RU99115750A - NEW CONNECTIONS WITH AN ANALYZING EFFECT - Google Patents
NEW CONNECTIONS WITH AN ANALYZING EFFECTInfo
- Publication number
- RU99115750A RU99115750A RU99115750/04A RU99115750A RU99115750A RU 99115750 A RU99115750 A RU 99115750A RU 99115750/04 A RU99115750/04 A RU 99115750/04A RU 99115750 A RU99115750 A RU 99115750A RU 99115750 A RU99115750 A RU 99115750A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compound
- independently
- hydrogen
- defined above
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 150000002431 hydrogen Chemical class 0.000 claims 13
- 125000001424 substituent group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000004429 atoms Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 238000002560 therapeutic procedure Methods 0.000 claims 5
- 208000008665 Gastrointestinal Disease Diseases 0.000 claims 4
- 208000001016 Spinal Injury Diseases 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
- 125000005418 aryl aryl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
- 239000000032 diagnostic agent Substances 0.000 claims 2
- 238000003379 elimination reaction Methods 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 229940113083 morpholine Drugs 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- -1 2 -cyclopropyl Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims 1
- 102000001708 Protein Isoforms Human genes 0.000 claims 1
- 108010029485 Protein Isoforms Proteins 0.000 claims 1
- 210000002820 Sympathetic Nervous System Anatomy 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 150000001860 citric acid derivatives Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000002146 gastrointestinal system disease Diseases 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrugs Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 0 C*C(CC1)CCC1C1(c2c1ccc(C(N)=O)c2)c1c(C)cccc1C Chemical compound C*C(CC1)CCC1C1(c2c1ccc(C(N)=O)c2)c1c(C)cccc1C 0.000 description 2
- JYJOZMOJSILMFX-UHFFFAOYSA-N CC(c1cc(C(C(CC2)CCC2=N)c(cc2)ccc2C(N)=O)ccc1)=O Chemical compound CC(c1cc(C(C(CC2)CCC2=N)c(cc2)ccc2C(N)=O)ccc1)=O JYJOZMOJSILMFX-UHFFFAOYSA-N 0.000 description 1
- HRSKGVZEADEQQC-CPRJBALCSA-N CCC(CC)C(c(cc1)ccc1C(c1ccccc1)=C(CC1)CCC1C([C@H](CCCCN)N)=O)=O Chemical compound CCC(CC)C(c(cc1)ccc1C(c1ccccc1)=C(CC1)CCC1C([C@H](CCCCN)N)=O)=O HRSKGVZEADEQQC-CPRJBALCSA-N 0.000 description 1
- QXTNVAYWQBEAHM-UHFFFAOYSA-N CCc1cc(C(C2CCCCC2)c(cc2)ccc2C(N)=O)cc(CC)c1 Chemical compound CCc1cc(C(C2CCCCC2)c(cc2)ccc2C(N)=O)cc(CC)c1 QXTNVAYWQBEAHM-UHFFFAOYSA-N 0.000 description 1
- YOKBEXLHNNVASQ-UHFFFAOYSA-N Cc1cc(C(C(CC2)CCC2=N)c(cc2)ccc2C(N)=O)ccc1 Chemical compound Cc1cc(C(C(CC2)CCC2=N)c(cc2)ccc2C(N)=O)ccc1 YOKBEXLHNNVASQ-UHFFFAOYSA-N 0.000 description 1
- QFIQTUZHXAVZKJ-UHFFFAOYSA-N NC(c1ccc(C(C(CC2)CCC2=N)c2ccccc2C=O)cc1)=O Chemical compound NC(c1ccc(C(C(CC2)CCC2=N)c2ccccc2C=O)cc1)=O QFIQTUZHXAVZKJ-UHFFFAOYSA-N 0.000 description 1
Claims (1)
где R1 выбирают из водорода, разветвленного или неразветвленного C1-C6-алкила, C1-C6-алкенила, C3-C8-циклоалкила, C4-C8-(алкилциклоалкила), где алкил представляет C1-C2-алкил, и циклоалкил представляет C3-C6-циклоалкил;
C6-C10-арила или гетероарила, имеющего от 5 до 10 атомов, выбранных из С, S, N и О; где арил или гетероарил может быть необязательно и независимо замещен 1 или 2 заместителями, независимо выбранными из водорода, CH3, -(CH2)pCF3, галогена, -CONR5R4, -COOR5, -COR5, -(CH2)pNR5R4, -(СН2)pСН3(СН2)pSОR5R4, -(CH2)pSO2R5 и -(CH2)pSO2NR5, где R4 и R5, каждый независимо такие, как определено выше для R1, и р равно 0, 1 или 2;
(C1-C2-алкил)-(C6-C10-арила) или (C1-C2-алкил)гетероарила, причем гетероарильные части имеют от 5 до 10 атомов, выбранных из С, S, N и О, и где арил или гетероарил может быть необязательно и независимо замещен 1 или 2 заместителями, независимо выбранными из водорода, CH3, -(CH2)qCF3, галогена, -CONR5R4, -COOR5, -COR5, -(CH2)qNR5R4, -(CH2)qCH3(CH2)qSOR5R4,
-(CH2)qSO2R5, -(CH2)qSO2NR5 и -(CH2)pOR5, где R4 и R5, каждый независимо, такой, как определено выше для R1, и q равно 0, 1 или 2; и
где R18, R19, R20, R21, R22, R23, R24 и R25, каждый независимо, представляют водород, C1-C6-алкил или C1-C6-алкенил;
R2 и R3, каждый независимо, представляют водород или C1-C6-алкил;
А выбирают из
где R8, R9, R10, R11, R12, R13, R14, R15, R16 и R17, каждый независимо, такие как определено выше для R1, и где фенильное кольцо каждого заместителя А может быть необязательно и независимо замещено по любому положению фенильного кольца 1 или 2 заместителями Z1 и Z2, которые, каждый независимо, выбирают из водорода, CH3, -(CH2)qCF3, галогена, -CONR6R7, -COOR6, -COR6, -(CH2)rNR6R7, -(СН2)rСН3(СН2)rSОR6, -(CH2)rSO2R6 и -(CH2)rSO2NR6R7, где R6 и R7, каждый независимо, такие, как определено выше для R1, и r равно 0, 1 или 2;
Q представляет C5-C6-гидроарильный или гетерогидроароматический радикал, имеющий 5 или 6 атомов, выбранных из С, S, N и O; C5-C6-циклоалкил или гетероциклоалкил, имеющий 5 или 6 атомов, выбранных из С, S, N и O; и где каждый Q необязательно может быть замещен заместителем Z1 и Z2, как определено выше;
В представляет замещенную или незамещенную ароматическую, гетероароматическую, гидроароматическую или гетерогидроароматическую часть, имеющую от 5 до 10 атомов, выбранных из С, S, N и О, и необязательно и независимо замещенную 1 или 2 заместителями, независимо выбранными из водорода, CH3, -(CH2)tCF3, галогена, -(CH2)tCONR5R4, -(CH2)tNR5R4, -(CH2)tCOR5,
-(CH2)tCOOR5, -OR5, -(СН2)tSОR5, -(CH2)tSO2R5 и -(CH2)tSO2NR5R4, где R4 и R5, каждый независимо, такие, как определено выше для R1, и t равно 0, 1, 2 или 3; и
R4 и R5, каждый независимо, такие, как определено выше для R1,
а также фармацевтически приемлемые соли соединений формулы (I) и их изомеры, гидраты, изоформы и пролекарства.1. The compound of General formula (I)
where R 1 is selected from hydrogen, branched or unbranched C 1 -C 6 -alkyl, C 1 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 4 -C 8 - (alkylcycloalkyl), where alkyl represents C 1 - C 2 -alkyl, and cycloalkyl is C 3 -C 6 -cycloalkyl;
C 6 -C 10 -aryl or heteroaryl having from 5 to 10 atoms selected from C, S, N and O; wherein aryl or heteroaryl may be optionally and independently substituted with 1 or 2 substituents independently selected from hydrogen, CH 3 , - (CH 2 ) p CF 3 , halogen, -CONR 5 R 4 , -COOR 5 , -COR 5 , - ( CH 2 ) p NR 5 R 4 , - (CH 2 ) p CH 3 (CH 2 ) p SOR 5 R 4 , - (CH 2 ) p SO 2 R 5 and - (CH 2 ) p SO 2 NR 5 , where R 4 and R 5 are each independently as defined above for R 1 , and p is 0, 1 or 2;
(C 1 -C 2 -alkyl) - (C 6 -C 10 -aryl) or (C 1 -C 2 -alkyl) heteroaryl, the heteroaryl moieties having from 5 to 10 atoms selected from C, S, N and O , and where aryl or heteroaryl may be optionally and independently substituted with 1 or 2 substituents independently selected from hydrogen, CH 3 , - (CH 2 ) q CF 3 , halogen, -CONR 5 R 4 , -COOR 5 , -COR 5 , - (CH 2 ) q NR 5 R 4 , - (CH 2 ) q CH 3 (CH 2 ) q SOR 5 R 4 ,
- (CH 2 ) q SO 2 R 5 , - (CH 2 ) q SO 2 NR 5 and - (CH 2 ) p OR 5 , where R 4 and R 5 , each independently, is as defined above for R 1 , and q is 0, 1, or 2; and
where R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 and R 25 each independently represent hydrogen, C 1 -C 6 alkyl or C 1 -C 6 alkenyl;
R 2 and R 3 each independently represent hydrogen or C 1 -C 6 alkyl;
And choose from
where R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 , each independently, such as defined above for R 1 , and where the phenyl ring of each substituent A can be optionally and independently substituted at any position of the phenyl ring 1 or 2 by the substituents Z 1 and Z 2 , which are each independently selected from hydrogen, CH 3 , - (CH 2 ) q CF 3 , halogen, —CONR 6 R 7 , - COOR 6 , -COR 6 , - (CH 2 ) r NR 6 R 7 , - (CH 2 ) r CH 3 (CH 2 ) r SOR 6 , - (CH 2 ) r SO 2 R 6 and - (CH 2 ) r SO 2 NR 6 R 7 where R 6 and R 7 are each independently such as defined above for R 1 and r is 0, 1 or 2;
Q represents a C 5 -C 6 -hydroaryl or heterohydroaromatic radical having 5 or 6 atoms selected from C, S, N and O; C 5 -C 6 -cycloalkyl or heterocycloalkyl having 5 or 6 atoms selected from C, S, N and O; and wherein each Q may optionally be substituted with a substituent Z 1 and Z 2 as defined above;
B represents a substituted or unsubstituted aromatic, heteroaromatic, hydroaromatic or heterohydroaromatic part having from 5 to 10 atoms selected from C, S, N and O and optionally and independently substituted with 1 or 2 substituents independently selected from hydrogen, CH 3 , - (CH 2 ) t CF 3 , halogen, - (CH 2 ) t CONR 5 R 4 , - (CH 2 ) t NR 5 R 4 , - (CH 2 ) t COR 5 ,
- (CH 2 ) t COOR 5 , -OR 5 , - (CH 2 ) t SOR 5 , - (CH 2 ) t SO 2 R 5 and - (CH 2 ) t SO 2 NR 5 R 4 , where R 4 and R 5 is each independently as defined above for R 1 , and t is 0, 1, 2 or 3; and
R 4 and R 5 each independently are as defined above for R 1 ,
as well as pharmaceutically acceptable salts of the compounds of formula (I) and their isomers, hydrates, isoforms, and prodrugs.
А выбирают из
где R8, R9, R10, R11, R12, R13, R14, R15, R16 и R17, каждый независимо, такие как определено выше для R1, и где фенильное кольцо каждого заместителя А может быть необязательно и независимо замещено по любому положению фенильного кольца 1 или 2 заместителями Z1 и Z2, которые, каждый независимо, выбирают из водорода, CH3, -(CH2)qCF3, галогена, -CONR6R7, -COOR6, -COR6, -(СН2)rNR6R7, -(CH2)rCH3(CH2)rSOR6, -(CH2)rSO2R6 и -(CH2)rSO2NR6R7, где R6 и R7, каждый независимо, такие, как определено выше для R1, и r равно 0, 1 или 2;
Q выбирают из морфолина, пиперидина и пирролидина; R1, R4 и R5, каждый независимо, выбирают из водорода, разветвленного или неразветвленного С1-С4-алкила, С3-С5-циклоалкила, С4-С8-(алкилциклоалкила), где алкил представляет С1-С2-алкил, и циклоалкил представляет С3-С6-циклоалкил; С6-С10-арила и гетероарила, имеющего от 5 до 6 атомов, выбранных из С, S, N и О; и где арил или гетероарил может быть необязательно и независимо замещен 1 или 2 заместителями, независимо выбранными из водорода, CH3, -(CH2)pCF3, галогена, -CONR5R4, -COOR5, -COR5, -(CH2)pNR5R4, -(CH2)pCH3(CH2)pSOR5R4,
-(CH2)pSO2R5 и -(CH2)pSO2NR5, где R4 и R5, каждый независимо, такие, как определено выше для R1, и р равно 0, 1 или 2;
В выбирают из фенила, нафтила, индолила, бензофуранила, дигидробензофуранила, бензотиофенила, пиррила, фуранила, хинолинила, изохинолинила, циклогексила, циклогексенила, циклопентила, циклопентенила, инданила, инденила, тетрагидронафтила, тетрагидрохинила, тетрагидроизохинолинила, тетрагидрофуранила, пирролидинила и индазолинила, каждый из которых необязательно и независимо замещен 1 или 2 заместителями, независимо выбранными из водорода, CH3, CF3, галогена, -(CH2)qCONR5R4, -(CH2)qNR5R4, -(CH2)qCOR5,
-C(CH2)qCO2R5 и -OR5, где q равно 0 или 1, и где R4 и R5 такие, как определено выше;
R2 и R3, каждый независимо, представляют водород или метил.2. The compound of formula (I) according to claim 1, where
And choose from
where R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 , each independently, such as defined above for R 1 , and where the phenyl ring of each substituent A can be optionally and independently substituted at any position of the phenyl ring 1 or 2 by the substituents Z 1 and Z 2 , which are each independently selected from hydrogen, CH 3 , - (CH 2 ) q CF 3 , halogen, —CONR 6 R 7 , - COOR 6 , -COR 6 , - (CH 2 ) r NR 6 R 7 , - (CH 2 ) r CH 3 (CH 2 ) r SOR 6 , - (CH 2 ) r SO 2 R 6 and - (CH 2 ) r SO 2 NR 6 R 7 where R 6 and R 7 are each independently such as defined above for R 1 and r is 0, 1 or 2;
Q is selected from morpholine, piperidine and pyrrolidine; R 1 , R 4 and R 5 are each independently selected from hydrogen, branched or unbranched C 1 -C 4 alkyl, C 3 -C 5 cycloalkyl, C 4 -C 8 - (alkylcycloalkyl), where alkyl is C 1 -C 2 -alkyl, and cycloalkyl is C 3 -C 6 -cycloalkyl; C 6 -C 10 -aryl and heteroaryl having from 5 to 6 atoms selected from C, S, N and O; and where aryl or heteroaryl may be optionally and independently substituted with 1 or 2 substituents independently selected from hydrogen, CH 3 , - (CH 2 ) p CF 3 , halogen, -CONR 5 R 4 , -COOR 5 , -COR 5 , - (CH 2 ) p NR 5 R 4 , - (CH 2 ) p CH 3 (CH 2 ) p SOR 5 R 4 ,
- (CH 2 ) p SO 2 R 5 and - (CH 2 ) p SO 2 NR 5 , where R 4 and R 5 , each independently, are as defined above for R 1 , and p is 0, 1 or 2;
In the past, in the world optionally and independently substituted with 1 or 2 substituents independently selected from hydrogen, CH 3 , CF 3 , halogen, - (CH 2 ) q CONR 5 R 4 , - (CH 2 ) q NR 5 R 4 , - (CH 2 ) q COR 5 ,
—C (CH 2 ) q CO 2 R 5 and —OR 5 , where q is 0 or 1, and where R 4 and R 5 are as defined above;
R 2 and R 3 each independently represent hydrogen or methyl.
где R8 и R9, оба представляют этил, и где фенильное кольцо необязательно и независимо, может быть замещено по любому положению фенильного кольца двумя заместителями Z1 и Z2, которые, каждый независимо, выбирают из водорода, CH3, -(CH2)qCF3, галогена, -CONR6R7, -COOR6, -COR6, -(CH2)rNR6R7,
-(СН2)rСН3(СН2)rSОR6, -(CH2)rSO2R6 и -(CH2)rSO2NR6R7, где R6 и R7, каждый независимо, такие, как определено выше для R1, и r равно 0, 1 или 2;
R1 выбирают из водорода, метила, этила, -CH2CH=CH2, -CH2-циклопропила, -CH2-арила или CH2-гетероарила, причем гетероарильные части имеют от 5 до 6 атомов, выбранных из С, S, N и О;
В выбирают из фенила, нафтила, индолила, бензофуранила, дигидробензофуранила, бензотиофенила, фуранила, хинолинила, изохинолинила, циклогексила, циклогексенила, циклопентила, циклопентенила, инданила, инденила, тетрагидронафтила, тетрагидрохинила, тетрагидроизохинолинила, тетрагидрофуранила и индазолинила, каждый из которых необязательно и независимо замещен 1 или 2 заместителями, независимо выбранными из водорода, СН3, СF3, галогена, -(CH2)qCONR5R4, -(CH2)qNR5R4, -(CH2)qCOR5, -(CH2)qCO2R5 и -OR5, где q равно 0 или 1, и где R4 и R5 такие, как определено выше;
R2 и R3, каждый независимо, представляет водород или метил.3. The compound of formula (I) according to claim 2, wherein A is
where R 8 and R 9 both represent ethyl, and where the phenyl ring may optionally and independently be substituted at any position of the phenyl ring by two substituents Z 1 and Z 2 , which are each independently selected from hydrogen, CH 3 , - (CH 2 ) q CF 3 , halogen, -CONR 6 R 7 , -COOR 6 , -COR 6 , - (CH 2 ) r NR 6 R 7 ,
- (CH 2 ) r CH 3 (CH 2 ) r SOR 6 , - (CH 2 ) r SO 2 R 6 and - (CH 2 ) r SO 2 NR 6 R 7 , where R 6 and R 7 are each independently, as defined above for R 1 , and r is 0, 1 or 2;
R 1 is selected from hydrogen, methyl, ethyl, -CH 2 CH = CH 2 , -CH 2 -cyclopropyl, -CH 2 -aryl or CH 2 -heteroaryl, and the heteroaryl moieties have from 5 to 6 atoms selected from C, S , N and O;
In the case of the fenon 1 or 2 substituents independently selected from hydrogen, CH 3 , CF 3 , halogen, - (CH 2 ) q CONR 5 R 4 , - (CH 2 ) q NR 5 R 4 , - (CH 2 ) q COR 5 , - (CH 2 ) q CO 2 R 5 and -OR 5 , where q is 0 or 1, and where R 4 and R 5 are as defined above;
R 2 and R 3 each independently represents hydrogen or methyl.
R представляет морфолин, пиперидин или пирролидин
5. Соединение по п.1, которое выбирают из
и
6. Соединение по любому из предыдущих пунктов в форме его гидрохлоридной, сульфатной, тартратной или цитратной соли.4. The compound of formula (I) according to claim 1, which is
R is morpholine, piperidine or pyrrolidine
5. The compound according to claim 1, which is chosen from
and
6. The compound according to any one of the preceding paragraphs in the form of its hydrochloride, sulphate, tartrate or citrate salt.
а) взаимодействие кетона формулы (l)
где R1, R2 и R3 такие, как определено в формуле (1) в п. 1, и Х представляет уходящую группу, с металлорганическим реагентом формулы (j) или (k)
где А и В такие, как определено в формуле (I) в п. 1, и М представляет группу металла; и где взаимодействие необязательно проводят в присутствии растворителя, с получением соединения формулы (h)
где А, В, R1, R2 и R3 такие, как определено в формуле (I) в п. 1, и где R1 может быть также трет-бутоксикарбонилом;
b) дегидратацию соединения формулы (h) с получением соединения формулы (I) по п. 1.20. A method of obtaining a compound of formula (I) according to claim 1, comprising
a) the interaction of the ketone of the formula (l)
where R 1 , R 2 and R 3 are as defined in formula (1) in claim 1, and X represents a leaving group, with an organometallic reagent of formula (j) or (k)
where a and b are as defined in formula (I) in claim 1, and M represents a metal group; and where the interaction is optionally carried out in the presence of a solvent, to obtain the compounds of formula (h)
where a, b, R 1 , R 2 and R 3 such as defined in formula (I) in claim 1, and where R 1 may also be tert-butoxycarbonyl;
b) dehydrating the compound of formula (h) to obtain the compound of formula (I) in accordance with claim 1.
где А, В, R2 и R3 такие, как определено в формуле (I) в п. 1.21. The compound of the formula
where A, B, R 2 and R 3 are as defined in formula (I) in claim 1.
где R8 и R9, оба представляют этильную группу, и Z1 и Z2 такие, как определено в п. 1.22. The compound of formula (h) according to claim 21, wherein A is
where R 8 and R 9 both represent an ethyl group, and Z 1 and Z 2 are as defined in claim 1.
24. Способ лечения боли, включающий введение эффективного количества соединения формулы (I) по п. 1 субъекту, нуждающемуся в устранении боли.23. The compound according to claim 22, which is:
24. A method of treating pain, comprising administering an effective amount of a compound of formula (I) of claim 1 to a subject in need of elimination of pain.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9604785-7 | 1996-12-20 | ||
SE9604785A SE9604785D0 (en) | 1996-12-20 | 1996-12-20 | New compounds |
SE9702535-7 | 1997-07-01 | ||
SE9702535A SE9702535D0 (en) | 1997-07-01 | 1997-07-01 | New compounds |
Publications (2)
Publication Number | Publication Date |
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RU99115750A true RU99115750A (en) | 2001-05-27 |
RU2193029C2 RU2193029C2 (en) | 2002-11-20 |
Family
ID=26662830
Family Applications (1)
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RU99115750/04A RU2193029C2 (en) | 1996-12-20 | 1997-12-09 | Derivatives of piperidine, method of their synthesis, pharmaceutical composition based on thereof and intermediate compounds |
Country Status (29)
Country | Link |
---|---|
US (5) | US6187792B1 (en) |
EP (1) | EP0946511B1 (en) |
JP (1) | JP4324652B2 (en) |
KR (1) | KR100549144B1 (en) |
CN (2) | CN100519528C (en) |
AR (1) | AR010376A1 (en) |
AT (1) | ATE296288T1 (en) |
AU (1) | AU737999B2 (en) |
BR (1) | BR9714055B1 (en) |
CA (1) | CA2274074C (en) |
CZ (1) | CZ295557B6 (en) |
DE (1) | DE69733362T2 (en) |
EE (1) | EE03824B1 (en) |
ES (1) | ES2241060T3 (en) |
HK (1) | HK1022689A1 (en) |
HU (1) | HU226724B1 (en) |
ID (1) | ID22074A (en) |
IL (2) | IL130535A0 (en) |
IS (1) | IS2210B (en) |
MY (1) | MY119403A (en) |
NO (1) | NO313670B1 (en) |
NZ (1) | NZ336029A (en) |
PL (1) | PL189196B1 (en) |
PT (1) | PT946511E (en) |
RU (1) | RU2193029C2 (en) |
SK (1) | SK283211B6 (en) |
TR (1) | TR199901417T2 (en) |
TW (1) | TW548271B (en) |
WO (1) | WO1998028275A1 (en) |
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- 1997-12-08 TW TW086118465A patent/TW548271B/en not_active IP Right Cessation
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- 1997-12-09 DE DE69733362T patent/DE69733362T2/en not_active Expired - Lifetime
- 1997-12-09 US US09/029,633 patent/US6187792B1/en not_active Expired - Lifetime
- 1997-12-09 BR BRPI9714055-4A patent/BR9714055B1/en not_active IP Right Cessation
- 1997-12-09 CN CNB2004100082366A patent/CN100519528C/en not_active Expired - Fee Related
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- 1997-12-09 JP JP52866998A patent/JP4324652B2/en not_active Expired - Fee Related
- 1997-12-09 IL IL13053597A patent/IL130535A0/en active IP Right Grant
- 1997-12-09 TR TR1999/01417T patent/TR199901417T2/en unknown
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- 1997-12-09 HU HU0000610A patent/HU226724B1/en not_active IP Right Cessation
- 1997-12-09 RU RU99115750/04A patent/RU2193029C2/en not_active IP Right Cessation
- 1997-12-09 AU AU53512/98A patent/AU737999B2/en not_active Ceased
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2000
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2001
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Publication number | Priority date | Publication date | Assignee | Title |
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EA008826B1 (en) * | 2002-07-03 | 2007-08-31 | Х. Лундбекк А/С | Secondary amino anilinic piperidines as mch1 antagonists and uses thereof |
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