RU99106804A - DERIVATIVES OF PIPERAZINE WITH ELECTORAL ACTION IN RELATION TO D4 RECEPTOR - Google Patents
DERIVATIVES OF PIPERAZINE WITH ELECTORAL ACTION IN RELATION TO D4 RECEPTORInfo
- Publication number
- RU99106804A RU99106804A RU99106804/04A RU99106804A RU99106804A RU 99106804 A RU99106804 A RU 99106804A RU 99106804/04 A RU99106804/04 A RU 99106804/04A RU 99106804 A RU99106804 A RU 99106804A RU 99106804 A RU99106804 A RU 99106804A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compound
- piperazine
- group
- physiologically acceptable
- Prior art date
Links
- 150000004885 piperazines Chemical class 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 8
- 239000011780 sodium chloride Substances 0.000 claims 8
- 230000003993 interaction Effects 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- -1 3-thienyl pyridyl Chemical group 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 230000000875 corresponding Effects 0.000 claims 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229940066771 systemic antihistamines Piperazine derivatives Drugs 0.000 claims 2
- NPQVEJQJZDMKCV-UHFFFAOYSA-N 2-[4-[(5-thiophen-3-ylpyridin-3-yl)methyl]piperazin-1-yl]pyrimidine Chemical compound C=1N=CC(C2=CSC=C2)=CC=1CN(CC1)CCN1C1=NC=CC=N1 NPQVEJQJZDMKCV-UHFFFAOYSA-N 0.000 claims 1
- HSIMYBORWJJPOY-UHFFFAOYSA-N 2-[4-[[3-(3-fluorophenyl)phenyl]methyl]piperazin-1-yl]pyrimidine Chemical compound FC1=CC=CC(C=2C=C(CN3CCN(CC3)C=3N=CC=CN=3)C=CC=2)=C1 HSIMYBORWJJPOY-UHFFFAOYSA-N 0.000 claims 1
- CQTUBBGJACSDPZ-UHFFFAOYSA-N 2-[4-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]piperazin-1-yl]pyrimidine Chemical compound C1=CC(F)=CC=C1C1=CN=CC(CN2CCN(CC2)C=2N=CC=CN=2)=C1 CQTUBBGJACSDPZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- RSMZVBCDMGDTMY-UHFFFAOYSA-N 4-[4-[(3-phenylphenyl)methyl]piperazin-1-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1N1CCN(CC=2C=C(C=CC=2)C=2C=CC=CC=2)CC1 RSMZVBCDMGDTMY-UHFFFAOYSA-N 0.000 claims 1
- 101700036312 CONA Proteins 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 239000003638 reducing agent Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
Claims (7)
в которой R1 обозначает незамещенный либо однократно замещенный Ph или 2- либо 3- тиенилом пиридил или фенил;
R2 обозначает Ph' или Het;
Ph и Ph' обозначают соответственно независимо друг от друга фенил, причем оба остатка соответственно могут быть незамещены либо одно-, дву- или трехкратно замещены F, Сl, Вr, I, ОН, ОА, A, CF3, NO2, CN, COA, CONH2, CONHA, CONA2 или 2- либо 3-тиенилом;
Het представляет собой насыщенный, частично либо полностью ненасыщенный моно- или бициклический гетероциклический остаток с 5-10 членами цикла, где могут быть представлены 1 либо 2 N-атома и/или 1 либо 2 O-атома, а гетероциклический остаток может быть одно- или двукратно замещен F, Сl, Вr, I, ОА, CF3, А или NO2, и
А обозначает алкил с 1-6 С-атомами,
а также их физиологически приемлемые соли.1. Piperazine derivatives of the formula I
in which R 1 denotes unsubstituted or singly substituted with Ph or 2- or 3-thienyl pyridyl or phenyl;
R 2 is Ph 'or Het;
Ph and Ph 'are, respectively, independently of each other phenyl, and both residues, respectively, can be unsubstituted or substituted once, twice or three times by F, Cl, Br, I, OH, OA, A, CF 3 , NO 2 , CN, COA, CONH 2 , CONHA, CONA 2 or 2-or 3-thienyl;
Het is a saturated, partially or fully unsaturated mono- or bicyclic heterocyclic residue with 5-10 cycle members, where 1 or 2 N-atoms and / or 1 or 2 O-atoms can be represented, and the heterocyclic residue can be single or F is substituted by F, Cl, Br, I, OA, CF 3 , A or NO 2 , and
And denotes alkyl with 1-6 C-atoms,
and their physiologically acceptable salts.
а также их соли.2. The compound according to claim 1, selected from the group including (a) 1- (2-pyrimidinyl) -4- (3- (3-thienylbenzyl) piperazine, (b) 1- [5- (4-fluorophenyl) pyrid -3-ylmethyl] -4- (2-pyrimidyl) piperazine, (c) 4- [4- (3-biphenylylmethyl) -1-piperazinyl] benzonitrile, (g) 1- (4-chlorophenyl) -4- [5 - (4-fluorophenyl) -3-pyridylmethyl) piperazine, (e) 1- (3'-fluoro-3-biphenylylmethyl) -4- (2-pyrimidinyl) piperazine, (e) 2- [4- (5- ( 3-thienyl) -3-pyridylmethyl) -1-piperazinyl] pyrimidine,
and their salts.
в которой R2 имеет указанное значение,
подвергают взаимодействию с соединением формулы III
в которой L представляет собой Cl, Br, I, OH, O-CO-A, O-CO-Ph, O-SO2-Ar, где Ar обозначает фенил или толил, а А обозначает алкил, или другую реакционноспособно этерифицированную ОН-группу либо легко нуклеофильно замещаемую уходящую группу, и в которой R1 имеет указанное значение,
или что соединение формулы IV
в которой R2 имеет указанное значение,
подвергают взаимодействию с соединением формулы V
в которой Х1 и Х2 могут иметь идентичное или разное значение либо обозначать Cl, Br, I, ОН или реакционноспособную функционально модифицированную ОН-группу, а R1 имеет указанное значение,
или что соединение формулы VI
в которой R2, X1 и X2 имеют указанные значения,
подвергают взаимодействию с соединением формулы VII
в которой R1 имеет указанное значение,
или что какое-либо соединение, соответствующее формуле I, но содержащее вместо одного или нескольких атомов водорода одну или несколько восстанавливаемых групп и/или одну или несколько дополнительных С-С-связей и/или С-N-связей, обрабатывают восстановителем, или что какое-либо соединение, соответствующее формуле I, но содержащее вместо одного или нескольких атомов водорода одну или несколько сольволизуемых групп, обрабатывают сольволизатором, и/или что при необходимости остаток R1 и/или R2 превращают в другой остаток R1 и/или R2 за счет того, что, например, ОА-группу расщепляют с образованием ОН-группы и/или дериватизируют CN-, СООН-, СООА-группу и/или что, например, алкилируют первичный либо вторичный N-атом и/или что полученное основание либо кислоту формулы I путем обработки кислотой либо основанием превращают в одну из их солей.3. The method of obtaining piperazine derivatives of formula 1 according to claim 1 and their salts, characterized in that the compound of formula II
in which R 2 has the indicated value,
subjected to interaction with the compound of the formula III
in which L represents Cl, Br, I, OH, O-CO-A, O-CO-Ph, O-SO 2 -Ar, where Ar denotes phenyl or tolyl, and A denotes alkyl, or another reactive esterified with OH- a group or an easily nucleophilically substitutable leaving group, and in which R 1 has the indicated value,
or that compound of formula IV
in which R 2 has the indicated value,
subjected to interaction with the compound of the formula V
in which X 1 and X 2 can have the same or different meaning or denote by Cl, Br, I, OH or a reactive functionally modified OH group, and R 1 has the indicated value,
or that compound of formula VI
in which R 2 , X 1 and X 2 have the indicated meanings,
subjected to interaction with the compound of the formula VII
in which R 1 has the indicated value,
or that any compound corresponding to formula I, but containing instead of one or more hydrogen atoms one or more reducible groups and / or one or more additional C-C-bonds and / or C-N-bonds, is treated with a reducing agent, or that any compound corresponding to formula I, but containing instead of one or several hydrogen atoms one or more solvilizable groups is treated with a solvolizer, and / or, if necessary, the residue R 1 and / or R 2 is converted into another residue R 1 and / or R 2 due to the fact that, for example, the OA group is cleaved to form the OH group and / or CN-, COOH-, COOA-group is derived and / or that, for example, primary or secondary N-atom is alkylated and / or that the resulting base or acid is of formula I by treatment with acid or base is converted into one of their salts.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19637237A DE19637237A1 (en) | 1996-09-13 | 1996-09-13 | Piperazine derivatives |
DE19637237.2 | 1996-09-13 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU99106804A true RU99106804A (en) | 2001-02-20 |
RU2180660C2 RU2180660C2 (en) | 2002-03-20 |
Family
ID=7805470
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU99106804/04A RU2180660C2 (en) | 1996-09-13 | 1997-09-03 | Piperazine derivatives, method of preparation thereof, and pharmaceutical composition |
Country Status (23)
Country | Link |
---|---|
US (1) | US6258813B1 (en) |
EP (1) | EP0931067B1 (en) |
JP (1) | JP2001500142A (en) |
KR (1) | KR20000036085A (en) |
CN (1) | CN1114594C (en) |
AR (1) | AR009770A1 (en) |
AT (1) | ATE219768T1 (en) |
AU (1) | AU724374B2 (en) |
BR (1) | BR9712037A (en) |
CA (1) | CA2266050C (en) |
CZ (1) | CZ292210B6 (en) |
DE (2) | DE19637237A1 (en) |
DK (1) | DK0931067T3 (en) |
ES (1) | ES2178011T3 (en) |
HU (1) | HUP9904521A3 (en) |
NO (1) | NO312589B1 (en) |
PL (1) | PL332081A1 (en) |
PT (1) | PT931067E (en) |
RU (1) | RU2180660C2 (en) |
SK (1) | SK282708B6 (en) |
UA (1) | UA57749C2 (en) |
WO (1) | WO1998011068A1 (en) |
ZA (1) | ZA978194B (en) |
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-
1996
- 1996-09-13 DE DE19637237A patent/DE19637237A1/en not_active Withdrawn
-
1997
- 1997-03-09 UA UA99041976A patent/UA57749C2/en unknown
- 1997-09-03 US US09/254,489 patent/US6258813B1/en not_active Expired - Fee Related
- 1997-09-03 PL PL97332081A patent/PL332081A1/en unknown
- 1997-09-03 RU RU99106804/04A patent/RU2180660C2/en not_active IP Right Cessation
- 1997-09-03 DK DK97944823T patent/DK0931067T3/en active
- 1997-09-03 AT AT97944823T patent/ATE219768T1/en not_active IP Right Cessation
- 1997-09-03 DE DE59707613T patent/DE59707613D1/en not_active Expired - Fee Related
- 1997-09-03 KR KR1019997002097A patent/KR20000036085A/en not_active Application Discontinuation
- 1997-09-03 CN CN97197883A patent/CN1114594C/en not_active Expired - Fee Related
- 1997-09-03 EP EP97944823A patent/EP0931067B1/en not_active Expired - Lifetime
- 1997-09-03 CZ CZ1999824A patent/CZ292210B6/en not_active IP Right Cessation
- 1997-09-03 CA CA002266050A patent/CA2266050C/en not_active Expired - Fee Related
- 1997-09-03 ES ES97944823T patent/ES2178011T3/en not_active Expired - Lifetime
- 1997-09-03 HU HU9904521A patent/HUP9904521A3/en unknown
- 1997-09-03 BR BR9712037A patent/BR9712037A/en not_active IP Right Cessation
- 1997-09-03 PT PT97944823T patent/PT931067E/en unknown
- 1997-09-03 SK SK303-99A patent/SK282708B6/en unknown
- 1997-09-03 JP JP10513215A patent/JP2001500142A/en not_active Ceased
- 1997-09-03 AU AU46203/97A patent/AU724374B2/en not_active Ceased
- 1997-09-03 WO PCT/EP1997/004789 patent/WO1998011068A1/en not_active Application Discontinuation
- 1997-09-11 ZA ZA978194A patent/ZA978194B/en unknown
- 1997-09-12 AR ARP970104189A patent/AR009770A1/en not_active Application Discontinuation
-
1999
- 1999-03-12 NO NO19991236A patent/NO312589B1/en not_active IP Right Cessation
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