GB1386038A - Thiazolopyrimidine derivatives and pharmaceutical compositions containing them - Google Patents
Thiazolopyrimidine derivatives and pharmaceutical compositions containing themInfo
- Publication number
- GB1386038A GB1386038A GB3767273A GB3767273A GB1386038A GB 1386038 A GB1386038 A GB 1386038A GB 3767273 A GB3767273 A GB 3767273A GB 3767273 A GB3767273 A GB 3767273A GB 1386038 A GB1386038 A GB 1386038A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- radical
- compounds
- defined above
- compound
- 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
Links
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 3
- 150000008634 thiazolopyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 4
- -1 aromatic radical Chemical class 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 239000002585 base Substances 0.000 abstract 2
- 150000003839 salts Chemical group 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 abstract 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- 101710178035 Chorismate synthase 2 Proteins 0.000 abstract 1
- 101710152694 Cysteine synthase 2 Proteins 0.000 abstract 1
- 101100533387 Homo sapiens SCGB1D1 gene Proteins 0.000 abstract 1
- 102100028659 Secretoglobin family 1D member 1 Human genes 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000002269 analeptic agent Substances 0.000 abstract 1
- 239000003146 anticoagulant agent Substances 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- C07D211/26—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 nitrogen 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
- C07D211/36—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 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 ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1386038 Thiazolepyrimidine derivatives and pharmaceutical compositions containing them LIPHA LYONNAISE INDUSTRIELLE PHARMACEUTIQUE 8 Aug 1973 [9 Aug 1972] 37672/73 Heading C2C The invention comprises heterocyclic compounds in salt form represented by formula and the corresponding bases thereof, wherein R is a C 4-8 alkyl group or a benzyl radical; R 1 is a hydroxy radical or a double bond in the 3,2- positions of the thiazolpyrimidine nucleus; R 2 is an aromatic radical selected from a phenyl radical optionally substituted by at least one halogen atom or alkoxy radical, a 2-naphthyl radical and a 5,6,7,8-tetrahydro-2-naphthyl radical; and X is a halogen atom or a pharmaceutically acceptable acid radical. The compounds of Formula I in which R 1 is a hydroxy radical may be prepared by treating an α- halogenated ketone of formula wherein Y is a halogen atom (e.g. Br), and R 2 is the same as defined above, with a compound of formula wherein R and Y have the same meanings as defined above, at a temperature of from ambient temperature to 50 C., in an inert solvent. When the reaction is carried out at 125 to 160 C, the compounds of Formula I, in which R 1 represents a double bond at 3,2-positions of the thiazolpyrimidine nucleus, are formed. The intermediate compounds of Formula II may be prepared by reacting a compound of formula wherein R has the same meaning as defined above, with CS 2 , and treating the product with a halo-acid to obtain a compound of Formula II. The compounds of Formula III may be obtained by the reduction of dinitriles of formula wherein R has the same meaning as defined above. The dinitriles of Formula IV may be prepared by the condensation of a chlorinated base of formula or an acid addition salt thereof, wherein R has the same meaning as given above, with a malonitrile in the presence of an acid acceptor, e.g. an alkali metal carbonate, and in an aprotic solvent. The invention also comprises a pharmaceutical composition, having utility as thymo-analeptic and platelet-anti-aggregant, containing as an active ingredient a compound according to the invention in association with a pharmaceutical carrier or excipient therefor.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7228747A FR2195426B1 (en) | 1972-08-09 | 1972-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1386038A true GB1386038A (en) | 1975-03-05 |
Family
ID=9103083
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3767273A Expired GB1386038A (en) | 1972-08-09 | 1973-08-08 | Thiazolopyrimidine derivatives and pharmaceutical compositions containing them |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3907800A (en) |
| JP (1) | JPS49132098A (en) |
| AT (1) | AT330173B (en) |
| AU (1) | AU5900173A (en) |
| BE (1) | BE803357A (en) |
| DD (1) | DD109875A5 (en) |
| DE (1) | DE2340122A1 (en) |
| ES (1) | ES417685A1 (en) |
| FR (1) | FR2195426B1 (en) |
| GB (1) | GB1386038A (en) |
| HU (1) | HU165953B (en) |
| IE (1) | IE37986B1 (en) |
| IL (1) | IL42913A0 (en) |
| NL (1) | NL7311048A (en) |
| SU (1) | SU506300A3 (en) |
| ZA (1) | ZA735351B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4489884A (en) * | 1980-10-10 | 1984-12-25 | Stedef S.A. | Railroad tie cover |
| US4880790A (en) * | 1986-01-31 | 1989-11-14 | American Cyanamid Company | (Gem-heterocyclodimethanamine-N,N')platinum complexes |
| US5057513A (en) * | 1989-05-25 | 1991-10-15 | Fujisawa Pharmaceutical Co., Ltd. | Spiro-thiazepine derivatives useful as paf antagonists |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH498139A (en) * | 1967-11-03 | 1970-10-31 | Sandoz Ag | Process for the preparation of new 3-phenyl-6,7-dihydro-5H-thiazolo (3,2-a) pyrimidines |
| US3560515A (en) * | 1968-08-05 | 1971-02-02 | Parke Davis & Co | New thiazolobenzodiazepine compounds and methods for their production |
| US3507868A (en) * | 1968-10-21 | 1970-04-21 | Sandoz Ag | Imidazo(2,1-b)thiazoles and thiazolo(3,2-a)pyrimidines |
| US3507869A (en) * | 1969-02-27 | 1970-04-21 | Sandoz Ag | Substituted thiazoles |
| GB1275804A (en) * | 1969-07-03 | 1972-05-24 | Seperic | Improvements in or relating to new sulphur containing derivatives of pyrimidine, their preparation and their applications |
| US3763142A (en) * | 1971-11-09 | 1973-10-02 | Sandoz Ag | Thiazolodiazepines |
-
1972
- 1972-08-09 FR FR7228747A patent/FR2195426B1/fr not_active Expired
-
1973
- 1973-08-06 US US385816A patent/US3907800A/en not_active Expired - Lifetime
- 1973-08-06 IL IL42913A patent/IL42913A0/en unknown
- 1973-08-06 ZA ZA735351A patent/ZA735351B/en unknown
- 1973-08-08 DD DD172768A patent/DD109875A5/xx unknown
- 1973-08-08 ES ES417685A patent/ES417685A1/en not_active Expired
- 1973-08-08 SU SU1954500A patent/SU506300A3/en active
- 1973-08-08 HU HULI247A patent/HU165953B/hu unknown
- 1973-08-08 BE BE134357A patent/BE803357A/en unknown
- 1973-08-08 DE DE19732340122 patent/DE2340122A1/en active Pending
- 1973-08-08 AU AU59001/73A patent/AU5900173A/en not_active Expired
- 1973-08-08 GB GB3767273A patent/GB1386038A/en not_active Expired
- 1973-08-09 NL NL7311048A patent/NL7311048A/xx unknown
- 1973-08-09 IE IE1366/73A patent/IE37986B1/en unknown
- 1973-08-09 AT AT699373A patent/AT330173B/en not_active IP Right Cessation
- 1973-08-09 JP JP48088925A patent/JPS49132098A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SU506300A3 (en) | 1976-03-05 |
| IE37986L (en) | 1974-02-09 |
| DE2340122A1 (en) | 1974-02-21 |
| JPS49132098A (en) | 1974-12-18 |
| AU5900173A (en) | 1975-02-13 |
| FR2195426B1 (en) | 1975-10-17 |
| IL42913A0 (en) | 1973-11-28 |
| IE37986B1 (en) | 1977-11-23 |
| NL7311048A (en) | 1974-02-12 |
| BE803357A (en) | 1973-12-03 |
| ATA699373A (en) | 1975-09-15 |
| AT330173B (en) | 1976-06-25 |
| ES417685A1 (en) | 1976-06-01 |
| DD109875A5 (en) | 1974-11-20 |
| ZA735351B (en) | 1974-07-31 |
| FR2195426A1 (en) | 1974-03-08 |
| US3907800A (en) | 1975-09-23 |
| HU165953B (en) | 1974-12-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES483767A1 (en) | Alpha-(N-arylsulfonyl-L-argininamides, processes for their preparation and pharmaceutical compositions containing these substances. | |
| GB1489394A (en) | Halogen-containing metal phthalocyanines and a process for their manufacture | |
| GB1325192A (en) | Phloroglucinol derivatives | |
| GB1411213A (en) | 1,3-dithiolo-4,5-6- quinoxalines process for their preparation and their use as insecticides acaricides and fungicides | |
| GB1441056A (en) | Phenyl-pyridazines their preparation and use as herbicides | |
| ES250753A1 (en) | Process for the preparation of o,o-dialkyl-dithiophosphoryl-fatty acid compounds and pesticidal compositions containing the same | |
| GB1386038A (en) | Thiazolopyrimidine derivatives and pharmaceutical compositions containing them | |
| GB1456627A (en) | Pyridobenzodiazepinones | |
| IE32223B1 (en) | Novel carboxylic acids,processes for their production and compositions containing the same | |
| GB1469060A (en) | Pyrimidinyl-thionophosphonic acid esters process for their preparation and their use as insecticides acaricides and nematocides | |
| US3692794A (en) | 1,2,4-thiadiazoles | |
| GB1128079A (en) | Process for the manufacture of new cyclohexane derivatives | |
| GB1502232A (en) | Substituted 2-phenylimino-1,3-dithiolanes process for their preparation and their use as ectoparasiticidal agents | |
| GB863550A (en) | 3-mercapto-phenthiazines | |
| ES371448A1 (en) | Derivatives of acetic acid | |
| GB1451690A (en) | O-aryl-thionoalkanephosphonic acid ester-imide derivatives a process for their preparation and their use as insecticides acaricides or nematocides | |
| GB1462098A (en) | Thiophosphonic acid ester derivatives having pesticidal properties | |
| US3679671A (en) | Oxidation of phenylacetonitrile derivatives employing a copper (ii)-amine catalyst system | |
| US3652566A (en) | 2-acylamino pyrimidin-4yl carbamates | |
| GB1528830A (en) | O-alkyl-o-phenylthionophosphonic acid esters containing a substituted formamidino group and their use as anthropodicides | |
| GB1313903A (en) | Phosphoric acid amide esters | |
| GB847550A (en) | Phosphonic acid esters | |
| GB1322860A (en) | Thiazolo-thiono-phosphoric phosphonic acid esters | |
| GB1412663A (en) | 2- 4-biphenylyl- tetrahydrofurans and pharmaceutical compositions containing them | |
| US3120555A (en) | Alkoxycarbonylalkyl halophenyl carbonates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |