GB1512653A - Indazoles and the like - Google Patents
Indazoles and the likeInfo
- Publication number
- GB1512653A GB1512653A GB1968275A GB1968275A GB1512653A GB 1512653 A GB1512653 A GB 1512653A GB 1968275 A GB1968275 A GB 1968275A GB 1968275 A GB1968275 A GB 1968275A GB 1512653 A GB1512653 A GB 1512653A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- acid addition
- formula
- oxide
- compound
- 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
- 150000002473 indoazoles Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 150000001204 N-oxides Chemical group 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-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 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000003874 central nervous system depressant Substances 0.000 abstract 1
- UREWVVFRSGFOEL-UHFFFAOYSA-N cyclohepta[c]pyrazole Chemical class C1=CC=CC=C2C=NN=C21 UREWVVFRSGFOEL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 229940124531 pharmaceutical excipient Drugs 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1512653 Indazoles and cyclopenta- or cyclohepta-pyrazoles E R SQUIBB & SONS Inc 9 May 1975 [13 May 1974] 19682/75 Heading C2C Novel compounds I in which X is H, halogen, CF 3 , C 1-8 alkyl or C 1-8 alkoxy, m is 2 to 4, R is H or C 1-8 alkyl provided that only one R may be C 1-8 alkyl, A is C 1-8 alkylene and B is NH 2 , NHR<SP>1</SP>, NR<SP>1</SP>R<SP>1</SP> or NR<SP>1</SP>R<SP>2</SP>, where R<SP>1</SP> is C 1-8 alkyl and R<SP>2</SP> is phenyl or phenyl-C 1-8 alkyl, and acid addition salts, quaternary salts, N-oxides and N-oxide acid addition salts thereof, are prepared by reacting a compound IV with a hydrazine of formula or a hydroxyalkylhydrazine of formula and, when the hydroxyalkylhydrazine is used, heating the resulting alcohol with p-toluenesulphonyl chloride and then with an amine of formula HB, followed, if desired, by converting a resulting compound I into an acid addition or quaternary salt, N-oxide or acid addition salt of an N-oxide. Compounds IV are prepared by reacting an appropriate benzaldehyde with an appropriate cycloalkanone. Pharmaceutical compositions useful as CNS depressants and in a form suitable for oral or parenteral administration comprise a compound of the invention together with a pharmaceutical excipient.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46917174A | 1974-05-13 | 1974-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1512653A true GB1512653A (en) | 1978-06-01 |
Family
ID=23862720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1968275A Expired GB1512653A (en) | 1974-05-13 | 1975-05-09 | Indazoles and the like |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS50160271A (en) |
| CA (1) | CA1065324A (en) |
| DE (1) | DE2521299A1 (en) |
| FR (1) | FR2270871B1 (en) |
| GB (1) | GB1512653A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4004007A (en) * | 1975-08-08 | 1977-01-18 | E. R. Squibb & Sons, Inc. | 2-Heterocyclicalkyl-3,3a,4,5,6,7-hexahydro-3-phenyl-7-(phenylmethylene)-2H-indazoles |
| ID17907A (en) * | 1997-02-20 | 1998-02-05 | Fakultas Farmasi Uni Gajah Mad | BENZILIDIN CYCYLOHEXANON BENZILIDINE CYCOPOPANANONE BINZYLIDINE ACETONE AND ITS PRODUCTION |
| RU2009148866A (en) | 2007-06-01 | 2011-07-20 | Шеринг Корпорейшн (US) | GAMMA SECRETASE MODULATORS |
| US8809318B2 (en) * | 2008-11-13 | 2014-08-19 | Merck Sharp & Dohme Corp. | Gamma secretase modulators |
-
1975
- 1975-05-02 CA CA226,132A patent/CA1065324A/en not_active Expired
- 1975-05-09 GB GB1968275A patent/GB1512653A/en not_active Expired
- 1975-05-13 JP JP5788275A patent/JPS50160271A/ja active Pending
- 1975-05-13 DE DE19752521299 patent/DE2521299A1/en not_active Ceased
- 1975-05-13 FR FR7514896A patent/FR2270871B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50160271A (en) | 1975-12-25 |
| CA1065324A (en) | 1979-10-30 |
| FR2270871A1 (en) | 1975-12-12 |
| DE2521299A1 (en) | 1975-11-27 |
| FR2270871B1 (en) | 1978-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |