RU96103653A - Bicyclic Tetrahydropyrazolopyridines - Google Patents
Bicyclic TetrahydropyrazolopyridinesInfo
- Publication number
- RU96103653A RU96103653A RU96103653/04A RU96103653A RU96103653A RU 96103653 A RU96103653 A RU 96103653A RU 96103653/04 A RU96103653/04 A RU 96103653/04A RU 96103653 A RU96103653 A RU 96103653A RU 96103653 A RU96103653 A RU 96103653A
- Authority
- RU
- Russia
- Prior art keywords
- ethyl
- pyrazolo
- tetrahydro
- oxo
- pyridine
- Prior art date
Links
- -1 Bicyclic Tetrahydropyrazolopyridines Chemical class 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 6
- 108010001801 Tumor Necrosis Factor-alpha Proteins 0.000 claims 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 229910005965 SO 2 Inorganic materials 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 101710031992 pRL90232 Proteins 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 101710035540 plaa2 Proteins 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 206010000565 Acquired immunodeficiency syndrome Diseases 0.000 claims 2
- 206010003246 Arthritis Diseases 0.000 claims 2
- 208000006673 Asthma Diseases 0.000 claims 2
- 206010006451 Bronchitis Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010012434 Dermatitis allergic Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 206010040070 Septic shock Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 200000000018 inflammatory disease Diseases 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 201000004681 psoriasis Diseases 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- LSARSGAQJQDEIH-UHFFFAOYSA-N 1-(1,1-dioxothiolan-3-yl)-3-ethyl-6-(3-methoxyphenyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound C1CN(C=2C=C(OC)C=CC=2)C(=O)C2=C1C(CC)=NN2C1CCS(=O)(=O)C1 LSARSGAQJQDEIH-UHFFFAOYSA-N 0.000 claims 1
- ZAKZEXHBGMZAQI-UHFFFAOYSA-N 1-(1,1-dioxothiolan-3-yl)-3-ethyl-6-[3-(trifluoromethyl)phenyl]-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound C1CN(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C2=C1C(CC)=NN2C1CCS(=O)(=O)C1 ZAKZEXHBGMZAQI-UHFFFAOYSA-N 0.000 claims 1
- JRJZYRLMEKTVEZ-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3-ethyl-6-(3-methoxyphenyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound CCC1=NN(C=2C=C(Cl)C(Cl)=CC=2)C(C2=O)=C1CCN2C1=CC=CC(OC)=C1 JRJZYRLMEKTVEZ-UHFFFAOYSA-N 0.000 claims 1
- QFTXSRCUAPWDKS-UHFFFAOYSA-N 1-cyclobutyl-3-ethyl-6-(2-methylphenyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound C1CN(C=2C(=CC=CC=2)C)C(=O)C2=C1C(CC)=NN2C1CCC1 QFTXSRCUAPWDKS-UHFFFAOYSA-N 0.000 claims 1
- ZPKXBOPRMSHUDR-UHFFFAOYSA-N 1-cyclobutyl-3-ethyl-6-(3-methoxyphenyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound C1CN(C=2C=C(OC)C=CC=2)C(=O)C2=C1C(CC)=NN2C1CCC1 ZPKXBOPRMSHUDR-UHFFFAOYSA-N 0.000 claims 1
- WJCYHKHFBFILKL-UHFFFAOYSA-N 1-cyclobutyl-3-ethyl-6-(3-methylphenyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound C1CN(C=2C=C(C)C=CC=2)C(=O)C2=C1C(CC)=NN2C1CCC1 WJCYHKHFBFILKL-UHFFFAOYSA-N 0.000 claims 1
- HRVGXJYBJMMTEJ-UHFFFAOYSA-N 1-cyclohexyl-3-ethyl-6-(3-methoxyphenyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound C1CN(C=2C=C(OC)C=CC=2)C(=O)C2=C1C(CC)=NN2C1CCCCC1 HRVGXJYBJMMTEJ-UHFFFAOYSA-N 0.000 claims 1
- IPUJXWMHZRFSAT-UHFFFAOYSA-N 1-cyclopentyl-3-ethyl-6-(2-methylphenyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound C1CN(C=2C(=CC=CC=2)C)C(=O)C2=C1C(CC)=NN2C1CCCC1 IPUJXWMHZRFSAT-UHFFFAOYSA-N 0.000 claims 1
- AUHPGOLYFSHALS-UHFFFAOYSA-N 1-cyclopentyl-3-ethyl-6-(3-methoxyphenyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound C1CN(C=2C=C(OC)C=CC=2)C(=O)C2=C1C(CC)=NN2C1CCCC1 AUHPGOLYFSHALS-UHFFFAOYSA-N 0.000 claims 1
- MEIPZRSFDUEURX-UHFFFAOYSA-N 1-cyclopentyl-3-ethyl-6-(3-methylphenyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound C1CN(C=2C=C(C)C=CC=2)C(=O)C2=C1C(CC)=NN2C1CCCC1 MEIPZRSFDUEURX-UHFFFAOYSA-N 0.000 claims 1
- MZCBWUQGZGDZAW-UHFFFAOYSA-N 1-cyclopentyl-3-ethyl-6-phenyl-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound C1CN(C=2C=CC=CC=2)C(=O)C2=C1C(CC)=NN2C1CCCC1 MZCBWUQGZGDZAW-UHFFFAOYSA-N 0.000 claims 1
- JOKXFLORDHHACQ-UHFFFAOYSA-N 1-cyclopentyl-3-ethyl-6-phenyl-5,7-dihydro-4H-pyrazolo[3,4-c]pyridine Chemical compound C1=2CN(C=3C=CC=CC=3)CCC=2C(CC)=NN1C1CCCC1 JOKXFLORDHHACQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- JLTKYAXEBNEYLW-UHFFFAOYSA-N 3-ethyl-1-(4-fluorophenyl)-6-(2-methoxyphenyl)-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound CCC1=NN(C=2C=CC(F)=CC=2)C(C2=O)=C1CCN2C1=CC=CC=C1OC JLTKYAXEBNEYLW-UHFFFAOYSA-N 0.000 claims 1
- HSUSROMNEDXTDQ-UHFFFAOYSA-N 3-ethyl-1-(4-methoxyphenyl)-6-phenyl-4,5-dihydropyrazolo[3,4-c]pyridin-7-one Chemical compound CCC1=NN(C=2C=CC(OC)=CC=2)C(C2=O)=C1CCN2C1=CC=CC=C1 HSUSROMNEDXTDQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- IDPWQLPLPLPIPB-UHFFFAOYSA-N CCc1nn(C2CCC2)c2c1CCN(C2=O)c1cccc(c1)C(F)(F)F Chemical compound CCc1nn(C2CCC2)c2c1CCN(C2=O)c1cccc(c1)C(F)(F)F IDPWQLPLPLPIPB-UHFFFAOYSA-N 0.000 claims 1
- DSBGHYAVDMZIEJ-UHFFFAOYSA-N CCc1nn(C2CCCC2)c2c1CCN(C2=O)c1cccc(c1)C(F)(F)F Chemical compound CCc1nn(C2CCCC2)c2c1CCN(C2=O)c1cccc(c1)C(F)(F)F DSBGHYAVDMZIEJ-UHFFFAOYSA-N 0.000 claims 1
- SBWOFGXAZFFFGN-UHFFFAOYSA-N COc1cccc(c1)N1CCc2c(nn(C3CCCC3)c2C1=O)C(C)C Chemical compound COc1cccc(c1)N1CCc2c(nn(C3CCCC3)c2C1=O)C(C)C SBWOFGXAZFFFGN-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000005466 alkylenyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 125000004043 oxo group 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
- 230000002265 prevention Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Claims (8)
и его фармацевтически приемлемые соли;
где R1 является водородом, (С1 - С3)-алкилом, (С3 - С5)-циклоалкилом или метилен(С3 - С5)-циклоалкилом, где каждая алкильная или алкенильная группа может быть необязательно (произвольно) замещенной вплоть до двух (С1 - С2)-алкильными или трифторметильными группами или вплоть до трех атомами галогенов;
Х является кислородом или двумя атомами водорода;
R2 и R3 каждый независимо выбираются из группы, состоящей из водорода, (С1 - С1 4)-алкильной, (С1 - С1 4)-алкоксильной, (С2 - С7)-алкенильной, (С4 - С7)-гетероциклической группы, содержащей кислород, серу, SO2 или NR5, где R5 является водородом или (С1 - С4)-алкильной или группой формулы
где а является целым числом от 1 до 5;
b и c являются 0 или 1;
R4 является водородом, гидроксилом, (С1 - С5)-алкилом, (С2 - С5)-алкенилом, (С1 - С5)-алкоксилом, (С3 - С6)-циклоалкоксилом, галогеном, трифторметилом, CO2R6, CONR6R7, NR6R7, NO2 или SO2NR6R7, где R6 и R7 каждый независимо являются водородом или (С1 - С4)-алкилом;
Z является кислородом, серой, SO2 или NR8, где R8 является водородом или (С1 - С4)-алкилом;
Y является (С1 - С5)-алкиленом или (С2 - С6)-алкенилом, произвольно замещенным вплоть до двух (С1 - С7)-алкильными или (С3 - С7)-циклоалкильными группами;
или группой формулы
где p является целым числом от 1 до 3;
W является оксогруппой или гидроксилом;
R9 является (С1 - С3)-алкилом;
где каждая указанная алкильная, алкенильная, циклоалкильная, алкоксиалкильная или гетероциклическая группа может быть произвольно замещенной от одной до четырнадцати, предпочтительно от одной до пяти, заместителями, выбранными из группы, состоящей из (С1 - С2)алкила, трифторметила или галогена,
при условии, что когда R1 является этилом и R2 является 4-метилфенилом, R3 не может быть водородом, метилом, фенилом, 4-фторфенилом или 2-пиридилом, и
при условии, что когда R2 является 4-метилфенилом и R3 является 4-фторфенилом, R1 не может быть фенилом, метилом или н-пропилом, и
при условии, что когда R1 является этилом, а R2 является фенилом, R3 не может быть 4-хлорфенилом, 4-фторфенилом или 4-метилфенилом, и
при условии, что когда R1 является этилом и R2 является 4-метоксифенилом, R3 не может быть 4-фторфенилом.1. The compound of the formula
and pharmaceutically acceptable salts thereof;
where R 1 is hydrogen, (C 1 - C 3 ) -alkyl, (C 3 - C 5 ) -cycloalkyl or methylene (C 3 - C 5 ) -cycloalkyl, where each alkyl or alkenyl group may be optionally (optionally) substituted up to two (C 1 - C 2 ) -alkyl or trifluoromethyl groups or up to three halogen atoms;
X is oxygen or two hydrogen atoms;
R 2 and R 3 are each independently selected from the group consisting of hydrogen, (C 1 - C 1 4 ) -alkyl, (C 1 - C 1 4 ) -alkoxyl, (C 2 - C 7 ) -alkenyl, (C 4 - C 7 ) -heterocyclic groups containing oxygen, sulfur, SO 2 or NR 5 , where R 5 is hydrogen or (C 1 - C 4 ) -alkyl or a group of the formula
where a is an integer from 1 to 5;
b and c are 0 or 1;
R 4 is hydrogen, hydroxyl, (C 1 - C 5 ) -alkyl, (C 2 - C 5 ) alkenyl, (C 1 - C 5 ) alkoxyl, (C 3 - C 6 ) cycloalkoxyl, halogen, trifluoromethyl , CO 2 R 6 , CONR 6 R 7 , NR 6 R 7 , NO 2 or SO 2 NR 6 R 7 , where R 6 and R 7 are each independently hydrogen or (C 1 -C 4 ) -alkyl;
Z is oxygen, sulfur, SO 2 or NR 8 , where R 8 is hydrogen or (C 1 - C 4 ) -alkyl;
Y is (C 1 - C 5 ) alkylene or (C 2 - C 6 ) alkenyl optionally substituted with up to two (C 1 - C 7 ) alkyl or (C 3 - C 7 ) cycloalkyl groups;
or a group of the formula
where p is an integer from 1 to 3;
W is an oxo group or hydroxyl;
R 9 is (C 1 - C 3 ) -alkyl;
wherein each said alkyl, alkenyl, cycloalkyl, alkoxyalkyl or heterocyclic group may be optionally substituted by one to fourteen, preferably one to five, substituents selected from the group consisting of (C 1 - C 2 ) alkyl, trifluoromethyl or halogen,
provided that when R 1 is ethyl and R 2 is 4-methylphenyl, R 3 cannot be hydrogen, methyl, phenyl, 4-fluorophenyl or 2-pyridyl, and
with the proviso that when R 2 is 4-methylphenyl and R 3 is 4-fluorophenyl, R 1 cannot be phenyl, methyl or n-propyl, and
provided that when R 1 is ethyl and R 2 is phenyl, R 3 cannot be 4-chlorophenyl, 4-fluorophenyl or 4-methylphenyl, and
provided that when R 1 is ethyl and R 2 is 4-methoxyphenyl, R 3 cannot be 4-fluorophenyl.
где а является целым числом от 1 до 5;
R4 является водородом, гидроксилом, (С1 - С5)-алкилом, (С1 - С5)-алкоксилом или галогеном.2. The compound according to claim 1, where R 1 is (C 1 - C 3 ) -alkyl and R 2 and R 3 each independently selected from the group consisting of (C 3 - C 7 ) -cycloalkyl, (C 4 - C 7 ) a heterocyclic group containing SO 2 , or a group of the formula
where a is an integer from 1 to 5;
R 4 is hydrogen, hydroxyl, (C 1 - C 5 ) -alkyl, (C 1 - C 5 ) -alkoxyl or halogen.
3-этил-1-(4- метоксифенил)-6-фенил-7- оксо-4,5,6,7-тетрагидро-1Н- пиразоло[3,4-с]пиридина;
3-этил-1- циклопентил-6-фенил-7- оксо-4,5,6,7-тетрагидро-1Н- пиразоло[3,4-с]пиридина;
3-этил-1-(3,4- дихлорфенил)-6-(3- метоксифенил)-7-оксо-4,5,6,7- тетрагидро-1Н-пиразоло [3,4-с]пиридина;
3-этил-1-циклопентил-6- (3-метоксифенил)-7-оксо-4,5,6,7- тетрагидро-1Н-пиразоло[3,4-с] пиридина;
3-этил-1-(4- фторфенил)-6-(2- метоксифенил)-7-оксо-4,5,6,7-тетрагидро-1Н- пиразоло[3,4-с]пиридина;
3-этил-1- циклопентил-6-(3-метилфенил)-7-оксо- 4,5,6,7- тетрагидро-1Н-пиразоло [3,4-с]пиридина;
3-этил-1-циклопентил-6-(3- трифторметилфенил)-7-оксо- 4,5,6,7-тетрагидро-1Н-пиразоло[3,4-с] пиридина;
3-этил-1-циклогексил-6-(3-метоксифенил)-7- оксо-4,5,6,7- тетрагидро-1Н-пиразоло [3,4-с]пиридина;
3-изопропил-1- циклопентил-6-(3- метоксифенил)-7-оксо- 4,5,6,7-тетрагидро-1Н- пиразоло[3,4-с]пиридина;
3-этил-1- циклобутил-6-(3- метоксифенил)-7-оксо-4,5,6,7-тетрагидро-1Н-пиразоло [3,4-с]пиридина;
3-этил-1- циклопентил-6-фенил-4,5,6,7- тетрагидро-1Н- пиразоло[3,4-с]пиридина;
3-этил-1- циклопентил-6-(2- метилфенил)-7-оксо-4,5,6,7- тетрагидро-1Н-пиразоло[3,4-с]пиридина;
3-этил-1-(3- сульфонил)-6-(3- метилфенил)-7-оксо-4,5,6,7- тетрагидро-1Н-пиразоло[3,4-с]пиридина;
3-этил-1-(3- сульфоланил)-6-(3- метоксифенил)-7-оксо-4,5,6,7- тетрагидро-1Н-пиразоло[3,4-с]пиридина;
3-этил-1-циклобутил-6-(3- метилфенил)-7- оксо-4,5,6,7- тетрагидро-1Н-пиразоло[3,4-с]пиридина;
3-этил-1-(3- сульфоланил)-6-(3- трифторметилфенил)-7- оксо-4,5,6,7-тетрагидро-1Н-пиразоло[3,4-с]пиридина;
3-этил-1- циклобутил-6-(3-трифторметилфенил)-7-оксо- 4,5,6,7-тетрагидро-1Н-пиразоло [3,4-с]пиридина;
3-этил-1-циклобутил-6-(2- метилфенил)-7-оксо- 4,5,6,7-тетрагидро-1Н- пиразоло[3,4-с]пиридина.4. The compound according to claim 1, selected from the group consisting of:
3-ethyl-1- (4-methoxyphenyl) -6-phenyl-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1-cyclopentyl-6-phenyl-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1- (3,4-dichlorophenyl) -6- (3-methoxyphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1-cyclopentyl-6- (3-methoxyphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1- (4-fluorophenyl) -6- (2-methoxyphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1-cyclopentyl-6- (3-methylphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1-cyclopentyl-6- (3-trifluoromethylphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1-cyclohexyl-6- (3-methoxyphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-isopropyl-1-cyclopentyl-6- (3-methoxyphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1-cyclobutyl-6- (3-methoxyphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1-cyclopentyl-6-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1-cyclopentyl-6- (2-methylphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1- (3-sulfonyl) -6- (3-methylphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1- (3-sulfolanyl) -6- (3-methoxyphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1-cyclobutyl-6- (3-methylphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1- (3-sulfolanyl) -6- (3-trifluoromethylphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1-cyclobutyl-6- (3-trifluoromethylphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine;
3-ethyl-1-cyclobutyl-6- (2-methylphenyl) -7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo [3,4-c] pyridine.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US8829293A | 1993-07-06 | 1993-07-06 | |
US08/088,292 | 1993-07-06 | ||
PCT/IB1994/000156 WO1995001980A1 (en) | 1993-07-06 | 1994-06-16 | Bicyclic tetrahydro pyrazolopyridines |
Publications (2)
Publication Number | Publication Date |
---|---|
RU96103653A true RU96103653A (en) | 1998-05-10 |
RU2131876C1 RU2131876C1 (en) | 1999-06-20 |
Family
ID=22210524
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU96103653A RU2131876C1 (en) | 1993-07-06 | 1994-06-16 | Bicyclic tetrahydropyrazolepyridines or their pharmaceutically acceptable salts, pharmaceutical composition, method of phosphodiesterase inhibition, method of patient treatment |
Country Status (20)
Country | Link |
---|---|
EP (1) | EP0707585A1 (en) |
JP (1) | JP2944048B2 (en) |
KR (1) | KR100228949B1 (en) |
CN (1) | CN1048015C (en) |
AU (1) | AU695301B2 (en) |
BR (1) | BR9406946A (en) |
CA (1) | CA2166721C (en) |
CZ (1) | CZ3696A3 (en) |
EG (1) | EG20513A (en) |
FI (1) | FI943208A (en) |
HU (1) | HUT74170A (en) |
IL (1) | IL110175A (en) |
MX (1) | MX9405132A (en) |
NO (1) | NO305029B1 (en) |
NZ (1) | NZ266525A (en) |
PL (1) | PL312426A1 (en) |
RU (1) | RU2131876C1 (en) |
TW (1) | TW316904B (en) |
WO (1) | WO1995001980A1 (en) |
ZA (1) | ZA944844B (en) |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ120097A3 (en) * | 1994-10-20 | 1998-01-14 | Pfizer Inc. | Bicyclic tetrahydropyrazolopyridines and pharmaceutical compositions based thereon |
WO1996039408A1 (en) * | 1995-06-06 | 1996-12-12 | Pfizer Inc. | TRICYCLIC 5,6-DIHYDRO-9H-PYRAZOLO[3,4-c]-1,2,4-TRIAZOLO[4,3-α]PYRIDINES |
AP932A (en) * | 1996-08-26 | 2001-02-02 | Pfizer | Tricyclic 5,6-dihydro-9H-pyrazolo (3,4c)-1,2,4,-triazolo (4,3-a) pyridines. |
KR100338610B1 (en) * | 1996-09-04 | 2002-05-27 | 디. 제이. 우드, 스피겔 알렌 제이 | Indazole Derivatives and Their Use as Inhibitors of Phosphodiesterase (PDE) type IV and the Production of Tumor Necrosis Factor (TNF) |
BR9917080A (en) | 1998-12-23 | 2002-03-12 | Du Pont Pharm Co | Compound, pharmaceutical composition, use of the compound and method of treatment or prevention of thromboembolic dysfunction |
US6858616B2 (en) | 1998-12-23 | 2005-02-22 | Bristol-Myers Squibb Pharma Company | Nitrogen containing heterobicycles as factor Xa inhibitors |
US6326495B2 (en) | 1999-04-30 | 2001-12-04 | Pfizer Inc. | Process for preparing 8-cyclopentyl-6-ethyl-3-[substituted]-5,8-dihydro-4H-1,2,3a,7,8-pentaaza-as-indacenes and intermediates useful therein |
DK1212089T3 (en) | 1999-08-21 | 2006-07-24 | Altana Pharma Ag | Synergistic combination of Roflumilast and Salmeterol |
TWI243055B (en) * | 2000-04-13 | 2005-11-11 | Nippon Zoki Pharmaceutical Co | Pharmaceutical composition for use in treatment of dermatitis |
DE60143041D1 (en) * | 2000-08-10 | 2010-10-21 | Pfizer Italia Srl | Bicyclic pyrazoles are effective as kinase inhibitors, processes for their preparation, and pharmaceutical compositions containing them |
US6960595B2 (en) * | 2001-03-23 | 2005-11-01 | Bristol-Myers Squibb Pharma Company | 5-6 to 5-7 Heterobicycles as factor Xa inhibitors |
US6750225B2 (en) | 2001-04-18 | 2004-06-15 | Bristol-Myers Squibb Pharms Company | 1,4,5,6-tetrahydropyrazolo-[3,4,-c]-pyridin-7-ones useful as factor Xa inhibitors |
EP1379244A4 (en) | 2001-04-18 | 2006-03-15 | Bristol Myers Squibb Co | 1,4,5,6-tetrahydropyrazolo- 3,4-c]-pyridin-7-ones as factor xa inhibitors |
EP1396493A4 (en) | 2001-04-26 | 2005-08-03 | Ajinomoto Kk | Heterocyclic compounds |
US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
NZ541836A (en) | 2003-02-27 | 2008-12-24 | Palau Pharma Sa | Pyrazolopyridine derivatives |
US7135469B2 (en) * | 2003-03-18 | 2006-11-14 | Bristol Myers Squibb, Co. | Linear chain substituted monocyclic and bicyclic derivatives as factor Xa inhibitors |
EP1624893A2 (en) | 2003-04-01 | 2006-02-15 | Applied Research Systems ARS Holding N.V. | Inhibitors of phosphodiesterases in infertility |
US7145012B2 (en) | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
DE102005031580A1 (en) * | 2005-07-06 | 2007-01-11 | Aicuris Gmbh & Co. Kg | Substituted sulfolanylpyrazoles and their use |
PE20081889A1 (en) * | 2007-03-23 | 2009-03-05 | Smithkline Beecham Corp | INDOL CARBOXAMIDES AS INHIBITORS OF IKK2 |
US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
CA3089569C (en) | 2007-06-04 | 2023-12-05 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
JP2011522828A (en) | 2008-06-04 | 2011-08-04 | シナジー ファーマシューティカルズ インコーポレイテッド | Guanylate cyclase agonists useful for the treatment of gastrointestinal disorders, inflammation, cancer, and other disorders |
EP2321341B1 (en) | 2008-07-16 | 2017-02-22 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
CA2828346C (en) | 2011-03-01 | 2021-01-26 | Synergy Pharmaceuticals Inc. | Process of preparing guanylate cyclase c agonists |
US9545446B2 (en) | 2013-02-25 | 2017-01-17 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
EP2970384A1 (en) | 2013-03-15 | 2016-01-20 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
US9486494B2 (en) | 2013-03-15 | 2016-11-08 | Synergy Pharmaceuticals, Inc. | Compositions useful for the treatment of gastrointestinal disorders |
JP6606491B2 (en) | 2013-06-05 | 2019-11-13 | シナジー ファーマシューティカルズ インコーポレイテッド | Ultra high purity agonist of guanylate cyclase C, method for producing and using the same |
KR20160042039A (en) | 2013-08-09 | 2016-04-18 | 알데릭스, 인코포레이티드 | Compounds and methods for inhibiting phosphate transport |
CN110357888A (en) * | 2018-04-09 | 2019-10-22 | 南京药捷安康生物科技有限公司 | Heterocycle phosphodiesterase inhibitors and application thereof |
EP3972599A1 (en) | 2019-05-21 | 2022-03-30 | Ardelyx, Inc. | Combination for lowering serum phosphate in a patient |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3365459A (en) * | 1964-09-08 | 1968-01-23 | Ciba Geigy Corp | Certain tetrahydro pyrazolo-pyridine and pyrazolo-piperidine derivatives |
FR1463883A (en) * | 1964-09-08 | 1966-07-22 | Ciba Geigy | Process for the preparation of bicyclic triaza-compounds |
US3340269A (en) * | 1964-09-08 | 1967-09-05 | Ciba Geigy Corp | 1-substituted 4-acyl-2, 3-dioxo-piperidine |
US5356897A (en) * | 1991-09-09 | 1994-10-18 | Fujisawa Pharmaceutical Co., Ltd. | 3-(heteroaryl)-pyrazololi[1,5-a]pyrimidines |
-
1994
- 1994-06-16 NZ NZ266525A patent/NZ266525A/en unknown
- 1994-06-16 EP EP94916370A patent/EP0707585A1/en not_active Withdrawn
- 1994-06-16 AU AU68057/94A patent/AU695301B2/en not_active Ceased
- 1994-06-16 KR KR1019960700019A patent/KR100228949B1/en not_active IP Right Cessation
- 1994-06-16 CN CN94193233A patent/CN1048015C/en not_active Expired - Fee Related
- 1994-06-16 JP JP7503938A patent/JP2944048B2/en not_active Expired - Lifetime
- 1994-06-16 CZ CZ9636A patent/CZ3696A3/en unknown
- 1994-06-16 WO PCT/IB1994/000156 patent/WO1995001980A1/en not_active Application Discontinuation
- 1994-06-16 HU HU9503934A patent/HUT74170A/en unknown
- 1994-06-16 BR BR9406946A patent/BR9406946A/en not_active Application Discontinuation
- 1994-06-16 CA CA002166721A patent/CA2166721C/en not_active Expired - Fee Related
- 1994-06-16 PL PL94312426A patent/PL312426A1/en unknown
- 1994-06-16 RU RU96103653A patent/RU2131876C1/en active
- 1994-06-17 TW TW083105518A patent/TW316904B/zh active
- 1994-06-30 IL IL11017594A patent/IL110175A/en active IP Right Grant
- 1994-07-05 EG EG40294A patent/EG20513A/en active
- 1994-07-05 ZA ZA944844A patent/ZA944844B/en unknown
- 1994-07-05 MX MX9405132A patent/MX9405132A/en unknown
- 1994-07-05 FI FI943208A patent/FI943208A/en unknown
-
1996
- 1996-01-05 NO NO960056A patent/NO305029B1/en unknown
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