DE1445425C - - Google Patents
Info
- Publication number
- DE1445425C DE1445425C DE19631445425 DE1445425A DE1445425C DE 1445425 C DE1445425 C DE 1445425C DE 19631445425 DE19631445425 DE 19631445425 DE 1445425 A DE1445425 A DE 1445425A DE 1445425 C DE1445425 C DE 1445425C
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compound
- piperazine
- mol
- dimethylaminopropyl
- 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 claims description 41
- 150000004885 piperazines Chemical class 0.000 claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- -1 4-methoxyphenyl- Chemical group 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 11
- HXEWMTXDBOQQKO-UHFFFAOYSA-N 4,7-dichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC=C21 HXEWMTXDBOQQKO-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 230000004083 survival effect Effects 0.000 description 10
- 238000011081 inoculation Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- GJOHLWZHWQUKAU-UHFFFAOYSA-N 5-azaniumylpentan-2-yl-(6-methoxyquinolin-8-yl)azanium;dihydrogen phosphate Chemical compound OP(O)(O)=O.OP(O)(O)=O.N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 GJOHLWZHWQUKAU-UHFFFAOYSA-N 0.000 description 5
- 241000223109 Trypanosoma cruzi Species 0.000 description 5
- 229960005179 primaquine Drugs 0.000 description 5
- 125000005493 quinolyl group Chemical group 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000005528 methosulfate group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
- YJRGRZJKGMBHIB-UHFFFAOYSA-N n,n-dimethyl-3-piperazin-1-ylpropan-1-amine Chemical compound CN(C)CCCN1CCNCC1 YJRGRZJKGMBHIB-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- YCPXMJXDVLKMIU-SPIKMXEPSA-N (z)-but-2-enedioic acid;n-[4-[4-[3-(dimethylamino)propyl]piperazin-1-yl]phenyl]acetamide Chemical compound OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.C1CN(CCCN(C)C)CCN1C1=CC=C(NC(C)=O)C=C1 YCPXMJXDVLKMIU-SPIKMXEPSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 2
- MMXANKLJIHSIQH-UHFFFAOYSA-N 1-(4-methoxyphenyl)piperazine-1,4-diium;dichloride Chemical compound Cl.Cl.C1=CC(OC)=CC=C1N1CCNCC1 MMXANKLJIHSIQH-UHFFFAOYSA-N 0.000 description 1
- RVULOBVPCMOVMV-UHFFFAOYSA-N 2-phenyltriazole-4-carbonyl chloride Chemical compound N1=C(C(=O)Cl)C=NN1C1=CC=CC=C1 RVULOBVPCMOVMV-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 1
- KNDOFJFSHZCKGT-UHFFFAOYSA-N 4-chloroquinoline Chemical compound C1=CC=C2C(Cl)=CC=NC2=C1 KNDOFJFSHZCKGT-UHFFFAOYSA-N 0.000 description 1
- YVQVOQKFMFRVGR-VGOFMYFVSA-N 5-(morpholin-4-ylmethyl)-3-[(e)-(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OC(CN2CCOCC2)C1 YVQVOQKFMFRVGR-VGOFMYFVSA-N 0.000 description 1
- 206010001935 American trypanosomiasis Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZWCHCCNBXVUZHO-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.C(C=C/C(=O)O)(=O)O.C(C=C/C(=O)O)(=O)O.N1CCNCC1 Chemical compound C(C=C/C(=O)O)(=O)O.C(C=C/C(=O)O)(=O)O.C(C=C/C(=O)O)(=O)O.N1CCNCC1 ZWCHCCNBXVUZHO-UHFFFAOYSA-N 0.000 description 1
- 208000024699 Chagas disease Diseases 0.000 description 1
- RSOFRZVKSLAHAV-UHFFFAOYSA-N OP(O)(=O)OP(=O)(O)O.N1=CC=CC2=CC=CC=C12 Chemical compound OP(O)(=O)OP(=O)(O)O.N1=CC=CC2=CC=CC=C12 RSOFRZVKSLAHAV-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 241000223104 Trypanosoma Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical class NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- DRYNKPZTEPHVQP-UHFFFAOYSA-N n,n-dimethyl-3-[4-(4-nitrophenyl)piperazin-1-yl]propan-1-amine Chemical compound C1CN(CCCN(C)C)CCN1C1=CC=C([N+]([O-])=O)C=C1 DRYNKPZTEPHVQP-UHFFFAOYSA-N 0.000 description 1
- DPCSPGOPQYRPCP-UHFFFAOYSA-N n-[4-[4-[3-(dimethylamino)propyl]piperazin-1-yl]phenyl]acetamide Chemical compound C1CN(CCCN(C)C)CCN1C1=CC=C(NC(C)=O)C=C1 DPCSPGOPQYRPCP-UHFFFAOYSA-N 0.000 description 1
- BDXOFHUWOXMXTK-UHFFFAOYSA-N oxoplatinum hydrochloride Chemical compound [Pt]=O.Cl BDXOFHUWOXMXTK-UHFFFAOYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- VSUPQVVYJLCOGN-UHFFFAOYSA-N piperazine hydrate trihydrochloride Chemical compound O.Cl.Cl.Cl.N1CCNCC1 VSUPQVVYJLCOGN-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27053463A | 1963-04-04 | 1963-04-04 | |
| US27053763A | 1963-04-04 | 1963-04-04 | |
| US27053663A | 1963-04-04 | 1963-04-04 | |
| US27053663 | 1963-04-04 | ||
| US27053463 | 1963-04-04 | ||
| US27053763 | 1963-04-04 | ||
| DEA0043961 | 1963-09-02 | ||
| US37971464A | 1964-07-01 | 1964-07-01 | |
| US468143A US3331830A (en) | 1963-04-04 | 1965-06-29 | 1-substituted-4-substituted aminoalkylene piperazines |
| US468142A US3331843A (en) | 1963-04-04 | 1965-06-29 | 1-substituted-4-substituted aminoalkylene piperazines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1445425A1 DE1445425A1 (de) | 1968-10-31 |
| DE1445425C true DE1445425C (https=) | 1973-05-10 |
Family
ID=27559486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631445425 Granted DE1445425A1 (de) | 1963-04-04 | 1963-09-02 | Verfahren zur Herstellung von Piperazinderivaten |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US3331843A (https=) |
| BE (1) | BE637271A (https=) |
| BR (1) | BR6352303D0 (https=) |
| CH (1) | CH482691A (https=) |
| DE (1) | DE1445425A1 (https=) |
| FI (2) | FI41280C (https=) |
| FR (1) | FR3708M (https=) |
| GB (1) | GB1047935A (https=) |
| LU (1) | LU44424A1 (https=) |
| MC (1) | MC435A1 (https=) |
| NL (1) | NL297170A (https=) |
| NO (1) | NO117694B (https=) |
| SE (2) | SE320667B (https=) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1165283A (en) * | 1967-01-17 | 1969-09-24 | Science Union & Cie | New Purine Derivatives and processes for prepararing them |
| US3491098A (en) * | 1967-05-29 | 1970-01-20 | Sterling Drug Inc | 1-((imidazolyl)-lower-alkyl)-4-substituted-piperazines |
| GB1279843A (en) * | 1969-05-23 | 1972-06-28 | Science Union & Cie | Benzamidoethyl-piperazines and process for their preparation |
| US4081542A (en) * | 1975-04-21 | 1978-03-28 | Merck & Co., Inc. | Piperazinylpyrazines |
| CH653021A5 (fr) * | 1981-04-24 | 1985-12-13 | Delalande Sa | Derives piperidino, piperazino et homopiperazino, n-substitues par un groupe heterocyclique aromatique, leur procede de preparation et composition therapeutique les contenant. |
| US4457931A (en) * | 1982-09-27 | 1984-07-03 | Selvi & C. S.P.A. | Piperazine derivatives with anticholinergic and/or antihistaminic activity |
| NL8601494A (nl) * | 1985-06-22 | 1987-01-16 | Sandoz Ag | Thiazolen, hun bereiding en farmaceutische preparaten die ze bevatten. |
| US5057517A (en) * | 1987-07-20 | 1991-10-15 | Merck & Co., Inc. | Piperazinyl derivatives of purines and isosteres thereof as hypoglycemic agents |
| US4977156A (en) * | 1988-07-26 | 1990-12-11 | The Dow Chemical Company | Amino piperazine esters showing biocidal activity |
| US5032604A (en) * | 1989-12-08 | 1991-07-16 | Merck & Co., Inc. | Class III antiarrhythmic agents |
| JP3193560B2 (ja) * | 1993-04-16 | 2001-07-30 | 明治製菓株式会社 | 新規ベンゾオキサゾール誘導体 |
| EP1158983A4 (en) * | 1999-03-03 | 2003-05-21 | Merck & Co Inc | Prenyl protein transferase inhibitors |
| JP2002540072A (ja) * | 1999-03-03 | 2002-11-26 | メルク エンド カムパニー インコーポレーテッド | プレニル蛋白トランスフェラーゼの阻害剤 |
| AU5567000A (en) * | 1999-06-24 | 2001-01-09 | Toray Industries, Inc. | Alpha1b-adrenergic receptor antagonists |
| AU6936500A (en) * | 1999-08-24 | 2001-03-19 | Regents Of The University Of California, The | Non-quinoline inhibitors of malaria parasites |
| CA2475766C (en) * | 2002-03-13 | 2012-06-05 | Janssen Pharmaceutica N.V. | Piperazinyl-, piperidinyl- and morpholinyl-derivatives as novel inhibitors of histone deacetylase |
| MXPA04008797A (es) * | 2002-03-13 | 2004-11-26 | Janssen Pharmaceutica Nv | Inhibidores de histona desacetilasa. |
| HRP20040805A2 (en) | 2002-03-13 | 2005-04-30 | Janssen Pharmaceutica N.V. | Carbonylamino derivatives as novel inhibitors histone deacetylase |
| EA007099B1 (ru) | 2002-03-13 | 2006-06-30 | Янссен Фармацевтика Н. В. | Сульфонилпроизводные в качестве ингибиторов гистон-деацетилазы |
| KR101261305B1 (ko) | 2004-07-28 | 2013-05-08 | 얀센 파마슈티카 엔.브이. | 히스톤 디아세틸라제의 신규한 저해제로의 치환된 인돌릴알킬 아미노 유도체 |
| UY29177A1 (es) * | 2004-10-25 | 2006-05-31 | Astex Therapeutics Ltd | Derivados sustituidos de purina, purinona y deazapurina, composiciones que los contienen métodos para su preparación y sus usos |
| MY179032A (en) | 2004-10-25 | 2020-10-26 | Cancer Research Tech Ltd | Ortho-condensed pyridine and pyrimidine derivatives (e.g.purines) as protein kinase inhibitors |
| WO2006089076A2 (en) | 2005-02-18 | 2006-08-24 | Neurogen Corporation | Thiazole amides, imidazole amides and related analogues |
| ES2553178T3 (es) | 2005-05-18 | 2015-12-04 | Janssen Pharmaceutica N.V. | Derivados sustituidos de aminopropenil piperidina o morfolina como nuevos inhibidores de histona deacetilasa |
| EP1981875B1 (en) * | 2006-01-19 | 2014-04-16 | Janssen Pharmaceutica N.V. | Substituted indolyl-alkyl-amino-derivatives as inhibitors of histone deacetylase |
| WO2007082874A1 (en) * | 2006-01-19 | 2007-07-26 | Janssen Pharmaceutica N.V. | Pyridine and pyrimidine derivatives as inhibitors of histone deacetylase |
| WO2007082876A1 (en) * | 2006-01-19 | 2007-07-26 | Janssen Pharmaceutica N.V. | Pyridine and pyrimidine derivatives as inhibitors of histone deacetylase |
| CA2631876C (en) * | 2006-01-19 | 2014-05-27 | Janssen Pharmaceutica N.V. | Aminophenyl derivatives as inhibitors of histone deacetylase |
| DK3421471T3 (da) | 2006-04-25 | 2021-06-14 | Astex Therapeutics Ltd | Purin- og deazapurinderivater som farmaceutiske forbindelser |
| AU2008277796A1 (en) * | 2007-07-19 | 2009-01-22 | F. Hoffmann-La Roche Ag | Novel heterocyclyl compounds and their use as chemokine antagonists |
| DK2195293T3 (da) | 2007-08-22 | 2014-02-03 | Astrazeneca Ab | Cyclopropylamidderivater |
| PL2201012T3 (pl) | 2007-10-11 | 2014-11-28 | Astrazeneca Ab | Pochodne pirolo[2,3-d]pirymidyny jako inhibitory kinazy białkowej b |
| EP2212310A4 (en) * | 2007-10-15 | 2011-04-20 | Elder Pharmaceuticals Ltd | METHOD OF GENERATING BISCHINOLINE DERIVATIVES USING SOLELY N-MONOSUBSTITUTED PIPERAZINES FOR THE MOST IMPROVED METHOD |
| TW201039825A (en) * | 2009-02-20 | 2010-11-16 | Astrazeneca Ab | Cyclopropyl amide derivatives 983 |
| FR2945289A1 (fr) * | 2009-05-11 | 2010-11-12 | Sanofi Aventis | Derives de 2-cycloamino-5-(pyridin-4-yl)imidazo°2,1-b! °1,3,4!thiadiazole, leur preparation et leur application en therapeutique |
| WO2011095885A1 (en) * | 2010-02-08 | 2011-08-11 | Matrix Laboratories Ltd. | An improved process for the preparation of piperaquine |
| US20110201622A1 (en) * | 2010-02-18 | 2011-08-18 | Collins Craig D | Solid Forms Comprising A Cyclopropyl Amide Derivative |
| BR112012020629A2 (pt) | 2010-02-18 | 2018-06-19 | Astrazeneca Ab | forma cristalina, e, método para a terapia de um distúrbio |
| EA027506B1 (ru) | 2011-04-01 | 2017-08-31 | Астразенека Аб | Способ лечения рака молочной железы |
| US9206133B2 (en) * | 2011-06-06 | 2015-12-08 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Process for the synthesis of 7-chloro-4-(piperazin-1-yl)-quinoline |
| HRP20191982T4 (hr) | 2011-11-30 | 2023-01-06 | Astrazeneca Ab | Kombinacijsko liječenje raka |
| AU2013204533B2 (en) | 2012-04-17 | 2017-02-02 | Astrazeneca Ab | Crystalline forms |
| IL294124B2 (en) | 2015-12-10 | 2024-02-01 | Ptc Therapeutics Inc | Methods for treating huntington's disease |
| US11407753B2 (en) | 2017-06-05 | 2022-08-09 | Ptc Therapeutics, Inc. | Compounds for treating Huntington's disease |
| US11382918B2 (en) | 2017-06-28 | 2022-07-12 | Ptc Therapeutics, Inc. | Methods for treating Huntington's Disease |
| WO2019005993A1 (en) | 2017-06-28 | 2019-01-03 | Ptc Therapeutics, Inc. | METHODS OF TREATING HUNTINGTON'S DISEASE |
| MX2020009957A (es) | 2018-03-27 | 2021-01-15 | Ptc Therapeutics Inc | Compuestos para el tratamiento de enfermedad de hungtinton. |
| CN110606830B (zh) * | 2018-06-14 | 2022-03-18 | 珠海润都制药股份有限公司 | 一种哌嗪套用生产磷酸哌喹中间体喹啉哌嗪盐酸盐的方法 |
| PL3814357T3 (pl) | 2018-06-27 | 2024-09-16 | Ptc Therapeutics, Inc. | Związki heterocykliczne i heteroarylowe do leczenia choroby huntingtona |
| EP3814345B8 (en) | 2018-06-27 | 2024-10-30 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| EP3814360B8 (en) * | 2018-06-27 | 2024-11-06 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| WO2020231977A1 (en) | 2019-05-13 | 2020-11-19 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2513026A (en) * | 1950-06-27 | Process for preparing same | ||
| NL72956C (https=) * | 1947-11-12 | |||
| US2861072A (en) * | 1952-07-19 | 1958-11-18 | Abbott Lab | Preparation of piperazine derivatives |
| US2794804A (en) * | 1955-03-24 | 1957-06-04 | American Cyanamid Co | Substituted piperazines and method of preparing the same |
| US2949431A (en) * | 1957-07-17 | 1960-08-16 | Mobay Chemical Corp | Preparation of cellular polyurethanes using piperazine catalysts |
| US3098066A (en) * | 1960-03-04 | 1963-07-16 | Ciba Geigy Corp | Diaza-heterocyclic guanidine compounds |
| US3015657A (en) * | 1959-05-28 | 1962-01-02 | Charles F Geschickter | 1-carbalkoxy-4-(aminoalkanol) piperazines |
| US3030366A (en) * | 1961-01-25 | 1962-04-17 | Lakeside Lab Inc | Piperazinoalkyl glycolamides |
| FR1525M (fr) * | 1961-07-25 | 1962-11-16 | Ile De France | Médicaments antiémétiques nouveaux. |
| US3190883A (en) * | 1962-10-05 | 1965-06-22 | Geschickter Fund Med Res | Aminoalkanol derivatives of piperazines |
| US3184382A (en) * | 1963-08-12 | 1965-05-18 | Pure Oil Co | Method of producing tranquilization by hydroxy-loweralkyl-n-substituted carbamic acid esters |
-
0
- NL NL297170D patent/NL297170A/xx unknown
- BE BE637271D patent/BE637271A/xx unknown
-
1963
- 1963-08-06 GB GB30926/63A patent/GB1047935A/en not_active Expired
- 1963-08-28 BR BR152303/63A patent/BR6352303D0/pt unknown
- 1963-09-02 FI FI631675A patent/FI41280C/fi active
- 1963-09-02 SE SE9582/63A patent/SE320667B/xx unknown
- 1963-09-02 DE DE19631445425 patent/DE1445425A1/de active Granted
- 1963-09-02 NO NO149944A patent/NO117694B/no unknown
- 1963-09-10 MC MC453A patent/MC435A1/fr unknown
- 1963-09-11 LU LU44424D patent/LU44424A1/xx unknown
- 1963-09-16 FR FR947586A patent/FR3708M/fr not_active Expired
- 1963-09-16 CH CH1141863A patent/CH482691A/fr not_active IP Right Cessation
-
1965
- 1965-06-29 US US468142A patent/US3331843A/en not_active Expired - Lifetime
- 1965-06-29 US US468143A patent/US3331830A/en not_active Expired - Lifetime
-
1967
- 1967-05-26 SE SE7418/67A patent/SE346316B/xx unknown
-
1968
- 1968-04-04 FI FI680932A patent/FI42440C/fi active
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