GB1215132A - Physiologically active amine derivatives of thiophthalane - Google Patents

Physiologically active amine derivatives of thiophthalane

Info

Publication number
GB1215132A
GB1215132A GB44560/67A GB4456067A GB1215132A GB 1215132 A GB1215132 A GB 1215132A GB 44560/67 A GB44560/67 A GB 44560/67A GB 4456067 A GB4456067 A GB 4456067A GB 1215132 A GB1215132 A GB 1215132A
Authority
GB
United Kingdom
Prior art keywords
alkyl
reacting
acid
alkylene
thiophthalane
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
Application number
GB44560/67A
Inventor
Povl Viggo Petersen
Niels Lassen
Thorkil Ammitzboll
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.)
Kefalas AS
Original Assignee
Kefalas AS
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 Kefalas AS filed Critical Kefalas AS
Priority to GB44560/67A priority Critical patent/GB1215132A/en
Priority to AT1184968A priority patent/AT276374B/en
Priority to AT19068A priority patent/AT276373B/en
Priority to AT1185068A priority patent/AT276375B/en
Priority to BE709229D priority patent/BE709229A/xx
Priority to ES349217A priority patent/ES349217A1/en
Priority to DE19681668925 priority patent/DE1668925B1/en
Priority to CH1085470A priority patent/CH516577A/en
Priority to CH1085370A priority patent/CH522667A/en
Priority to CH45968A priority patent/CH510041A/en
Priority to DK11868A priority patent/DK128813B/en
Priority to NO16068A priority patent/NO121670B/no
Priority to NL6800637A priority patent/NL6800637A/xx
Priority to SE55968A priority patent/SE351652B/xx
Priority to FR1583194D priority patent/FR1583194A/fr
Priority to FR136254A priority patent/FR8378M/fr
Priority to FI11568A priority patent/FI49978C/en
Publication of GB1215132A publication Critical patent/GB1215132A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,215,132. Amine derivatives of thiophthalone- KEFALAS A.S. 15 Jan., 1968 [16 Jan., 1967; 29 Sept., 1967], Nos. 2327/67 and 44560/67. Heading C2C. [Also in Division A5] The invention comprises compounds of formula wherein R<SP>1</SP> and R<SP>2</SP> are H or C 1-8 alkyl, R<SP>3</SP> and R<SP>4</SP> are H, C 1-8 alkyl or benzyl, or NR<SP>3</SP>R<SP>4</SP> is a 5- or 6- membered saturated heterocyclic ring, "alkylene" is C 2-6 alkylene having at least 2 C atoms in the direct chain between the ring C and N atoms, R<SP>5</SP> is CONHR<SP>6</SP>, CO 2 R<SP>7</SP>, COR<SP>8</SP>, CHOHR<SP>8</SP> or Ph (optionally substituted with Y (halogen), C 1-8 alkyl, C 1-8 alkoxy or CY 3 ), R<SP>6</SP> is H, C 1-8 alkyl or Ph (optionally substituted with C 1-8 alkyl or C 1-8 alkoxy), R<SP>7</SP> is H or C 1-8 alkyl, R<SP>8</SP> is C 1-8 alkyl, Ph or Ph-C 1-8 -alkyl, and X is H, Y, C 1-8 alkyl, C 1-8 alkoxy or CY 3 ; and acid addition salts thereof with pharmaceutically acceptable acids. These compounds may be prepared by (a) condensing the corresponding thiophthalane having H instead of 'alkylene NR<SP>3</SP>R<SP>4</SP>', with Y-alkylene-NR<SP>3</SP>R<SP>4</SP>, (b) reacting the corresponding thiophthalane having Y instead of 'NR<SP>3</SP>R<SP>4</SP>', with HNR<SP>3</SP>R<SP>4</SP>, (c) reacting with H 2 S the corresponding #-(o-alkenylphenyl)- alk-#-enylamine, (d) monodealkylating the above compound (R<SP>3</SP>=C 1-8 alkyl, R<SP>4</SP>=C 1-8 alkyl or benzyl) by reaction with a C 1-8 alkyl or benzyl chloroformate followed by hydrolysis; (e) (for R<SP>5</SP>=CONHR<SP>6</SP>), reacting the above compound (R<SP>5</SP>=CO 2 R<SP>7</SP>) with R<SP>6</SP>NHMgY, (f) (for R<SP>5</SP>=COR<SP>8</SP> or CHOHR<SP>8</SP>) reacting the above compound (R<SP>5</SP> = CONH 2 ) with R<SP>8</SP>MgY, hydrolysing the mixture with dilute acid and optionally reducing the COR<SP>8</SP> group to CHOHR<SP>8</SP>. Starting materials and intermediates.- α-Phenylphthalyl dibromide (reacting o-benzoylbenzoic acid with LiAlH 4 and the product with PBr 3 ) reacts with Na 2 S to give 1-phenylthiophthalane; the 3-methyl homologue is made analogously. 2 - Benzylthio - 2 - (o - chlorophenyl)- propane (from benzylthiol and 2-(o-chlorophenyl)propan-2-ol (I)) reacts with NaH to give 1,1 - dimethyl - 3 - phenylthiophthalane (II). II is also made by (a) reducing its 3-hydroxy derivative (from o-isopropenylbenzophenone (III) and H 2 S) with formic acid, or (b) reacting III directly with H 2 S. o-Acetylbenzhydrol (from 3-phenylphthalide and MeMgI) is reduced with LiAlH 4 to α-methyl-α<SP>1</SP> -phenylphthalyl alcohol. 1 - (o - isopropenylphenyl) - 1 - phenyl - 4 - dimethylaminobut-1-ene is made by dehydrating the corresponding benzhydrol with SOCl 2 / pyridine. 1,1 - Dimethyl - 3 - N - ethoxycarbonyl- N - methylaminopropyl - 3 - phenylthiophthalane is made from the dimethylamino analogue with ClCO 2 Et. 2 - (Carboxymethylthio)- 2 - (o-chlorophenyl) propane (from thioglycollic acid and I) is ring-closed with NaH/Me 2 SO to 1,1-dimethylthiophthalane - 3 - carboxylic acid; the latter is converted conventionally to its acid chloride, amide, and methyl and ethyl esters.
GB44560/67A 1967-01-13 1967-09-29 Physiologically active amine derivatives of thiophthalane Expired GB1215132A (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
GB44560/67A GB1215132A (en) 1967-01-16 1967-09-29 Physiologically active amine derivatives of thiophthalane
AT1184968A AT276374B (en) 1967-01-16 1968-01-09 Process for the preparation of new 1-aminoalkyl-thiophthalanes and their acid addition salts
AT19068A AT276373B (en) 1967-01-16 1968-01-09 Process for the preparation of new 1-aminoalkyl-thiophthalanes and their acid addition salts
AT1185068A AT276375B (en) 1967-01-16 1968-01-09 Process for the preparation of new 1-aminoalkyl-thiophthalanes and their acid addition salts
BE709229D BE709229A (en) 1967-01-16 1968-01-11
ES349217A ES349217A1 (en) 1967-01-13 1968-01-12 Electrooptic spectrometer for the obtaining of the rapid lift and with high resolution of the spectral profile of a luminous source. (Machine-translation by Google Translate, not legally binding)
DE19681668925 DE1668925B1 (en) 1967-01-16 1968-01-12 Benzo [c] thiacyclopentenes and psychotherapeutic agents containing them
CH1085470A CH516577A (en) 1967-01-16 1968-01-12 1-Amino alkyl substd. thiophthalanes
CH1085370A CH522667A (en) 1967-01-16 1968-01-12 Process for the preparation of new 1-aminoalkyl-thiophthalanes and their acid addition salts
CH45968A CH510041A (en) 1967-01-16 1968-01-12 Process for the preparation of new 1-aminoalkyl-thiophthalanes or their acid addition salts and their use
DK11868A DK128813B (en) 1967-01-16 1968-01-15 Analogous process for the preparation of basic substituted thiophthalanes or acid addition salts thereof.
NO16068A NO121670B (en) 1967-01-16 1968-01-15
NL6800637A NL6800637A (en) 1967-01-16 1968-01-16
SE55968A SE351652B (en) 1967-01-16 1968-01-16
FR1583194D FR1583194A (en) 1967-01-16 1968-01-16
FR136254A FR8378M (en) 1967-01-16 1968-01-16
FI11568A FI49978C (en) 1967-01-16 1968-01-16 Process for the preparation of therapeutically active, basic substituted thiophthalanes or their acid addition salts.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB232767 1967-01-16
GB44560/67A GB1215132A (en) 1967-01-16 1967-09-29 Physiologically active amine derivatives of thiophthalane

Publications (1)

Publication Number Publication Date
GB1215132A true GB1215132A (en) 1970-12-09

Family

ID=26237442

Family Applications (1)

Application Number Title Priority Date Filing Date
GB44560/67A Expired GB1215132A (en) 1967-01-13 1967-09-29 Physiologically active amine derivatives of thiophthalane

Country Status (11)

Country Link
AT (3) AT276373B (en)
BE (1) BE709229A (en)
CH (2) CH510041A (en)
DE (1) DE1668925B1 (en)
DK (1) DK128813B (en)
FI (1) FI49978C (en)
FR (2) FR1583194A (en)
GB (1) GB1215132A (en)
NL (1) NL6800637A (en)
NO (1) NO121670B (en)
SE (1) SE351652B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2548186A1 (en) * 1983-07-01 1985-01-04 Delalande Sa New 3-amino thiophthalide and isobenzofuranthione derivatives, process for their preparation and their application in therapeutics
AT387183B (en) * 1983-10-05 1988-12-12 Distropat Ag METHOD FOR FOAMING A PART FROM POLYURETHANE FOAM ON AT LEAST ONE PART FROM WOOD OR WOOD-LIKE MATERIALS

Also Published As

Publication number Publication date
AT276373B (en) 1969-11-25
FR1583194A (en) 1969-10-24
NL6800637A (en) 1968-07-17
FI49978B (en) 1975-07-31
SE351652B (en) 1972-12-04
BE709229A (en) 1968-07-11
CH510041A (en) 1971-07-15
DK128813B (en) 1974-07-08
DE1668925B1 (en) 1972-06-08
FI49978C (en) 1975-11-10
AT276375B (en) 1969-11-25
FR8378M (en) 1971-03-01
NO121670B (en) 1971-03-29
AT276374B (en) 1969-11-25
CH522667A (en) 1972-05-15

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