NO324869B1 - Piperidinderivater og legemidler inneholdende disse derivater som den aktive bestanddel - Google Patents
Piperidinderivater og legemidler inneholdende disse derivater som den aktive bestanddel Download PDFInfo
- Publication number
- NO324869B1 NO324869B1 NO20030639A NO20030639A NO324869B1 NO 324869 B1 NO324869 B1 NO 324869B1 NO 20030639 A NO20030639 A NO 20030639A NO 20030639 A NO20030639 A NO 20030639A NO 324869 B1 NO324869 B1 NO 324869B1
- Authority
- NO
- Norway
- Prior art keywords
- cyanopiperidin
- methoxyphenyl
- acetic acid
- cyclopentyloxy
- difluoromethoxyphenyl
- Prior art date
Links
- 239000004480 active ingredient Substances 0.000 title claims description 8
- 150000003053 piperidines Chemical class 0.000 title abstract description 6
- 239000003814 drug Substances 0.000 title description 2
- 229940079593 drug Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 172
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 17
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 5
- 208000010392 Bone Fractures Diseases 0.000 claims abstract description 5
- 206010012289 Dementia Diseases 0.000 claims abstract description 5
- 208000008589 Obesity Diseases 0.000 claims abstract description 5
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 5
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 5
- 206010063837 Reperfusion injury Diseases 0.000 claims abstract description 5
- 208000026935 allergic disease Diseases 0.000 claims abstract description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 5
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 5
- 208000032839 leukemia Diseases 0.000 claims abstract description 5
- 235000020824 obesity Nutrition 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 63
- -1 Piperidine derivative compound Chemical class 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 5
- 208000030507 AIDS Diseases 0.000 claims description 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
- 208000027932 Collagen disease Diseases 0.000 claims description 4
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 208000004232 Enteritis Diseases 0.000 claims description 4
- 208000011623 Obstructive Lung disease Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 208000032957 Seasonal conjunctivitis Diseases 0.000 claims description 4
- 206010040047 Sepsis Diseases 0.000 claims description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 208000006454 hepatitis Diseases 0.000 claims description 4
- 231100000283 hepatitis Toxicity 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 201000008383 nephritis Diseases 0.000 claims description 4
- 201000000306 sarcoidosis Diseases 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- NNBXOLZFXXYXCR-OAHLLOKOSA-N (2r)-2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]propanoic acid Chemical compound COC1=CC=C(C2(CCN(CC2)[C@H](C)C(O)=O)C#N)C=C1OC1CCCC1 NNBXOLZFXXYXCR-OAHLLOKOSA-N 0.000 claims description 2
- NNBXOLZFXXYXCR-HNNXBMFYSA-N (2s)-2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]propanoic acid Chemical compound COC1=CC=C(C2(CCN(CC2)[C@@H](C)C(O)=O)C#N)C=C1OC1CCCC1 NNBXOLZFXXYXCR-HNNXBMFYSA-N 0.000 claims description 2
- GPGAGSROQNIXJV-UHFFFAOYSA-N 1-[4-cyano-4-(3-cyclobutyloxy-4-methoxyphenyl)piperidin-1-yl]cyclopropane-1-carboxylic acid Chemical compound COC1=CC=C(C2(CCN(CC2)C2(CC2)C(O)=O)C#N)C=C1OC1CCC1 GPGAGSROQNIXJV-UHFFFAOYSA-N 0.000 claims description 2
- RRJPEYOSPIREFT-UHFFFAOYSA-N 1-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]cyclopropane-1-carboxylic acid Chemical compound COC1=CC=C(C2(CCN(CC2)C2(CC2)C(O)=O)C#N)C=C1OC1CCCC1 RRJPEYOSPIREFT-UHFFFAOYSA-N 0.000 claims description 2
- DWPSVKSGONOCDZ-UHFFFAOYSA-N 1-[4-cyano-4-[3-(cyclopropylmethoxy)-4-methoxyphenyl]piperidin-1-yl]cyclopropane-1-carboxylic acid Chemical compound COC1=CC=C(C2(CCN(CC2)C2(CC2)C(O)=O)C#N)C=C1OCC1CC1 DWPSVKSGONOCDZ-UHFFFAOYSA-N 0.000 claims description 2
- DQEAQOFIPOEMIZ-UHFFFAOYSA-N 2-[4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]acetic acid Chemical compound COC1=CC=C(C2CCN(CC(O)=O)CC2)C=C1OC1CCCC1 DQEAQOFIPOEMIZ-UHFFFAOYSA-N 0.000 claims description 2
- BVKPVMJIMKRJMR-UHFFFAOYSA-N 2-[4-[3-butoxy-4-(difluoromethoxy)phenyl]-4-cyanopiperidin-1-yl]acetic acid Chemical compound C1=C(OC(F)F)C(OCCCC)=CC(C2(CCN(CC(O)=O)CC2)C#N)=C1 BVKPVMJIMKRJMR-UHFFFAOYSA-N 0.000 claims description 2
- XFHBPKMBWZLCFL-UHFFFAOYSA-N 2-[4-cyano-4-(3,4-dimethoxyphenyl)piperidin-1-yl]acetic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1(C#N)CCN(CC(O)=O)CC1 XFHBPKMBWZLCFL-UHFFFAOYSA-N 0.000 claims description 2
- IERXXNPRNWKMMA-UHFFFAOYSA-N 2-[4-cyano-4-(3-cyclobutyloxy-4-methoxyphenyl)piperidin-1-yl]acetic acid Chemical compound COC1=CC=C(C2(CCN(CC(O)=O)CC2)C#N)C=C1OC1CCC1 IERXXNPRNWKMMA-UHFFFAOYSA-N 0.000 claims description 2
- YZLFGYYEKYKPMG-UHFFFAOYSA-N 2-[4-cyano-4-(3-cyclopentyloxy-4-ethoxyphenyl)piperidin-1-yl]acetic acid Chemical compound CCOC1=CC=C(C2(CCN(CC(O)=O)CC2)C#N)C=C1OC1CCCC1 YZLFGYYEKYKPMG-UHFFFAOYSA-N 0.000 claims description 2
- GCBQWJCDVWWUOJ-UHFFFAOYSA-N 2-[4-cyano-4-(3-cyclopentyloxy-4-ethoxyphenyl)piperidin-1-yl]propanoic acid Chemical compound CCOC1=CC=C(C2(CCN(CC2)C(C)C(O)=O)C#N)C=C1OC1CCCC1 GCBQWJCDVWWUOJ-UHFFFAOYSA-N 0.000 claims description 2
- GZQWHFGBCNSVIY-UHFFFAOYSA-N 2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]acetic acid Chemical compound COC1=CC=C(C2(CCN(CC(O)=O)CC2)C#N)C=C1OC1CCCC1 GZQWHFGBCNSVIY-UHFFFAOYSA-N 0.000 claims description 2
- NNBXOLZFXXYXCR-UHFFFAOYSA-N 2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]propanoic acid Chemical compound COC1=CC=C(C2(CCN(CC2)C(C)C(O)=O)C#N)C=C1OC1CCCC1 NNBXOLZFXXYXCR-UHFFFAOYSA-N 0.000 claims description 2
- FRRQGUGRTQYSGS-UHFFFAOYSA-N 2-[4-cyano-4-(3-cyclopentyloxy-4-propan-2-yloxyphenyl)piperidin-1-yl]acetic acid Chemical compound CC(C)OC1=CC=C(C2(CCN(CC(O)=O)CC2)C#N)C=C1OC1CCCC1 FRRQGUGRTQYSGS-UHFFFAOYSA-N 0.000 claims description 2
- GNGUYINVAWUFIB-UHFFFAOYSA-N 2-[4-cyano-4-(4-methoxy-3-propan-2-yloxyphenyl)piperidin-1-yl]acetic acid Chemical compound C1=C(OC(C)C)C(OC)=CC=C1C1(C#N)CCN(CC(O)=O)CC1 GNGUYINVAWUFIB-UHFFFAOYSA-N 0.000 claims description 2
- SLACRWAFJWRCAF-UHFFFAOYSA-N 2-[4-cyano-4-[3-(2,3-dihydro-1h-inden-2-yloxy)-4-methoxyphenyl]piperidin-1-yl]acetic acid Chemical compound C1=C(OC2CC3=CC=CC=C3C2)C(OC)=CC=C1C1(C#N)CCN(CC(O)=O)CC1 SLACRWAFJWRCAF-UHFFFAOYSA-N 0.000 claims description 2
- MSFUCGWQHSTLOF-UHFFFAOYSA-N 2-[4-cyano-4-[3-(cyclobutylmethoxy)-4-(difluoromethoxy)phenyl]piperidin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCC1(C#N)C1=CC=C(OC(F)F)C(OCC2CCC2)=C1 MSFUCGWQHSTLOF-UHFFFAOYSA-N 0.000 claims description 2
- LFXWMJVJHWGJBK-UHFFFAOYSA-N 2-[4-cyano-4-[3-(cyclopropylmethoxy)-4-methoxyphenyl]piperidin-1-yl]acetic acid Chemical compound COC1=CC=C(C2(CCN(CC(O)=O)CC2)C#N)C=C1OCC1CC1 LFXWMJVJHWGJBK-UHFFFAOYSA-N 0.000 claims description 2
- HPXXRDOMOCHTKD-UHFFFAOYSA-N 2-[4-cyano-4-[3-cyclobutyloxy-4-(difluoromethoxy)phenyl]piperidin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCC1(C#N)C1=CC=C(OC(F)F)C(OC2CCC2)=C1 HPXXRDOMOCHTKD-UHFFFAOYSA-N 0.000 claims description 2
- ZAKDNIWMDMDXCX-UHFFFAOYSA-N 2-[4-cyano-4-[3-cyclohexyloxy-4-(difluoromethoxy)phenyl]piperidin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCC1(C#N)C1=CC=C(OC(F)F)C(OC2CCCCC2)=C1 ZAKDNIWMDMDXCX-UHFFFAOYSA-N 0.000 claims description 2
- VSYNYAJTQPDCJZ-UHFFFAOYSA-N 2-[4-cyano-4-[3-cyclopentyloxy-4-(difluoromethoxy)phenyl]piperidin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCC1(C#N)C1=CC=C(OC(F)F)C(OC2CCCC2)=C1 VSYNYAJTQPDCJZ-UHFFFAOYSA-N 0.000 claims description 2
- KPHXMWIZEJJECW-UHFFFAOYSA-N 2-[4-cyano-4-[4-(difluoromethoxy)-3-(2,3-dihydro-1h-inden-2-yloxy)phenyl]piperidin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCC1(C#N)C1=CC=C(OC(F)F)C(OC2CC3=CC=CC=C3C2)=C1 KPHXMWIZEJJECW-UHFFFAOYSA-N 0.000 claims description 2
- GBRMONHDNOLOPL-UHFFFAOYSA-N 2-[4-cyano-4-[4-(difluoromethoxy)-3-(2-methylpropoxy)phenyl]piperidin-1-yl]acetic acid Chemical compound C1=C(OC(F)F)C(OCC(C)C)=CC(C2(CCN(CC(O)=O)CC2)C#N)=C1 GBRMONHDNOLOPL-UHFFFAOYSA-N 0.000 claims description 2
- JZVGXSSYIKGEFG-UHFFFAOYSA-N 2-[4-cyano-4-[4-(difluoromethoxy)-3-ethoxyphenyl]piperidin-1-yl]acetic acid Chemical compound C1=C(OC(F)F)C(OCC)=CC(C2(CCN(CC(O)=O)CC2)C#N)=C1 JZVGXSSYIKGEFG-UHFFFAOYSA-N 0.000 claims description 2
- BOOGVMJIEYUSAJ-UHFFFAOYSA-N 2-[4-cyano-4-[4-(difluoromethoxy)-3-propan-2-yloxyphenyl]piperidin-1-yl]acetic acid Chemical compound C1=C(OC(F)F)C(OC(C)C)=CC(C2(CCN(CC(O)=O)CC2)C#N)=C1 BOOGVMJIEYUSAJ-UHFFFAOYSA-N 0.000 claims description 2
- OPEHVEDMGPXPAB-UHFFFAOYSA-N 2-[4-cyano-4-[4-(difluoromethoxy)-3-propoxyphenyl]piperidin-1-yl]acetic acid Chemical compound C1=C(OC(F)F)C(OCCC)=CC(C2(CCN(CC(O)=O)CC2)C#N)=C1 OPEHVEDMGPXPAB-UHFFFAOYSA-N 0.000 claims description 2
- GUUFTNDJFQJMAW-UHFFFAOYSA-N 3-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]propanoic acid Chemical compound COC1=CC=C(C2(CCN(CCC(O)=O)CC2)C#N)C=C1OC1CCCC1 GUUFTNDJFQJMAW-UHFFFAOYSA-N 0.000 claims description 2
- SQYNAGQGSZCTOG-UHFFFAOYSA-N benzyl 1-[4-cyano-4-(3-cyclobutyloxy-4-methoxyphenyl)piperidin-1-yl]cyclopropane-1-carboxylate Chemical compound COC1=CC=C(C2(CCN(CC2)C2(CC2)C(=O)OCC=2C=CC=CC=2)C#N)C=C1OC1CCC1 SQYNAGQGSZCTOG-UHFFFAOYSA-N 0.000 claims description 2
- UHQNQTDSRBWTQC-UHFFFAOYSA-N benzyl 1-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]cyclopropane-1-carboxylate Chemical compound COC1=CC=C(C2(CCN(CC2)C2(CC2)C(=O)OCC=2C=CC=CC=2)C#N)C=C1OC1CCCC1 UHQNQTDSRBWTQC-UHFFFAOYSA-N 0.000 claims description 2
- XLBVNEPXGPKDAB-UHFFFAOYSA-N benzyl 1-[4-cyano-4-[3-(cyclopropylmethoxy)-4-methoxyphenyl]piperidin-1-yl]cyclopropane-1-carboxylate Chemical compound COC1=CC=C(C2(CCN(CC2)C2(CC2)C(=O)OCC=2C=CC=CC=2)C#N)C=C1OCC1CC1 XLBVNEPXGPKDAB-UHFFFAOYSA-N 0.000 claims description 2
- MNCUUYDOIJUBMH-UHFFFAOYSA-N benzyl 1-[4-cyano-4-[4-methoxy-3-(methoxymethoxy)phenyl]piperidin-1-yl]cyclopropane-1-carboxylate Chemical compound C1=C(OC)C(OCOC)=CC(C2(CCN(CC2)C2(CC2)C(=O)OCC=2C=CC=CC=2)C#N)=C1 MNCUUYDOIJUBMH-UHFFFAOYSA-N 0.000 claims description 2
- PDZIAEGUZRPCMD-UHFFFAOYSA-N benzyl 2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]-2-methylpropanoate Chemical compound COC1=CC=C(C2(CCN(CC2)C(C)(C)C(=O)OCC=2C=CC=CC=2)C#N)C=C1OC1CCCC1 PDZIAEGUZRPCMD-UHFFFAOYSA-N 0.000 claims description 2
- LEIUFQFSNLHXSJ-UHFFFAOYSA-N benzyl cyclopropanecarboxylate Chemical compound C1CC1C(=O)OCC1=CC=CC=C1 LEIUFQFSNLHXSJ-UHFFFAOYSA-N 0.000 claims description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 2
- YTYUAEVEPBZQBF-UHFFFAOYSA-N ethyl 2-[4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1C1=CC=C(OC)C(OC2CCCC2)=C1 YTYUAEVEPBZQBF-UHFFFAOYSA-N 0.000 claims description 2
- SCFFGOMSEAJQEO-UHFFFAOYSA-N ethyl 2-[4-cyano-4-(3,4-dimethoxyphenyl)piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OC)C(OC)=C1 SCFFGOMSEAJQEO-UHFFFAOYSA-N 0.000 claims description 2
- VEFBDQOKPSJEAE-UHFFFAOYSA-N ethyl 2-[4-cyano-4-(3-cyclobutyloxy-4-methoxyphenyl)piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OC)C(OC2CCC2)=C1 VEFBDQOKPSJEAE-UHFFFAOYSA-N 0.000 claims description 2
- KFTMFDMDGAEUED-UHFFFAOYSA-N ethyl 2-[4-cyano-4-(3-cyclopentyloxy-4-ethoxyphenyl)piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OCC)C(OC2CCCC2)=C1 KFTMFDMDGAEUED-UHFFFAOYSA-N 0.000 claims description 2
- UDZKODPXAGPJNK-UHFFFAOYSA-N ethyl 2-[4-cyano-4-(3-cyclopentyloxy-4-ethoxyphenyl)piperidin-1-yl]propanoate Chemical compound C1CN(C(C)C(=O)OCC)CCC1(C#N)C1=CC=C(OCC)C(OC2CCCC2)=C1 UDZKODPXAGPJNK-UHFFFAOYSA-N 0.000 claims description 2
- ZTBIBCNPNQALGN-UHFFFAOYSA-N ethyl 2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OC)C(OC2CCCC2)=C1 ZTBIBCNPNQALGN-UHFFFAOYSA-N 0.000 claims description 2
- RAOJCIRHUJBOCH-UHFFFAOYSA-N ethyl 2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]butanoate Chemical compound C1CN(C(CC)C(=O)OCC)CCC1(C#N)C1=CC=C(OC)C(OC2CCCC2)=C1 RAOJCIRHUJBOCH-UHFFFAOYSA-N 0.000 claims description 2
- IHVOICFNQVRERQ-UHFFFAOYSA-N ethyl 2-[4-cyano-4-(3-cyclopentyloxy-4-propan-2-yloxyphenyl)piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OC(C)C)C(OC2CCCC2)=C1 IHVOICFNQVRERQ-UHFFFAOYSA-N 0.000 claims description 2
- WJXDJHZARFEFCV-UHFFFAOYSA-N ethyl 2-[4-cyano-4-(3-hydroxy-4-methoxyphenyl)piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OC)C(O)=C1 WJXDJHZARFEFCV-UHFFFAOYSA-N 0.000 claims description 2
- IHQZTMYCOZQSEN-UHFFFAOYSA-N ethyl 2-[4-cyano-4-(4-methoxy-3-phenylmethoxyphenyl)piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OC)C(OCC=2C=CC=CC=2)=C1 IHQZTMYCOZQSEN-UHFFFAOYSA-N 0.000 claims description 2
- WXBLXJFLMBRNGJ-UHFFFAOYSA-N ethyl 2-[4-cyano-4-(4-methoxy-3-propan-2-yloxyphenyl)piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OC)C(OC(C)C)=C1 WXBLXJFLMBRNGJ-UHFFFAOYSA-N 0.000 claims description 2
- HKCPVZNJJBCESD-UHFFFAOYSA-N ethyl 2-[4-cyano-4-[3-(2,3-dihydro-1h-inden-2-yloxy)-4-methoxyphenyl]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OC)C(OC2CC3=CC=CC=C3C2)=C1 HKCPVZNJJBCESD-UHFFFAOYSA-N 0.000 claims description 2
- LZQXCEXSZXIRHC-UHFFFAOYSA-N ethyl 2-[4-cyano-4-[3-(cyclopropylmethoxy)-4-methoxyphenyl]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OC)C(OCC2CC2)=C1 LZQXCEXSZXIRHC-UHFFFAOYSA-N 0.000 claims description 2
- XGRPTJGEHBFTRL-UHFFFAOYSA-N ethyl 2-[4-cyano-4-[3-cyclohexyloxy-4-(difluoromethoxy)phenyl]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OC(F)F)C(OC2CCCCC2)=C1 XGRPTJGEHBFTRL-UHFFFAOYSA-N 0.000 claims description 2
- OTACKMBBROHZNZ-UHFFFAOYSA-N ethyl 2-[4-cyano-4-[3-cyclopentyloxy-4-(difluoromethoxy)phenyl]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OC(F)F)C(OC2CCCC2)=C1 OTACKMBBROHZNZ-UHFFFAOYSA-N 0.000 claims description 2
- DCKCBPWALCBJCV-UHFFFAOYSA-N ethyl 2-[4-cyano-4-[4-(difluoromethoxy)-3-propan-2-yloxyphenyl]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCC1(C#N)C1=CC=C(OC(F)F)C(OC(C)C)=C1 DCKCBPWALCBJCV-UHFFFAOYSA-N 0.000 claims description 2
- KPSJJJNLBOWSNI-UHFFFAOYSA-N ethyl 4-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]butanoate Chemical compound C1CN(CCCC(=O)OCC)CCC1(C#N)C1=CC=C(OC)C(OC2CCCC2)=C1 KPSJJJNLBOWSNI-UHFFFAOYSA-N 0.000 claims description 2
- 230000000302 ischemic effect Effects 0.000 claims description 2
- FWNOBIVWMWRZEA-MRXNPFEDSA-N methyl (2r)-2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]propanoate Chemical compound C1CN([C@H](C)C(=O)OC)CCC1(C#N)C1=CC=C(OC)C(OC2CCCC2)=C1 FWNOBIVWMWRZEA-MRXNPFEDSA-N 0.000 claims description 2
- FWNOBIVWMWRZEA-INIZCTEOSA-N methyl (2s)-2-[4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]propanoate Chemical compound C1CN([C@@H](C)C(=O)OC)CCC1(C#N)C1=CC=C(OC)C(OC2CCCC2)=C1 FWNOBIVWMWRZEA-INIZCTEOSA-N 0.000 claims description 2
- FVXHFZZZSWDYFR-UHFFFAOYSA-N methyl 2-[4-[3-butoxy-4-(difluoromethoxy)phenyl]-4-cyanopiperidin-1-yl]acetate Chemical compound C1=C(OC(F)F)C(OCCCC)=CC(C2(CCN(CC(=O)OC)CC2)C#N)=C1 FVXHFZZZSWDYFR-UHFFFAOYSA-N 0.000 claims description 2
- HTUZNUZYXFFGCQ-UHFFFAOYSA-N methyl 2-[4-cyano-4-[3-(cyclobutylmethoxy)-4-(difluoromethoxy)phenyl]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCC1(C#N)C1=CC=C(OC(F)F)C(OCC2CCC2)=C1 HTUZNUZYXFFGCQ-UHFFFAOYSA-N 0.000 claims description 2
- HGBOPKDIVFTULC-UHFFFAOYSA-N methyl 2-[4-cyano-4-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCC1(C#N)C1=CC=C(OC(F)F)C(OCC2CC2)=C1 HGBOPKDIVFTULC-UHFFFAOYSA-N 0.000 claims description 2
- BWARTZKNUXHUSL-UHFFFAOYSA-N methyl 2-[4-cyano-4-[3-cyclobutyloxy-4-(difluoromethoxy)phenyl]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCC1(C#N)C1=CC=C(OC(F)F)C(OC2CCC2)=C1 BWARTZKNUXHUSL-UHFFFAOYSA-N 0.000 claims description 2
- GPNXJLZCMUNIGG-UHFFFAOYSA-N methyl 2-[4-cyano-4-[4-(difluoromethoxy)-3-(2,3-dihydro-1h-inden-2-yloxy)phenyl]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCC1(C#N)C1=CC=C(OC(F)F)C(OC2CC3=CC=CC=C3C2)=C1 GPNXJLZCMUNIGG-UHFFFAOYSA-N 0.000 claims description 2
- DXLSQZMEIMETIO-UHFFFAOYSA-N methyl 2-[4-cyano-4-[4-(difluoromethoxy)-3-(2-methylpropoxy)phenyl]piperidin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCC1(C#N)C1=CC=C(OC(F)F)C(OCC(C)C)=C1 DXLSQZMEIMETIO-UHFFFAOYSA-N 0.000 claims description 2
- DXSFLNFRWKIWJK-UHFFFAOYSA-N methyl 2-[4-cyano-4-[4-(difluoromethoxy)-3-ethoxyphenyl]piperidin-1-yl]acetate Chemical compound C1=C(OC(F)F)C(OCC)=CC(C2(CCN(CC(=O)OC)CC2)C#N)=C1 DXSFLNFRWKIWJK-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000243881 | 2000-08-11 | ||
| JP2000357517 | 2000-11-24 | ||
| PCT/JP2001/006861 WO2002014280A1 (en) | 2000-08-11 | 2001-08-09 | Piperidine derivatives and drugs containing these derivatives as the active ingredient |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20030639D0 NO20030639D0 (no) | 2003-02-07 |
| NO20030639L NO20030639L (no) | 2003-04-09 |
| NO324869B1 true NO324869B1 (no) | 2007-12-17 |
Family
ID=26597806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20030639A NO324869B1 (no) | 2000-08-11 | 2003-02-07 | Piperidinderivater og legemidler inneholdende disse derivater som den aktive bestanddel |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US7109342B2 (cs) |
| EP (1) | EP1308440B1 (cs) |
| JP (1) | JP3433752B2 (cs) |
| KR (1) | KR100586765B1 (cs) |
| CN (1) | CN1203058C (cs) |
| AT (1) | ATE430732T1 (cs) |
| AU (2) | AU2001277738B2 (cs) |
| BR (1) | BR0113167A (cs) |
| CA (1) | CA2418313C (cs) |
| CZ (1) | CZ301834B6 (cs) |
| DE (1) | DE60138628D1 (cs) |
| ES (1) | ES2325353T3 (cs) |
| HU (1) | HUP0303673A3 (cs) |
| IL (2) | IL154231A0 (cs) |
| MX (1) | MXPA03001276A (cs) |
| NO (1) | NO324869B1 (cs) |
| NZ (1) | NZ524050A (cs) |
| PL (1) | PL205307B1 (cs) |
| RU (1) | RU2275359C2 (cs) |
| TW (1) | TWI232858B (cs) |
| WO (1) | WO2002014280A1 (cs) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20040007583A (ko) | 2001-05-23 | 2004-01-24 | 다나베 세이야꾸 가부시키가이샤 | 연골 질환의 재생치료용 조성물 |
| WO2002094321A1 (en) | 2001-05-23 | 2002-11-28 | Tanabe Seiyaku Co., Ltd. | Compositions for promoting healing of bone fracture |
| AU2003207180A1 (en) * | 2002-02-08 | 2003-09-02 | Ono Pharmaceutical Co., Ltd. | Piperidine derivative compounds and drugs containing the compounds as the active ingredient |
| DE60335788D1 (de) | 2002-02-08 | 2011-03-03 | Ono Pharmaceutical Co | Piperidinderivatverbindungen und arzneimittel, die diese verbindungen als wirkstoff enthalten |
| EP1647274A4 (en) * | 2003-07-17 | 2008-12-10 | Ono Pharmaceutical Co | REMEDY AGAINST PRURIT COMPRISING A PIPERIDINE DERIVATIVE AS AN ACTIVE INGREDIENT |
| AU2004269923B2 (en) | 2003-09-05 | 2010-05-13 | Takeda Gmbh | Use of PDE4 inhibitors for the treatment of diabetes mellitus |
| WO2005037269A1 (ja) * | 2003-10-21 | 2005-04-28 | Dainippon Sumitomo Pharma Co., Ltd. | 新規ピペリジン誘導体 |
| US20090023718A1 (en) * | 2003-11-26 | 2009-01-22 | Aton Pharma, Inc. | Diamine and Iminodiacetic Acid Hydroxamic Acid Derivatives |
| US7700626B2 (en) | 2004-06-04 | 2010-04-20 | Adolor Corporation | Compositions containing opioid antagonists |
| NZ560269A (en) | 2005-03-08 | 2010-12-24 | Nycomed Gmbh | Roflumilast for the treatment of diabetes mellitus |
| RU2008122978A (ru) | 2005-11-09 | 2009-12-20 | Комбинаторкс, Инкорпорейтед (Us) | Способы, композиции и наборы для лечения медицинских состояний |
| ES2636596T3 (es) | 2012-11-20 | 2017-10-06 | Biogen Ma Inc. | Agentes moduladores de S1P y/o ATX |
| ES2733552T3 (es) * | 2014-01-24 | 2019-11-29 | Celgene Corp | Procedimientos para el tratamiento de la obesidad mediante apremilast |
| CN113121417A (zh) * | 2019-12-30 | 2021-07-16 | 苏州盛迪亚生物医药有限公司 | 一种新型哌啶衍生物及其药物用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3195352B2 (ja) * | 1992-04-02 | 2001-08-06 | スミスクライン・ビーチャム・コーポレイション | アレルギーおよび炎症疾患の治療用化合物 |
| GB9305175D0 (en) * | 1993-03-13 | 1993-04-28 | Smithkline Beecham Plc | Novel process |
| US5459151A (en) | 1993-04-30 | 1995-10-17 | American Home Products Corporation | N-acyl substituted phenyl piperidines as bronchodilators and antiinflammatory agents |
| IL112099A (en) * | 1993-12-23 | 1999-07-14 | Ortho Pharma Corp | N-oxides of 4-arylpiperazines and 4-arylpiperidines and pharmaceutical compositions containing them |
| FR2753706B1 (fr) * | 1996-09-20 | 1998-10-30 | Nouvelles amines cycliques n-substituees, leur procede de preparation et les compositions pharmaceutiques les renfermant |
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2001
- 2001-08-09 DE DE60138628T patent/DE60138628D1/de not_active Expired - Lifetime
- 2001-08-09 JP JP2002519423A patent/JP3433752B2/ja not_active Expired - Fee Related
- 2001-08-09 IL IL15423101A patent/IL154231A0/xx unknown
- 2001-08-09 CN CNB018170099A patent/CN1203058C/zh not_active Expired - Fee Related
- 2001-08-09 PL PL361360A patent/PL205307B1/pl not_active IP Right Cessation
- 2001-08-09 AU AU2001277738A patent/AU2001277738B2/en not_active Ceased
- 2001-08-09 ES ES01955627T patent/ES2325353T3/es not_active Expired - Lifetime
- 2001-08-09 US US10/343,956 patent/US7109342B2/en not_active Expired - Fee Related
- 2001-08-09 BR BR0113167-2A patent/BR0113167A/pt active Search and Examination
- 2001-08-09 NZ NZ524050A patent/NZ524050A/en unknown
- 2001-08-09 MX MXPA03001276A patent/MXPA03001276A/es active IP Right Grant
- 2001-08-09 WO PCT/JP2001/006861 patent/WO2002014280A1/ja not_active Ceased
- 2001-08-09 TW TW090119457A patent/TWI232858B/zh not_active IP Right Cessation
- 2001-08-09 AU AU7773801A patent/AU7773801A/xx active Pending
- 2001-08-09 EP EP01955627A patent/EP1308440B1/en not_active Expired - Lifetime
- 2001-08-09 HU HU0303673A patent/HUP0303673A3/hu unknown
- 2001-08-09 CA CA002418313A patent/CA2418313C/en not_active Expired - Fee Related
- 2001-08-09 RU RU2003103853/04A patent/RU2275359C2/ru not_active IP Right Cessation
- 2001-08-09 KR KR1020037001752A patent/KR100586765B1/ko not_active Expired - Fee Related
- 2001-08-09 CZ CZ20030402A patent/CZ301834B6/cs not_active IP Right Cessation
- 2001-08-09 AT AT01955627T patent/ATE430732T1/de not_active IP Right Cessation
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2003
- 2003-01-30 IL IL154231A patent/IL154231A/en not_active IP Right Cessation
- 2003-02-07 NO NO20030639A patent/NO324869B1/no not_active IP Right Cessation
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2006
- 2006-04-12 US US11/401,846 patent/US7649095B2/en not_active Expired - Fee Related
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