FR2009386A1 - Octahydro-benz h isoquinolin-6-one antiphlogistic - Google Patents
Octahydro-benz h isoquinolin-6-one antiphlogisticInfo
- Publication number
- FR2009386A1 FR2009386A1 FR6916923A FR6916923A FR2009386A1 FR 2009386 A1 FR2009386 A1 FR 2009386A1 FR 6916923 A FR6916923 A FR 6916923A FR 6916923 A FR6916923 A FR 6916923A FR 2009386 A1 FR2009386 A1 FR 2009386A1
- Authority
- FR
- France
- Prior art keywords
- benzyl
- isoquinolin
- octahydro
- benz
- antiphlogistic
- 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.)
- Withdrawn
Links
- 230000001741 anti-phlogistic effect Effects 0.000 title abstract 2
- GPVPDRHTRGTSIH-UHFFFAOYSA-N isoquinolin-6-ol Chemical compound C1=NC=CC2=CC(O)=CC=C21 GPVPDRHTRGTSIH-UHFFFAOYSA-N 0.000 title abstract 2
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- LUSBTWIASYDYOB-UHFFFAOYSA-N 2,3,4,4a,5,10b-hexahydro-1h-benzo[h]isoquinolin-6-one Chemical compound C12=CC=CC=C2C(=O)CC2C1CNCC2 LUSBTWIASYDYOB-UHFFFAOYSA-N 0.000 abstract 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
(A) 1,2,3,4,4a,5,6,10b-Octahydrobenz(h)isoquinolin-6-one (I) and its acid addition salts (B) Starting materials (II) (see 'Preparation'), and their acid addition salts. (I) has antiphlogistic activity; daily dosage 50-150 mg. By cleaving the residue R from a cpd. of formula (II): (R = benzyl or methyl) This is pref. done by (a) reacting with Cl-COOR1 (R1 = lower alkyl, phenyl or benzyl) and hydrolysing (or, when R1 = benzyl, hydrogenolysing) the resulting 2-(alkoxy-, phenoxy- or benzyloxy-carbonyl)-octahydro-benz(h)isoquinolin-6-one, (b) reacting (II) with BrCN and hydrolysing the resulting cyanamide, or (c) when R is benzyl, removing the benzyl group hydrogenolytically.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH780168A CH504438A (en) | 1968-05-27 | 1968-05-27 | Process for the preparation of 1,2,3,4,4a, 5,6,10b-octahydrobenz (h) isoquinolin-6-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2009386A1 true FR2009386A1 (en) | 1970-02-06 |
Family
ID=4330691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR6916923A Withdrawn FR2009386A1 (en) | 1968-05-27 | 1969-05-23 | Octahydro-benz h isoquinolin-6-one antiphlogistic |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE733658A (en) |
| CH (1) | CH504438A (en) |
| DE (1) | DE1926022A1 (en) |
| FR (1) | FR2009386A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3297058B2 (en) | 1997-01-08 | 2002-07-02 | エフ．ホフマン−ラ ロシュ アーゲー | Tricyclic benzo [e] isoindole and benzo [h] isoquinoline |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4678791A (en) * | 1985-05-07 | 1987-07-07 | Pennwalt Corporation | 6-phenyl-1,2-3,4,4a,5-6,10b-octahydrobenz(h)isoquinolines useful for treating depression |
| ZA9817B (en) * | 1997-01-08 | 1998-07-08 | Hoffmann La Roche | Tricyclic benzo[e]isoindoles and benzo[h]isoquinolines |
-
1968
- 1968-05-27 CH CH780168A patent/CH504438A/en not_active IP Right Cessation
-
1969
- 1969-05-22 DE DE19691926022 patent/DE1926022A1/en active Pending
- 1969-05-23 FR FR6916923A patent/FR2009386A1/en not_active Withdrawn
- 1969-05-27 BE BE733658D patent/BE733658A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NEANT * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3297058B2 (en) | 1997-01-08 | 2002-07-02 | エフ．ホフマン−ラ ロシュ アーゲー | Tricyclic benzo [e] isoindole and benzo [h] isoquinoline |
Also Published As
| Publication number | Publication date |
|---|---|
| BE733658A (en) | 1969-11-27 |
| CH504438A (en) | 1971-03-15 |
| DE1926022A1 (en) | 1969-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |