GB1061247A - 1-aralkyl-4-(thiazolyl-2)-piperazines and preparation thereof - Google Patents
1-aralkyl-4-(thiazolyl-2)-piperazines and preparation thereofInfo
- Publication number
- GB1061247A GB1061247A GB3395/66A GB339566A GB1061247A GB 1061247 A GB1061247 A GB 1061247A GB 3395/66 A GB3395/66 A GB 3395/66A GB 339566 A GB339566 A GB 339566A GB 1061247 A GB1061247 A GB 1061247A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- piperazine
- reaction
- condensation
- 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
- 150000001875 compounds Chemical class 0.000 abstract 19
- 238000006243 chemical reaction Methods 0.000 abstract 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 8
- -1 methylene dioxy Chemical group 0.000 abstract 8
- 230000005494 condensation Effects 0.000 abstract 6
- 238000009833 condensation Methods 0.000 abstract 6
- 229910052801 chlorine Inorganic materials 0.000 abstract 5
- 239000000460 chlorine Substances 0.000 abstract 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 4
- 229910052794 bromium Inorganic materials 0.000 abstract 4
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 3
- 229910052740 iodine Inorganic materials 0.000 abstract 3
- 150000002825 nitriles Chemical class 0.000 abstract 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- TXFLGZOGNOOEFZ-UHFFFAOYSA-N bis(2-chloroethyl)amine Chemical compound ClCCNCCCl TXFLGZOGNOOEFZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 abstract 2
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 abstract 1
- UGTCVEYCIOVYME-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)propanoyl chloride Chemical compound ClC(=O)CCC1=CC=C2OCOC2=C1 UGTCVEYCIOVYME-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 108010010803 Gelatin Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 abstract 1
- 229920002472 Starch Polymers 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
- 239000002253 acid Substances 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000003974 aralkylamines Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 235000012000 cholesterol Nutrition 0.000 abstract 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 239000008273 gelatin Substances 0.000 abstract 1
- 229920000159 gelatin Polymers 0.000 abstract 1
- 235000019322 gelatine Nutrition 0.000 abstract 1
- 235000011852 gelatine desserts Nutrition 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- 239000008101 lactose Substances 0.000 abstract 1
- 235000019359 magnesium stearate Nutrition 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 235000019271 petrolatum Nutrition 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- IVXQBCUBSIPQGU-UHFFFAOYSA-N piperazine-1-carboxamide Chemical compound NC(=O)N1CCNCC1 IVXQBCUBSIPQGU-UHFFFAOYSA-N 0.000 abstract 1
- 150000004885 piperazines Chemical class 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 abstract 1
- 239000001294 propane Substances 0.000 abstract 1
- 238000006894 reductive elimination reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 235000012222 talc Nutrition 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 150000007979 thiazole derivatives Chemical class 0.000 abstract 1
- 150000003585 thioureas Chemical class 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract 1
- 239000008158 vegetable oil Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- D—TEXTILES; PAPER
- D05—SEWING; EMBROIDERING; TUFTING
- D05B—SEWING
- D05B7/00—Linking machines, e.g. for joining knitted fabrics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM0064244 | 1965-02-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1061247A true GB1061247A (en) | 1967-03-08 |
Family
ID=7311049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3395/66A Expired GB1061247A (en) | 1965-02-20 | 1966-01-25 | 1-aralkyl-4-(thiazolyl-2)-piperazines and preparation thereof |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3489757A (en:Method) |
| BE (1) | BE676686A (en:Method) |
| CH (2) | CH462176A (en:Method) |
| DE (1) | DE1595923A1 (en:Method) |
| ES (1) | ES323305A1 (en:Method) |
| FR (1) | FR5175M (en:Method) |
| GB (1) | GB1061247A (en:Method) |
| NL (1) | NL6601699A (en:Method) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5120736A (en) * | 1988-10-11 | 1992-06-09 | Institut De Recherches Chimiques Et Biologiques Appliquees | 4-methyl-5-(2-(4-phenylpiperazin-1-yl)ethyl)thiazole derivatives their method of preparation and the pharmaceutical compositions in which they are present |
| WO1994020494A1 (es) * | 1993-03-11 | 1994-09-15 | Vita-Invest, S.A. | Agente gastrocinetico, proceso para su preparacion y composiciones farmaceuticas que lo contengan |
| WO2017144637A1 (en) * | 2016-02-25 | 2017-08-31 | Asceneuron S. A. | Acid addition salts of piperazine derivatives |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH583232A5 (en:Method) * | 1973-02-02 | 1976-12-31 | Wander Ag Dr A | |
| US3907819A (en) * | 1973-05-14 | 1975-09-23 | Du Pont | Perhalogenated thiazoles |
| GB1560084A (en) * | 1976-12-31 | 1980-01-30 | Science Union & Cie | Disubstituted piperazines processes for their preparation and pharmaceutical mompositions containing them |
| OA06083A (fr) * | 1977-11-09 | 1981-06-30 | Science Union & Cie Ste Franca | Nouvelles pipérazines disubstituées, leurs procédés de préparation et les compositions pharmaceutiques les renfermant. |
| DE2961406D1 (en) * | 1978-04-13 | 1982-01-28 | Science Union & Cie | Monosubstituted piperazines, processes for their preparation and pharmaceutical compositions containing them |
| US4411900A (en) * | 1980-01-03 | 1983-10-25 | Fujisawa Pharmaceutical Co., Ltd. | Benzhydrylpiperozinyl thiazole derivatives and pharmaceutical composition comprising the same |
| US4647557A (en) * | 1982-12-28 | 1987-03-03 | Gerard Moinet | Novel heterocyclic derivatives bearing an amino radical, processes for their production and the pharmaceutical compositions containing them |
| HUT43600A (en) * | 1985-06-22 | 1987-11-30 | Sandoz Ag | Process for production of new thiazole derivatives and medical compound containing those |
| US4914112A (en) * | 1986-06-03 | 1990-04-03 | Sumitomo Pharmaceuticals Company, Limited | Aminoazole derivatives and their production and use |
| DE3812755A1 (de) * | 1988-04-16 | 1989-10-26 | Merck Patent Gmbh | Salicylsaeurederivate |
| TW200826936A (en) * | 2006-12-01 | 2008-07-01 | Merck Frosst Canada Ltd | Azacycloalkane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| SG11201701315VA (en) * | 2014-08-28 | 2017-03-30 | Asceneuron Sa | Glycosidase inhibitors |
| US11612599B2 (en) | 2016-02-25 | 2023-03-28 | Asceneuron Sa | Glycosidase inhibitors |
| EP3585783A2 (en) | 2016-02-25 | 2020-01-01 | Asceneuron SA | Sulfoximine glycosidase inhibitors |
| US11261183B2 (en) | 2016-02-25 | 2022-03-01 | Asceneuron Sa | Sulfoximine glycosidase inhibitors |
| CN108884078A (zh) | 2016-02-25 | 2018-11-23 | 阿森纽荣股份公司 | 糖苷酶抑制剂 |
| AU2017378186A1 (en) * | 2016-12-16 | 2019-06-13 | Janssen Pharmaceutica Nv | Monocyclic OGA inhibitor compounds |
| US11213525B2 (en) | 2017-08-24 | 2022-01-04 | Asceneuron Sa | Linear glycosidase inhibitors |
| WO2019037861A1 (en) | 2017-08-24 | 2019-02-28 | Asceneuron S.A. | ANNOTATED GLYCOSIDASE INHIBITORS |
| WO2020039028A1 (en) | 2018-08-22 | 2020-02-27 | Asceneuron S. A. | Tetrahydro-benzoazepine glycosidase inhibitors |
| MA53429A (fr) | 2018-08-22 | 2022-03-30 | Asceneuron Sa | Sels d'addition d'acide succinate et fumarate de dérivés de pipérazine utiles en tant qu'inhibiteurs de glycosidase |
| WO2020039029A1 (en) | 2018-08-22 | 2020-02-27 | Asceneuron S. A. | Spiro compounds as glycosidase inhibitors |
| US12016852B2 (en) | 2018-08-22 | 2024-06-25 | Asceneuron Sa | Pyrrolidine glycosidase inhibitors |
| US20220143042A1 (en) | 2019-02-22 | 2022-05-12 | Asceneuron Sa | Fused glycosidase inhibitors |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL72956C (en:Method) * | 1947-11-12 | |||
| DE1595920B2 (de) * | 1964-11-04 | 1978-08-10 | Merck Patent Gmbh, 6100 Darmstadt | 4-(co-Piperazinoalkyl)-pyrazole, ihre Salze und Verfahren zu ihrer Herstellung |
-
1965
- 1965-02-20 DE DE19651595923 patent/DE1595923A1/de active Pending
- 1965-12-30 CH CH233068A patent/CH462176A/de unknown
- 1965-12-30 CH CH1811465A patent/CH460787A/de unknown
-
1966
- 1966-01-25 GB GB3395/66A patent/GB1061247A/en not_active Expired
- 1966-02-10 NL NL6601699A patent/NL6601699A/xx unknown
- 1966-02-17 US US528058A patent/US3489757A/en not_active Expired - Lifetime
- 1966-02-18 FR FR49827A patent/FR5175M/fr not_active Expired
- 1966-02-18 BE BE676686D patent/BE676686A/xx unknown
- 1966-02-19 ES ES0323305A patent/ES323305A1/es not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5120736A (en) * | 1988-10-11 | 1992-06-09 | Institut De Recherches Chimiques Et Biologiques Appliquees | 4-methyl-5-(2-(4-phenylpiperazin-1-yl)ethyl)thiazole derivatives their method of preparation and the pharmaceutical compositions in which they are present |
| WO1994020494A1 (es) * | 1993-03-11 | 1994-09-15 | Vita-Invest, S.A. | Agente gastrocinetico, proceso para su preparacion y composiciones farmaceuticas que lo contengan |
| WO2017144637A1 (en) * | 2016-02-25 | 2017-08-31 | Asceneuron S. A. | Acid addition salts of piperazine derivatives |
| US10696668B2 (en) | 2016-02-25 | 2020-06-30 | Asceneuron Sa | Acid addition salts of piperazine derivatives |
| US11591327B2 (en) | 2016-02-25 | 2023-02-28 | Asceneuron Sa | Acid addition salts of piperazine derivatives |
| US12398130B2 (en) | 2016-02-25 | 2025-08-26 | Asceneuron Sa | Acid addition salts of piperazine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| US3489757A (en) | 1970-01-13 |
| BE676686A (en:Method) | 1966-08-18 |
| CH462176A (de) | 1968-09-15 |
| ES323305A1 (es) | 1967-03-16 |
| FR5175M (en:Method) | 1967-06-19 |
| NL6601699A (en:Method) | 1966-08-22 |
| CH460787A (de) | 1968-08-15 |
| DE1595923A1 (de) | 1969-11-27 |
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