydrocarbazole |
| EP0603432A1 (en) * | 1992-12-18 | 1994-06-29 | Smithkline Beecham Plc | Tetrahydrocarbazole derivatives for the manufacture of a medicament for the treatment of a disease where a 5-HT1-like agonist is indicated |
| EP0749962A1 (en) * | 1995-06-23 | 1996-12-27 | Eli Lilly And Company | 6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta(7,6-B)indoles |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4224335A (en) * | 1967-08-10 | 1980-09-23 | Sterling Drug Inc. | Tetrahydrocarbazoles and their use |
| US3959309A (en) * | 1968-01-24 | 1976-05-25 | Sterling Drug Inc. | 3-Amido-1,2,3,4-tetrahydrocarbazoles |
| US4062864A (en) * | 1968-01-24 | 1977-12-13 | Sterling Drug Inc. | 3-Hydroxy carbazole derivatives |
| GB1260768A (en) * | 1969-08-28 | 1972-01-19 | Pfizer | N-alkyl-tetrahydrocarbazoles |
| US4257952A (en) * | 1977-06-06 | 1981-03-24 | Sterling Drug Inc. | 3-Amino-tetrahydrocarbazoles |
| US4254134A (en) * | 1978-03-17 | 1981-03-03 | Endo Laboratories, Inc. | Antidepressant 2-amino- and -2-(substituted amino)-cis-hexahydro-carbazoles |
| DE3631824A1 (de) * | 1986-02-21 | 1988-03-31 | Bayer Ag | Cycloalkano(1.2-b)indol-sulfonamide |
| GB9113802D0 (en) * | 1991-06-26 | 1991-08-14 | Smithkline Beecham Plc | Medicaments |
| US5708187A (en) * | 1996-06-27 | 1998-01-13 | Eli Lilly And Company | 6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta 7,6-B!indoles: New 5-HT1F agonists |
-
1967
- 1967-08-10 US US659606A patent/US3642816A/en not_active Expired - Lifetime
-
1968
- 1968-04-10 GB GB1225664D patent/GB1225664A/en not_active Expired
- 1968-04-23 JP JP43026859A patent/JPS509797B1/ja active Pending
- 1968-04-24 CH CH603368A patent/CH507945A/de not_active IP Right Cessation
- 1968-04-29 FR FR149924A patent/FR7693M/fr not_active Expired
- 1968-04-29 NL NL6806044A patent/NL6806044A/xx unknown
- 1968-04-30 BE BE714439D patent/BE714439A/xx unknown
- 1968-04-30 SE SE05885/68A patent/SE355018B/xx unknown
- 1968-04-30 DE DE19681770303 patent/DE1770303A1/de active Pending
-
1974
- 1974-08-28 JP JP9882174A patent/JPS5328915B1/ja active Pending
- 1974-08-28 JP JP49098822A patent/JPS5235669B1/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3920694A (en) * | 1974-06-03 | 1975-11-18 | Warner Lambert Co | 4-hydroxy-9-methyl-4-vinyl-1,2,3,4-tetrahydrocarbazole |
| EP0603432A1 (en) * | 1992-12-18 | 1994-06-29 | Smithkline Beecham Plc | Tetrahydrocarbazole derivatives for the manufacture of a medicament for the treatment of a disease where a 5-HT1-like agonist is indicated |
| EP0749962A1 (en) * | 1995-06-23 | 1996-12-27 | Eli Lilly And Company | 6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta(7,6-B)indoles |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1770303A1 (de) | 1971-10-07 |
| US3642816A (en) | 1972-02-15 |
| CH507945A (de) | 1971-05-31 |
| JPS5235669B1 (enExample) | 1977-09-10 |
| BE714439A (enExample) | 1968-10-30 |
| SE355018B (enExample) | 1973-04-02 |
| JPS509797B1 (enExample) | 1975-04-16 |
| NL6806044A (enExample) | 1969-02-12 |
| JPS5328915B1 (enExample) | 1978-08-17 |
| FR7693M (enExample) | 1970-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |