RU98117621A - NEW DERIVATIVES OF PIPERASIN AND PIPERIDINE, METHOD FOR PRODUCING THEM, PHARMACEUTICAL COMPOSITION ON THEIR BASIS, METHOD OF TREATMENT, INTERMEDIATE PRODUCT - Google Patents
NEW DERIVATIVES OF PIPERASIN AND PIPERIDINE, METHOD FOR PRODUCING THEM, PHARMACEUTICAL COMPOSITION ON THEIR BASIS, METHOD OF TREATMENT, INTERMEDIATE PRODUCTInfo
- Publication number
- RU98117621A RU98117621A RU98117621/04A RU98117621A RU98117621A RU 98117621 A RU98117621 A RU 98117621A RU 98117621/04 A RU98117621/04 A RU 98117621/04A RU 98117621 A RU98117621 A RU 98117621A RU 98117621 A RU98117621 A RU 98117621A
- Authority
- RU
- Russia
- Prior art keywords
- group
- formula
- compound
- salts
- alkyl
- Prior art date
Links
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000011780 sodium chloride Substances 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- -1 cyano, aminocarbonyl Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000004885 piperazines Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004429 atoms Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005842 heteroatoms Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Claims (6)
А представляет гетероциклическую группу с 5 - 7 атомами в кольце, где присутствуют 1 - 3 гетероатома, из группы O, N и S,
R1 представляет водород или фтор,
R2 представляет С1-4-алкил, С1-4-алкокси или оксо - группу и р равно 0, 1 или 2,
Z представляет углерод или азот и пунктирная линия представляет одинарную связь, когда Z представляет азот, и одинарную или двойную связь, когда Z представляет углерод,
R3 и R4 независимо, представляют водород или С1-4-алкил,
n равно 1 или 2,
R5 представляет 2-пиридил, 3-пиридил или 4-пиридил, замещенный в мета-положении относительно метиленового мостика группой Y и необязательно замещенный заместителем (R6)q,
Y представляет фенил, фуранил или тиенил, причем эти группы могут быть замещены 1 - 3 заместителями из группы, включающей гидрокси, галоген, CF3, C1-4-алкокси, С1-4-алкил, циано, аминокарбонил, моно- или ди-С1-4-алкиламинокарбонил,
R6 представляет галоген, гидрокси, С1-4-алкокси или С1-4 алкил, и q равно 0, 1, 2 или 3, и их соли.1. Derivatives of piperazine and piperidine of the General formula
A represents a heterocyclic group with 5 to 7 atoms in the ring, where 1 to 3 heteroatoms are present, from the group O, N and S,
R 1 represents hydrogen or fluorine,
R 2 represents a C 1-4 alkyl, a C 1-4 alkoxy or oxo group and p is 0, 1 or 2,
Z represents carbon or nitrogen and the dotted line represents a single bond when Z represents nitrogen, and a single or double bond when Z represents carbon,
R 3 and R 4 independently represent hydrogen or C 1-4 alkyl,
n is 1 or 2,
R 5 represents 2-pyridyl, 3-pyridyl or 4-pyridyl substituted in the meta position relative to the methylene bridge with group Y and optionally substituted with the substituent (R 6 ) q ,
Y represents phenyl, furanyl or thienyl, these groups being optionally substituted with 1 to 3 substituents from the group consisting of hydroxy, halogen, CF 3 , C 1-4 alkoxy, C 1-4 alkyl, cyano, aminocarbonyl, mono- or di-C 1-4 -alkylaminocarbonyl,
R 6 represents halogen, hydroxy, C 1-4 alkoxy or C 1-4 alkyl, and q is 0, 1, 2 or 3, and their salts.
и n равно 1, и R1 и (R2)p, R3, R4, R5, (R6)q, Y и Z имеют значения, данные в п.1, и его соли.2. The compound according to claim 1, in which a together with a phenyl group represents a group of the formula b, c, d, e, f or g:
and n is 1, and R 1 and (R 2 ) p , R 3 , R 4 , R 5 , (R 6 ) q , Y and Z have the meanings given in claim 1, and its salts.
с соединением формулы R5 - CH2 - X, где Х представляет отщепляемую группу, где значения R1, R2, R3, R4, A, Z, p и n указаны в п.1, или в) реакцию соединения формулы:
где R'5 имеет такие же значения, как R5, подразумевая, что атом брома находится в мета-положении относительно метиленового мостика, с соединением формулы В(ОН)2-Y, где R1, R2, R3, R4, A, Z, p и n имеют значения, данные в п.1.5. A method of obtaining derivatives of piperazine and piperidine of the formula 1, as defined in claim 1, characterized in that they carry out: a) a reaction of a compound of the formula:
with a compound of the formula R 5 - CH 2 - X, where X is a leaving group, wherein the values of R 1 , R 2 , R 3 , R 4 , A, Z, p and n are indicated in claim 1, or c) a reaction of a compound of the formula :
where R ' 5 has the same meanings as R 5 , meaning that the bromine atom is in the meta position relative to the methylene bridge, with a compound of formula B (OH) 2 -Y, where R 1 , R 2 , R 3 , R 4 , A, Z, p and n have the meanings given in claim 1.
где R1, (R2)p, Z, n, R3 и R4 имеют значение, данное в п.1, и R'5 имеет значение, указанное в п.5.6. The compound of the formula
where R 1 , (R 2 ) p , Z, n, R 3 and R 4 have the meaning given in claim 1, and R ' 5 has the meaning indicated in claim 5.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97202950.8 | 1997-09-24 | ||
| EP97202950 | 1997-09-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98117621A true RU98117621A (en) | 2000-06-20 |
| RU2197488C2 RU2197488C2 (en) | 2003-01-27 |
Family
ID=8228755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98117621/04A RU2197488C2 (en) | 1997-09-24 | 1998-09-21 | Derivatives of piperazine |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US6090812A (en) |
| EP (1) | EP0908458B1 (en) |
| JP (1) | JP4191826B2 (en) |
| KR (1) | KR100632188B1 (en) |
| CN (1) | CN1093857C (en) |
| AR (1) | AR017127A1 (en) |
| AT (1) | ATE316529T1 (en) |
| AU (1) | AU733526B2 (en) |
| BR (1) | BR9803497A (en) |
| CA (1) | CA2247734C (en) |
| CY (1) | CY1107494T1 (en) |
| CZ (1) | CZ296741B6 (en) |
| DE (1) | DE69833297T2 (en) |
| DK (1) | DK0908458T3 (en) |
| DZ (1) | DZ2613A1 (en) |
| ES (1) | ES2255127T3 (en) |
| HK (1) | HK1018272A1 (en) |
| HU (1) | HU227422B1 (en) |
| ID (1) | ID20895A (en) |
| IL (1) | IL126295A (en) |
| NO (1) | NO312835B1 (en) |
| NZ (1) | NZ331984A (en) |
| PL (1) | PL190622B1 (en) |
| PT (1) | PT908458E (en) |
| RU (1) | RU2197488C2 (en) |
| SI (1) | SI0908458T1 (en) |
| SK (1) | SK285205B6 (en) |
| TR (1) | TR199801866A1 (en) |
| TW (1) | TW530054B (en) |
| UA (1) | UA66756C2 (en) |
| ZA (1) | ZA988749B (en) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6200994B1 (en) | 1999-01-07 | 2001-03-13 | American Home Products Corp | 1,4-Disubstituted cyclohexane derivatives for the treatment of depression |
| WO2000040579A1 (en) * | 1999-01-07 | 2000-07-13 | American Home Products Corporation | New 1,4-disubstituted cyclohexane derivatives for the treatment of depression |
| DE10005150A1 (en) * | 2000-02-07 | 2001-08-09 | Merck Patent Gmbh | Process for the preparation of 5-arylnicotinaldehydes |
| DE10115922A1 (en) * | 2001-03-30 | 2002-10-10 | Bayer Ag | Cyclically substituted 2-thio-3,5-dicyano-4-aryl-6-aminopyridines and their use |
| EP1408976B3 (en) | 2001-07-20 | 2010-08-25 | Psychogenics Inc. | Treatment for attention-deficit hyperactivity disorder |
| US7435738B2 (en) | 2003-08-18 | 2008-10-14 | Solvay Pharmaceuticals, Inc. | Stable crystalline form of bifeprunox mesylate (7-[4-([1,1′-biphenyl]-3-ylmethyl)-1-piperazinyl]-2(3H)-benzoxazolone monomethanesulfonate) |
| US7405216B2 (en) | 2004-08-18 | 2008-07-29 | Solvay Pharmaceuticals, B.V. | Stable crystalline form of bifeprunox mesylate (7-[4-([1,1′-biphenyl]-3-ylmethyl)-1-piperazinyl]-2(3H)-benzoxazolone monomethanesulfonate) |
| US7423040B2 (en) | 2005-02-18 | 2008-09-09 | Irene Eijgendaal | Stable crystalline form of bifeprunox mesylate, dosage forms thereof and methods for using same |
| US7964604B2 (en) | 2005-02-18 | 2011-06-21 | Solvay Pharmaceuticals B.V. | Bifeprunox mesylate maintenance dose compositions and methods for using the same |
| US20070275977A1 (en) * | 2006-05-02 | 2007-11-29 | Van Aar Marcel P | N-oxides of pyridylmethyl -piperazine and -piperidine derivatives |
| AU2007247251B2 (en) | 2006-05-02 | 2011-11-03 | Solvay Pharmaceuticals B.V. | N-oxides of pyridylmethylpiperazine and -piperidine derivatives |
| US8106056B2 (en) | 2006-06-16 | 2012-01-31 | Solvay Pharmaceuticals B.V. | Combination preparations comprising bifeprunox and a dopamine agonist |
| US7786126B2 (en) | 2006-06-16 | 2010-08-31 | Solvay Pharmaceuticals B.V. | Combination preparations comprising SLV308 and a dopamine agonist |
| WO2011088838A1 (en) | 2010-01-25 | 2011-07-28 | H. Lundbeck A/S | Novel 6,6a,7,8,9,10-hexahydro-4h-4,8,10a-triaza-acephenanthrylene derivatives as dopamine d2 ligands |
| US8877778B2 (en) | 2010-12-15 | 2014-11-04 | Hoffmann-La Roche Inc. | Benzofurane compounds |
| US8921397B2 (en) | 2011-05-04 | 2014-12-30 | Hoffmann-La Roche Inc. | Benzofurane-piperidine compounds |
| TWI806385B (en) | 2016-07-20 | 2023-06-21 | 瑞士商諾華公司 | Aminopyridine derivatives and their use as selective alk-2 inhibitors |
| KR101665971B1 (en) | 2016-08-10 | 2016-10-13 | (주)글로벌 로보틱스 | Automotive foam pad attachment |
| CN115038443A (en) | 2019-11-22 | 2022-09-09 | 因西特公司 | Combination therapy comprising an ALK2 inhibitor and a JAK2 inhibitor |
| IL298767A (en) | 2020-06-16 | 2023-02-01 | Incyte Corp | Alk2 inhibitors for the treatment of anemia |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0190472B1 (en) * | 1984-12-21 | 1989-07-12 | Duphar International Research B.V | New pharmaceutical compositions having anti-psychotic properties |
| DE3586794T2 (en) | 1984-12-21 | 1993-05-27 | Duphar Int Res | MEDICINAL PRODUCTS WITH PSYCHOTROPER EFFECT. |
| PH22783A (en) * | 1986-02-27 | 1988-12-12 | Duphar Int Res | New aryl-substituted (n-piperidinyl)methyl-and (n-piperazinyl)methylazoles and pharmaceutical compositions containing the same |
| EP0508347A1 (en) | 1991-04-10 | 1992-10-14 | Hoechst Aktiengesellschaft | 5,7-Dihydroxy-2-methyl-8-[4-(3-hydroxy-1-(1-propyl)) piperidinyl]-4H-1-benzopyran-4-one, its preparation and its use |
| IE914218A1 (en) * | 1991-09-11 | 1993-03-24 | Mcneilab Inc | Novel 4-arylpiperazines and 4-arylpiperidines |
| JPH05262765A (en) | 1992-03-18 | 1993-10-12 | Sumitomo Chem Co Ltd | Benzofuran derivative and herbicide containing the same as active ingredient |
| FR2692264B1 (en) | 1992-06-12 | 1994-08-05 | Adir | NOVEL 1,4-DISUBSTITUTED PIPERAZINES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
| US5332732A (en) * | 1992-09-11 | 1994-07-26 | Mcneilab, Inc. | Thiophene and pyridine antipsychotic agents |
| US5436246A (en) * | 1992-09-17 | 1995-07-25 | Merrell Dow Pharmaceuticals Inc. | Serotonin receptor agents |
| RU2118322C1 (en) * | 1993-07-05 | 1998-08-27 | Дюфар Интернэшнл Рисерч Б.В. | 2,3-dihydro-1,4-benzodioxine-5-yl-pyrerazine derivatives and salts thereof |
| GB9314758D0 (en) * | 1993-07-16 | 1993-08-25 | Wyeth John & Brother Ltd | Heterocyclic derivatives |
| EP0650964A1 (en) | 1993-11-02 | 1995-05-03 | Duphar International Research B.V | 1 2H-1-benzopyran-2-one-8-yl -piperazine derivatives |
| DE4425146A1 (en) * | 1994-07-15 | 1996-01-18 | Basf Ag | Use of heterocyclic compounds |
| US5607936A (en) * | 1994-09-30 | 1997-03-04 | Merck & Co., Inc. | Substituted aryl piperazines as neurokinin antagonists |
| US6114334A (en) * | 1995-07-13 | 2000-09-05 | Knoll Aktiengesellschaft | Piperazine derivatives as therapeutic agents |
| PL189256B1 (en) * | 1996-03-29 | 2005-07-29 | Duphar Int Res | Chemical compounds of piperazine and piperidine |
| DE19637237A1 (en) | 1996-09-13 | 1998-03-19 | Merck Patent Gmbh | Piperazine derivatives |
-
1998
- 1998-09-11 TW TW087115179A patent/TW530054B/en not_active IP Right Cessation
- 1998-09-18 IL IL12629598A patent/IL126295A/en not_active IP Right Cessation
- 1998-09-21 RU RU98117621/04A patent/RU2197488C2/en not_active IP Right Cessation
- 1998-09-21 EP EP98203154A patent/EP0908458B1/en not_active Expired - Lifetime
- 1998-09-21 CN CN98119652A patent/CN1093857C/en not_active Expired - Fee Related
- 1998-09-21 ID IDP981269A patent/ID20895A/en unknown
- 1998-09-21 TR TR1998/01866A patent/TR199801866A1/en unknown
- 1998-09-21 BR BR9803497-9A patent/BR9803497A/en not_active IP Right Cessation
- 1998-09-21 AU AU86079/98A patent/AU733526B2/en not_active Ceased
- 1998-09-21 HU HU9802129A patent/HU227422B1/en not_active IP Right Cessation
- 1998-09-21 PT PT98203154T patent/PT908458E/en unknown
- 1998-09-21 CZ CZ0303098A patent/CZ296741B6/en not_active IP Right Cessation
- 1998-09-21 NZ NZ331984A patent/NZ331984A/en not_active IP Right Cessation
- 1998-09-21 NO NO19984380A patent/NO312835B1/en not_active IP Right Cessation
- 1998-09-21 CA CA002247734A patent/CA2247734C/en not_active Expired - Fee Related
- 1998-09-21 JP JP28357898A patent/JP4191826B2/en not_active Expired - Lifetime
- 1998-09-21 PL PL98328754A patent/PL190622B1/en not_active IP Right Cessation
- 1998-09-21 AT AT98203154T patent/ATE316529T1/en active
- 1998-09-21 ES ES98203154T patent/ES2255127T3/en not_active Expired - Lifetime
- 1998-09-21 KR KR1019980038929A patent/KR100632188B1/en not_active IP Right Cessation
- 1998-09-21 SK SK1294-98A patent/SK285205B6/en not_active IP Right Cessation
- 1998-09-21 DE DE69833297T patent/DE69833297T2/en not_active Expired - Lifetime
- 1998-09-21 AR ARP980104704A patent/AR017127A1/en active IP Right Grant
- 1998-09-21 SI SI9830822T patent/SI0908458T1/en unknown
- 1998-09-21 DK DK98203154T patent/DK0908458T3/en active
- 1998-09-22 DZ DZ980223A patent/DZ2613A1/en active
- 1998-09-22 US US09/158,520 patent/US6090812A/en not_active Ceased
- 1998-09-22 UA UA98094970A patent/UA66756C2/en unknown
- 1998-09-23 ZA ZA988749A patent/ZA988749B/en unknown
-
1999
- 1999-08-03 HK HK99103334A patent/HK1018272A1/en not_active IP Right Cessation
-
2006
- 2006-04-07 CY CY20061100484T patent/CY1107494T1/en unknown
-
2008
- 2008-04-18 US US12/081,710 patent/USRE41425E1/en not_active Expired - Lifetime
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