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FR2351655A1 - 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 activity

Info

Publication number
FR2351655A1
FR2351655A1 FR7614935A FR7614935A FR2351655A1 FR 2351655 A1 FR2351655 A1 FR 2351655A1 FR 7614935 A FR7614935 A FR 7614935A FR 7614935 A FR7614935 A FR 7614935A FR 2351655 A1 FR2351655 A1 FR 2351655A1
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
Application number
FR7614935A
Other languages
French (fr)
Other versions
FR2351655B1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhone Poulenc Industries SA
Original Assignee
Rhone Poulenc Industries SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Rhone Poulenc Industries SA filed Critical Rhone Poulenc Industries SA
Priority to FR7614935A priority Critical patent/FR2351655A1/en
Priority to NLAANVRAGE7608444,A priority patent/NL169076C/en
Priority to OA55901A priority patent/OA05403A/en
Priority to GB32128/76A priority patent/GB1503091A/en
Priority to CS765082A priority patent/CS197276B2/en
Priority to CA258,441A priority patent/CA1073909A/en
Priority to IL50208A priority patent/IL50208A/en
Priority to DK353876AA priority patent/DK141069B/en
Priority to AU16615/76A priority patent/AU505316B2/en
Priority to IE1728/76A priority patent/IE44379B1/en
Priority to SE7608808A priority patent/SE422065B/en
Priority to MX762133U priority patent/MX3639E/en
Priority to AR264233A priority patent/AR211868A1/en
Priority to NO762729A priority patent/NO762729L/no
Priority to US05/711,963 priority patent/US4064247A/en
Priority to CH1004176A priority patent/CH612682A5/xx
Priority to JP51093548A priority patent/JPS5219699A/en
Priority to HU76RO00000892A priority patent/HU173003B/en
Priority to PT65442A priority patent/PT65442B/en
Priority to LU75540A priority patent/LU75540A1/xx
Priority to NZ181693A priority patent/NZ181693A/en
Priority to ES450530A priority patent/ES450530A1/en
Priority to FI762256A priority patent/FI60214C/en
Priority to PL1976191674A priority patent/PL108034B1/en
Priority to PL1976211043A priority patent/PL108413B1/en
Priority to AT586476A priority patent/AT350054B/en
Priority to DE2635516A priority patent/DE2635516C3/en
Priority to SU762386213A priority patent/SU629881A3/en
Priority to ES452987A priority patent/ES452987A1/en
Priority to AR267010A priority patent/AR211170A1/en
Priority to SU772504520A priority patent/SU635874A3/en
Priority to CS776704A priority patent/CS197277B2/en
Publication of FR2351655A1 publication Critical patent/FR2351655A1/en
Priority to AT397678A priority patent/AT352136B/en
Priority to AT397778A priority patent/AT351544B/en
Application granted granted Critical
Publication of FR2351655B1 publication Critical patent/FR2351655B1/fr
Granted legal-status Critical Current

Links

Classifications

    • 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.
FR7614935A 1975-08-06 1976-05-18 Pyridylimino or quinolylimino-tetrahydro-thiazolo-isoquinoline cpds. - are analgesics and antipyretics with some antiinflammatory activity Granted FR2351655A1 (en)

Priority Applications (34)

Application Number Priority Date Filing Date Title
FR7614935A FR2351655A1 (en) 1976-05-18 1976-05-18 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
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
CA258,441A CA1073909A (en) 1975-08-06 1976-08-04 Thiazolo (3,4-b)-isoquinoleine derivatives preparation and compositions thereof________________________________________________________________
HU76RO00000892A HU173003B (en) 1975-08-06 1976-08-05 Process for producing new thiasolo-bracket-3,4-b-bracket slosed-isoquinolines
IE1728/76A IE44379B1 (en) 1975-08-06 1976-08-05 Thiazolo (3,4-b)isoquinoline derivatives
SE7608808A SE422065B (en) 1975-08-06 1976-08-05 PROCEDURE FOR PREPARING NEW DERIVATIVES OF TIAZOLO- (3,4-B) -ISOKINOLINE
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
AR264233A AR211868A1 (en) 1975-08-06 1976-08-05 PROCEDURE TO OBTAIN NEW DERIVATIVES OF TETRAHYDRO-1,5,10A THIAZOL 3,4-B ISOQUINOLINE
NO762729A NO762729L (en) 1975-08-06 1976-08-05
US05/711,963 US4064247A (en) 1975-08-06 1976-08-05 Thiazolo[3,4-b]isoquinoline derivatives and pharmaceutical compositions containing them
CH1004176A CH612682A5 (en) 1975-08-06 1976-08-05
JP51093548A JPS5219699A (en) 1975-08-06 1976-08-05 Thiazolo *3*44b* isoquinoline derivative
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.
PT65442A PT65442B (en) 1975-08-06 1976-08-05 NOVEL THIAZOLO / 3,4-B / ISOQUINOLEINE DERIVATIVES FOR THEIR PREPARATION AND COMPOSITIONS CONTAINING THEM
LU75540A LU75540A1 (en) 1975-08-06 1976-08-05
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
ES450530A ES450530A1 (en) 1975-08-06 1976-08-06 Thiazolo{8 3,4-b{9 isoquinoline derivatives and pharmaceutical compositions containing them
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
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
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
DE2635516A DE2635516C3 (en) 1975-08-06 1976-08-06 New derivatives of thiazolo [3,4-b] isoquinoline, 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
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.
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
AT397678A AT352136B (en) 1976-05-18 1978-06-01 PROCESS FOR THE PREPARATION OF NEW 1,5,10,10A-TETRAHYDROTHIAZOLO- (3,4-B) -ISOCHINOLINE DERIVATIVES AND THEIR ACID ADDITIONAL 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
FR7614935A FR2351655A1 (en) 1976-05-18 1976-05-18 Pyridylimino or quinolylimino-tetrahydro-thiazolo-isoquinoline cpds. - are analgesics and antipyretics with some antiinflammatory activity

Publications (2)

Publication Number Publication Date
FR2351655A1 true FR2351655A1 (en) 1977-12-16
FR2351655B1 FR2351655B1 (en) 1978-10-20

Family

ID=9173277

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7614935A Granted FR2351655A1 (en) 1975-08-06 1976-05-18 Pyridylimino or quinolylimino-tetrahydro-thiazolo-isoquinoline cpds. - are analgesics and antipyretics with some antiinflammatory activity

Country Status (2)

Country Link
AT (1) AT352136B (en)
FR (1) FR2351655A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
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

Cited By (2)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
AT352136B (en) 1979-09-10
ATA397678A (en) 1979-02-15
FR2351655B1 (en) 1978-10-20

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