FR2320098A1 - Pyridylimino or quinolylimino-tetrahydro-thiazolo-isoquinoline cpds. - are analgesics and antipyretics with some antiinflammatory activity - Google Patents
Pyridylimino or quinolylimino-tetrahydro-thiazolo-isoquinoline cpds. - are analgesics and antipyretics with some antiinflammatory activityInfo
- Publication number
- FR2320098A1 FR2320098A1 FR7524523A FR7524523A FR2320098A1 FR 2320098 A1 FR2320098 A1 FR 2320098A1 FR 7524523 A FR7524523 A FR 7524523A FR 7524523 A FR7524523 A FR 7524523A FR 2320098 A1 FR2320098 A1 FR 2320098A1
- Authority
- FR
- France
- Prior art keywords
- pyridyl
- cpds
- thiazolo
- tetrahydro
- antipyretics
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed 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
- C07D217/12—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Thiazolo (3,4-b) isoquinolines of formula (I) as the racemate or isomers and their acid addition salts are novel cpds. (where A = 3-pyridyl, 4-pyridyl or 5-isoquinolyl; when A = 3-pyridyl then X1 = H, halo, dimethylamino or cyano, X2 = H or F and X3 = H or nitro at least two of X1, X2 and X3 = H or X1 and X2 together = methylene -dioxy and X3 = H; when A = 4-pyridyl or 5-isoquinolyl then X1, X2, X3 = H). Cpds. are analgesics and antipyretics with some anti-inflammatory activity. They have low toxicity (LD50 300 to 3000 mg/kg). They may be administered orally, parenterally or rectally in daily doses of 50-1000 mg for adults, e.g. in treatment of chronic or acute pain, rheumatism, dental pain, neurological pain or visceral pain. (I) include 3-(3-pyridyl-imino)-1,5,10,10a-tetrahydrothiazolo (3,4-b) isoquinoline and 3-(5-isoquinolylimino)-1,5,10,10a-tetrahydro-thiazolo (3,4-b) isoquinolines. Cpds. are prepd. by cyclisation of 3 hydroxymethyl-N-(A)-tetrahydro isoquinolylcarbothioamides or by reaction of A-NH2 with 3-chloro-, alkylthio or benzylthio-tetrahydrothiazolo (3,4-b) isoquinolinium salts.
Priority Applications (39)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7524523A FR2320098A1 (en) | 1975-08-06 | 1975-08-06 | Pyridylimino or quinolylimino-tetrahydro-thiazolo-isoquinoline cpds. - are analgesics and antipyretics with some antiinflammatory activity |
NLAANVRAGE7608444,A NL169076C (en) | 1975-08-06 | 1976-07-29 | METHOD FOR PREPARING OR MANUFACTURING PHARMACOLOGICAL PREPARATIONS WITH ANALGETIC AND ANTIPYRETIC ACTION, AND METHOD FOR PREPARING MEDICINAL COMPOUNDS, SUITABLE FOR USE IN SUCH PREPARATIONS |
OA55901A OA05403A (en) | 1975-08-06 | 1976-07-29 | New thiazolo [3,4-b] isoquinoline derivatives and their preparation process. |
GB32128/76A GB1503091A (en) | 1975-08-06 | 1976-08-02 | Thiazolo(3,4-b)isoquinoline derivatives |
CS765082A CS197276B2 (en) | 1975-08-06 | 1976-08-03 | Method of producing new 1,5,10,10a-tetrahydrothiazolo/3,4-b/isoquinolines |
CA258,441A CA1073909A (en) | 1975-08-06 | 1976-08-04 | Thiazolo (3,4-b)-isoquinoleine derivatives preparation and compositions thereof________________________________________________________________ |
IL50208A IL50208A (en) | 1975-08-06 | 1976-08-04 | 3-substituted imino 1,5,10,10a-tetrahydro-thiazolo(3,4-b)isoquinoline derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
LU75540A LU75540A1 (en) | 1975-08-06 | 1976-08-05 | |
DK353876AA DK141069B (en) | 1975-08-06 | 1976-08-05 | Analogous process for preparing 1,5,10,10a-tetrahydrothiazolo (3,4-b) isoquinoline derivatives or acid addition salts thereof. |
US05/711,963 US4064247A (en) | 1975-08-06 | 1976-08-05 | Thiazolo[3,4-b]isoquinoline derivatives and pharmaceutical compositions containing them |
PT65442A PT65442B (en) | 1975-08-06 | 1976-08-05 | NOVEL THIAZOLO / 3,4-B / ISOQUINOLEINE DERIVATIVES FOR THEIR PREPARATION AND COMPOSITIONS CONTAINING THEM |
NZ181693A NZ181693A (en) | 1975-08-06 | 1976-08-05 | 3-heterocyclylimino-1,5,10,10a-tetrahydro thiazolo (3,4-b)isoquinolines |
AU16615/76A AU505316B2 (en) | 1975-08-06 | 1976-08-05 | Thiazolo[3, 4-b]isoquinoline derivatives |
MX762133U MX3639E (en) | 1975-08-06 | 1976-08-05 | PROCEDURE FOR THE PREPARATION OF A DERIVATIVE OF 1,5,10,10A-TETRAHYDRO (3,4-B) TIAZOLO ISOQUINOLEINA |
JP51093548A JPS5219699A (en) | 1975-08-06 | 1976-08-05 | Thiazolo *3*44b* isoquinoline derivative |
SE7608808A SE422065B (en) | 1975-08-06 | 1976-08-05 | PROCEDURE FOR PREPARING NEW DERIVATIVES OF TIAZOLO- (3,4-B) -ISOKINOLINE |
ZA764724A ZA764724B (en) | 1975-08-06 | 1976-08-05 | Thiazolo(3,4-b)isoquinoline derivatives |
NO762729A NO762729L (en) | 1975-08-06 | 1976-08-05 | |
HU76RO00000892A HU173003B (en) | 1975-08-06 | 1976-08-05 | Process for producing new thiasolo-bracket-3,4-b-bracket slosed-isoquinolines |
AR264233A AR211868A1 (en) | 1975-08-06 | 1976-08-05 | PROCEDURE TO OBTAIN NEW DERIVATIVES OF TETRAHYDRO-1,5,10A THIAZOL 3,4-B ISOQUINOLINE |
CH1004176A CH612682A5 (en) | 1975-08-06 | 1976-08-05 | |
IE1728/76A IE44379B1 (en) | 1975-08-06 | 1976-08-05 | Thiazolo (3,4-b)isoquinoline derivatives |
BE169597A BE844927A (en) | 1975-08-06 | 1976-08-05 | NEW THIAZOLO (3,4-b) ISOQUINOLEINE DERIVATIVES, THEIR PREPARATION AND THE COMPOSITIONS CONTAINING THEM |
SU762386213A SU629881A3 (en) | 1975-08-06 | 1976-08-06 | Method of obtaining thiazole (3,4-b) isoquinoline derivatives or their optical isomers or salts |
ES450530A ES450530A1 (en) | 1975-08-06 | 1976-08-06 | Thiazolo{8 3,4-b{9 isoquinoline derivatives and pharmaceutical compositions containing them |
DE2635516A DE2635516C3 (en) | 1975-08-06 | 1976-08-06 | New derivatives of thiazolo [3,4-b] isoquinoline, their preparation and the compositions containing them |
PL1976211043A PL108413B1 (en) | 1975-08-06 | 1976-08-06 | Method of producing new thiazolo/3,4-b/isoquinoline derivatives |
AT586476A AT350054B (en) | 1975-08-06 | 1976-08-06 | PROCESS FOR THE PREPARATION OF NEW 1,5,10,10A-TETRAHYDROTHIAZOLO- (3,4-B) -ISOCHINOLINE- DERIVATIVES AND THEIR ACID ADDITION SALTS |
PL1976191674A PL108034B1 (en) | 1975-08-06 | 1976-08-06 | METHOD OF MAKING NEW TIAZOLO DERIVATIVES / 3,4-BMETHOD OF PRODUCING NEW DERIVATIVES OF THIAZOLO / 3,4-B / ISOQUINOLINE / IZOCHINOLINE |
FI762256A FI60214C (en) | 1975-08-06 | 1976-08-06 | FREQUENCY REFRIGERATION OF NY 5,10,10A-TETRAHYDROTIAZOLO (3,4-B) ISOKINOLINER WITH ANALYTICAL AND ANTIPYRETICAL NETWORK |
PL1976211042A PL108047B1 (en) | 1975-08-06 | 1976-08-06 | METHOD OF MANUFACTURING A NEW DERIVATIVE 1,5,10,10A-CZTEMETHOD OF PRODUCING NEW DERIVATIVE OF 1,5,10,10A-TRIVOHYDROTHIAZOLO / 3,4-B / -ISOCHINOLINE ETRAHYDROTHIAZOLO / 3,4-B / -ISOQUINOLINE |
ES452987A ES452987A1 (en) | 1975-08-06 | 1976-11-04 | Thiazolo{8 3,4-b{9 isoquinoline derivatives and pharmaceutical compositions containing them |
AR267010A AR211170A1 (en) | 1975-08-06 | 1977-03-28 | PROCEDURE FOR THE PREPARATION OF NEW DERIVATIVES OF TETRAHIDRO-1, 5 10, 10A THIAZOL (3, 4-B) ISOQUINOLEIN. |
AR267011A AR219072A1 (en) | 1975-08-06 | 1977-05-28 | PROCEDURE FOR PREPARING NEW DERIVATIVES OF (PIRIDIL-3-IMINO) -3-TETRAHYDRO 1,5,10,10A-THIAZOL (3,4-B) -ISOQUINOLEIN |
SU772504520A SU635874A3 (en) | 1975-08-06 | 1977-07-26 | Method of obtaining 1,5,10,10a-tetra-hydrothiazole/3,4-b/ isoquinoline derivatives or their optical isomers or their acid additive salts |
CS776704A CS197277B2 (en) | 1975-08-06 | 1977-10-14 | Method of producing new 1,5,10,10a-tetrahydrothiazolo/3,4-b/isoquinolines |
CS778474A CS197278B2 (en) | 1975-08-06 | 1977-10-14 | Method of producing derivatives of 1,5,10,10a-tetrahydrothiazolo/3,4-b/isoquinoline |
SU782566502A SU682133A3 (en) | 1975-08-06 | 1978-01-11 | Method of the preparation of tetrahydro-1,5,10,10a thiazolo(3,4-b)isoquinoline derivatives, isomers thereof, a mixture of isomers or their salts |
AT397778A AT351544B (en) | 1975-08-06 | 1978-06-01 | PROCESS FOR THE PREPARATION OF NEW 1,5,10,10A-TETRAHYDROTHIAZOLO- (3,4-B) -ISOCHINOLINE DERIVATIVES AND THEIR ACID ADDITON SALTS |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7524523A FR2320098A1 (en) | 1975-08-06 | 1975-08-06 | Pyridylimino or quinolylimino-tetrahydro-thiazolo-isoquinoline cpds. - are analgesics and antipyretics with some antiinflammatory activity |
Publications (2)
Publication Number | Publication Date |
---|---|
FR2320098A1 true FR2320098A1 (en) | 1977-03-04 |
FR2320098B1 FR2320098B1 (en) | 1978-07-28 |
Family
ID=9158829
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FR7524523A Granted FR2320098A1 (en) | 1975-08-06 | 1975-08-06 | Pyridylimino or quinolylimino-tetrahydro-thiazolo-isoquinoline cpds. - are analgesics and antipyretics with some antiinflammatory activity |
Country Status (6)
Country | Link |
---|---|
AR (1) | AR219072A1 (en) |
BE (1) | BE844927A (en) |
FR (1) | FR2320098A1 (en) |
PL (1) | PL108047B1 (en) |
SU (1) | SU682133A3 (en) |
ZA (1) | ZA764724B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0030198A1 (en) * | 1979-12-04 | 1981-06-10 | Rhone-Poulenc Sante | Isoquinoline derivatives, their preparation and pharmaceutical compositions containing them |
FR2470772A1 (en) * | 1979-12-04 | 1981-06-12 | Rhone Poulenc Ind | 3-Substd. imino 1,5,10,10a-tetra:hydro thiazolo(3,4-b)-isoquinoline - antiviral esp. for rhino viruses some of which have analgesic, antiinflammatory and antipyretic activity |
FR2492379A2 (en) * | 1980-10-17 | 1982-04-23 | Rhone Poulenc Ind | 3-Substd. imino 1,5,10,10a-tetra:hydro thiazolo(3,4-b)-isoquinoline - antiviral esp. for rhino viruses some of which have analgesic, antiinflammatory and antipyretic activity |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4108999A (en) | 1977-02-22 | 1978-08-22 | Rhone-Poulenc Industries | Thiazolo[3,4-b]isoquinoline derivatives, pharmaceutical compositions containing them and pharmaceutical methods using them |
-
1975
- 1975-08-06 FR FR7524523A patent/FR2320098A1/en active Granted
-
1976
- 1976-08-05 BE BE169597A patent/BE844927A/en not_active IP Right Cessation
- 1976-08-05 ZA ZA764724A patent/ZA764724B/en unknown
- 1976-08-06 PL PL1976211042A patent/PL108047B1/en unknown
-
1977
- 1977-05-28 AR AR267011A patent/AR219072A1/en active
-
1978
- 1978-01-11 SU SU782566502A patent/SU682133A3/en active
Non-Patent Citations (1)
Title |
---|
NEANT * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0030198A1 (en) * | 1979-12-04 | 1981-06-10 | Rhone-Poulenc Sante | Isoquinoline derivatives, their preparation and pharmaceutical compositions containing them |
FR2470772A1 (en) * | 1979-12-04 | 1981-06-12 | Rhone Poulenc Ind | 3-Substd. imino 1,5,10,10a-tetra:hydro thiazolo(3,4-b)-isoquinoline - antiviral esp. for rhino viruses some of which have analgesic, antiinflammatory and antipyretic activity |
FR2492379A2 (en) * | 1980-10-17 | 1982-04-23 | Rhone Poulenc Ind | 3-Substd. imino 1,5,10,10a-tetra:hydro thiazolo(3,4-b)-isoquinoline - antiviral esp. for rhino viruses some of which have analgesic, antiinflammatory and antipyretic activity |
Also Published As
Publication number | Publication date |
---|---|
AR219072A1 (en) | 1980-07-31 |
SU682133A3 (en) | 1979-08-25 |
PL108047B1 (en) | 1980-03-31 |
ZA764724B (en) | 1977-07-27 |
BE844927A (en) | 1977-02-07 |
FR2320098B1 (en) | 1978-07-28 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |