GB2016012A - Pharmaceutically active decahydroisoquinoline derivatives - Google Patents
Pharmaceutically active decahydroisoquinoline derivativesInfo
- Publication number
- GB2016012A GB2016012A GB7907868A GB7907868A GB2016012A GB 2016012 A GB2016012 A GB 2016012A GB 7907868 A GB7907868 A GB 7907868A GB 7907868 A GB7907868 A GB 7907868A GB 2016012 A GB2016012 A GB 2016012A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- hydrogen
- alkoxy
- formula
- trifluoromethyl
- 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.)
- Granted
Links
- NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical class C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
Compounds of formula I <IMAGE> wherein R1, R2 and R3 are chosen from (i), (ii) and (iii):- (i) R1 and R2, independently, are hydrogen (C1-6)alkyl, trifluoromethyl, halogen, or (C1-4)alkoxy and R3 is hydrogen, or (ii) (a) R1 and R2, independently, are hydrogen, (C1-6)alkyl, trifluoromethyl or halogen, or (b) R1 is (C1-4)alkoxy and R2 is (C1-6)alkyl, trifluoromethyl, halogen or (C1-4)alkoxy, and R3 is (C1-6)alkyl, a radical of formula II, -CH2.CH = CR4R5 II wherein R4 and R5, independently, are hydrogen or (C1-4)alkyl, a radical of formula III, <IMAGE> wherein m is 2, 3 or 4, a radical of formula IV <IMAGE> wherein n is 1 or 2, or a radical of formula V <IMAGE> wherein p is 1 or 2 and R6 is hydrogen, halogen, trifluoromethyl, (C1-4)alkoxy, (C1-4)alkyl, amino, di[(C1-4)alkyl]amino (C1-4)alkylamino, or (iii) the azido group is cis to the phenyl group, R1 is (C1-4)alkoxy in the meta position, R2 is hydrogen, and R3 is methyl, are useful analgesic agents.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH264378A CH636859A5 (en) | 1978-03-10 | 1978-03-10 | Substituted cis-4a-phenyldecahydroisoquinolines, their preparation and drugs containing them |
| CH628378 | 1978-06-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2016012A true GB2016012A (en) | 1979-09-19 |
| GB2016012B GB2016012B (en) | 1982-07-21 |
Family
ID=25691019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7907868A Expired GB2016012B (en) | 1978-03-10 | 1979-03-06 | Pharmaceutically active decahydro-isoquinoline derivatives |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS54128585A (en) |
| AU (1) | AU529350B2 (en) |
| CA (1) | CA1118775A (en) |
| DE (1) | DE2907461A1 (en) |
| DK (1) | DK88279A (en) |
| ES (1) | ES478430A1 (en) |
| FI (1) | FI790701A7 (en) |
| FR (1) | FR2419286A2 (en) |
| GB (1) | GB2016012B (en) |
| IL (1) | IL56823A0 (en) |
| IT (1) | IT7948220A0 (en) |
| NL (1) | NL7901764A (en) |
| NZ (1) | NZ189856A (en) |
| PH (1) | PH14162A (en) |
| SE (1) | SE7901848L (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015006280A1 (en) * | 2013-07-10 | 2015-01-15 | Vertex Pharmaceuticals Incorporated | Fused piperidine amides as modulators of ion channels |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2600649B1 (en) * | 1986-06-26 | 1989-02-24 | Rhone Poulenc Sante | PROCESS FOR THE PREPARATION OF LEVOMEPROMAZINE ACID MALEATE |
| CN1163487C (en) * | 1995-07-20 | 2004-08-25 | 东丽株式会社 | 4α-Aryl decahydroisoquinoline compound and its medical application |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2655150A1 (en) * | 1975-12-16 | 1977-06-23 | Sandoz Ag | NEW ORGANIC COMPOUNDS, THEIR PRODUCTION AND USE |
-
1979
- 1979-02-26 DE DE19792907461 patent/DE2907461A1/en not_active Withdrawn
- 1979-03-01 DK DK88279A patent/DK88279A/en not_active Application Discontinuation
- 1979-03-01 SE SE7901848A patent/SE7901848L/en not_active Application Discontinuation
- 1979-03-01 FI FI790701A patent/FI790701A7/en not_active Application Discontinuation
- 1979-03-06 GB GB7907868A patent/GB2016012B/en not_active Expired
- 1979-03-06 FR FR7905753A patent/FR2419286A2/en active Granted
- 1979-03-06 IT IT7948220A patent/IT7948220A0/en unknown
- 1979-03-06 NL NL7901764A patent/NL7901764A/en not_active Application Discontinuation
- 1979-03-08 NZ NZ189856A patent/NZ189856A/en unknown
- 1979-03-08 AU AU44956/79A patent/AU529350B2/en not_active Ceased
- 1979-03-08 IL IL56823A patent/IL56823A0/en unknown
- 1979-03-08 CA CA000323128A patent/CA1118775A/en not_active Expired
- 1979-03-08 ES ES478430A patent/ES478430A1/en not_active Expired
- 1979-03-09 PH PH22274A patent/PH14162A/en unknown
- 1979-03-10 JP JP2818379A patent/JPS54128585A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015006280A1 (en) * | 2013-07-10 | 2015-01-15 | Vertex Pharmaceuticals Incorporated | Fused piperidine amides as modulators of ion channels |
| KR20160030983A (en) * | 2013-07-10 | 2016-03-21 | 버텍스 파마슈티칼스 인코포레이티드 | Fused piperidine amides as modulators of ion channels |
| CN105473554A (en) * | 2013-07-10 | 2016-04-06 | 沃泰克斯药物股份有限公司 | Fused piperidine amides as modulators of ion channels |
| JP2016526571A (en) * | 2013-07-10 | 2016-09-05 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Condensed piperidine amides as modulators of ion channels |
| AU2014287471B2 (en) * | 2013-07-10 | 2018-11-08 | Vertex Pharmaceuticals Incorporated | Fused piperidine amides as modulators of ion channels |
| US10233191B2 (en) | 2013-07-10 | 2019-03-19 | Vertex Pharmaceuticals Incorporated | Fused piperidine amides as modulators of ion channels |
| CN105473554B (en) * | 2013-07-10 | 2019-08-13 | 沃泰克斯药物股份有限公司 | Fused piperidinamides as ion channel modulators |
| AU2014287471C1 (en) * | 2013-07-10 | 2019-11-28 | Vertex Pharmaceuticals Incorporated | Fused piperidine amides as modulators of ion channels |
| RU2741810C2 (en) * | 2013-07-10 | 2021-01-28 | Вертекс Фармасьютикалз Инкорпорейтед | Amides of condensed piperidine as modulators of ion channels |
| KR102306951B1 (en) | 2013-07-10 | 2021-10-01 | 버텍스 파마슈티칼스 인코포레이티드 | Fused piperidine amides as modulators of ion channels |
Also Published As
| Publication number | Publication date |
|---|---|
| PH14162A (en) | 1981-03-19 |
| IL56823A0 (en) | 1979-05-31 |
| IT7948220A0 (en) | 1979-03-06 |
| NZ189856A (en) | 1981-12-15 |
| FI790701A7 (en) | 1979-09-11 |
| FR2419286B1 (en) | 1982-03-05 |
| AU529350B2 (en) | 1983-06-02 |
| JPS54128585A (en) | 1979-10-05 |
| DE2907461A1 (en) | 1979-09-20 |
| FR2419286A2 (en) | 1979-10-05 |
| AU4495679A (en) | 1979-09-13 |
| DK88279A (en) | 1979-09-11 |
| NL7901764A (en) | 1979-09-12 |
| CA1118775A (en) | 1982-02-23 |
| ES478430A1 (en) | 1979-05-16 |
| SE7901848L (en) | 1979-09-11 |
| GB2016012B (en) | 1982-07-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |