JP2004508356A5 - - Google Patents
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- JP2004508356A5 JP2004508356A5 JP2002525107A JP2002525107A JP2004508356A5 JP 2004508356 A5 JP2004508356 A5 JP 2004508356A5 JP 2002525107 A JP2002525107 A JP 2002525107A JP 2002525107 A JP2002525107 A JP 2002525107A JP 2004508356 A5 JP2004508356 A5 JP 2004508356A5
- Authority
- JP
- Japan
- Prior art keywords
- cyano
- piperidin
- methyl
- cyclohexyl
- ylcarbamoyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 4-cyano-1-methyl-piperidine-4 -Ylcarbamoyl Chemical group 0.000 description 41
- 150000001875 compounds Chemical class 0.000 description 17
- 239000008194 pharmaceutical composition Substances 0.000 description 12
- TXSWHPXKIHOFFW-UHFFFAOYSA-N [n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamic acid Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC(=NC(O)=O)N1CCOCC1)CC1CCCCC1 TXSWHPXKIHOFFW-UHFFFAOYSA-N 0.000 description 6
- 229940080818 propionamide Drugs 0.000 description 5
- AUAPCPRGOMWTLP-UHFFFAOYSA-N ethyl n-[c-(3-acetamidopyrrolidin-1-yl)-n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]carbonimidoyl]carbamate Chemical compound C1CC(NC(C)=O)CN1C(NC(=O)OCC)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 AUAPCPRGOMWTLP-UHFFFAOYSA-N 0.000 description 4
- KBZKISBFIGBTRZ-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-(2,6-dimethylmorpholin-4-yl)carbonimidoyl]carbamate Chemical compound C1C(C)OC(C)CN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 KBZKISBFIGBTRZ-UHFFFAOYSA-N 0.000 description 4
- AXTPJGUZGRQXEW-UHFFFAOYSA-N (4-methoxycyclohexyl)methyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CC(OC)CCC1COC(=O)N=C(N1CCOCC1)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 AXTPJGUZGRQXEW-UHFFFAOYSA-N 0.000 description 3
- KWDFOVZJLGGFEJ-UHFFFAOYSA-N 2,2-dimethylpropyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(N=C(NC(=O)OCC(C)(C)C)N1CCOCC1)CC1CCCCC1 KWDFOVZJLGGFEJ-UHFFFAOYSA-N 0.000 description 3
- YKZKUZBOIVQPKH-UHFFFAOYSA-N 2-(2-methylpropoxy)ethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(NC(=O)OCCOCC(C)C)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 YKZKUZBOIVQPKH-UHFFFAOYSA-N 0.000 description 3
- ZZECMAPADXDGCI-UHFFFAOYSA-N 2-[(7-chloro-2-oxo-1,3-benzoxazin-4-yl)amino]-n-(4-cyano-1-propylpiperidin-4-yl)-4,4-dimethylpentanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)N=C1C(C=CC(Cl)=C2)=C2OC(=O)N1 ZZECMAPADXDGCI-UHFFFAOYSA-N 0.000 description 3
- LJQBXYJOUSGFNQ-UHFFFAOYSA-N 2-methoxyethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(NC(=O)OCCOC)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 LJQBXYJOUSGFNQ-UHFFFAOYSA-N 0.000 description 3
- QBFHFPZRNKFWFP-UHFFFAOYSA-N 2-methylpropyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(NC(=O)OCC(C)C)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 QBFHFPZRNKFWFP-UHFFFAOYSA-N 0.000 description 3
- HRIAHQGTSYVRNE-UHFFFAOYSA-N 3,3,3-trifluoropropyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(N=C(NC(=O)OCCC(F)(F)F)N1CCOCC1)CC1CCCCC1 HRIAHQGTSYVRNE-UHFFFAOYSA-N 0.000 description 3
- 208000023275 Autoimmune disease Diseases 0.000 description 3
- QMYAEYSZDOQAQU-UHFFFAOYSA-N C(#N)C1(CCN(CC1)C(C)C1=CC=CC=C1)NC(C(CC(C)(C)C)NC1=NC(OC2=C1C=CC=C2)=O)=O Chemical compound C(#N)C1(CCN(CC1)C(C)C1=CC=CC=C1)NC(C(CC(C)(C)C)NC1=NC(OC2=C1C=CC=C2)=O)=O QMYAEYSZDOQAQU-UHFFFAOYSA-N 0.000 description 3
- BKOJJWUYZWQJJJ-UHFFFAOYSA-N CN1CCC(CC1)(C#N)NCC(CCC2CCCCC2)NC3=NC(=O)OC4=C3C=CC(=C4)OC Chemical compound CN1CCC(CC1)(C#N)NCC(CCC2CCCCC2)NC3=NC(=O)OC4=C3C=CC(=C4)OC BKOJJWUYZWQJJJ-UHFFFAOYSA-N 0.000 description 3
- HVVJZHKZMVQVSX-UHFFFAOYSA-N benzyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(N=C(NC(=O)OCC=1C=CC=CC=1)N1CCOCC1)CC1CCCCC1 HVVJZHKZMVQVSX-UHFFFAOYSA-N 0.000 description 3
- QMDIUDYRGAMUOZ-UHFFFAOYSA-N cyclobutyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC(=NC(=O)OC1CCC1)N1CCOCC1)CC1CCCCC1 QMDIUDYRGAMUOZ-UHFFFAOYSA-N 0.000 description 3
- CTDYSNHNPCWMES-UHFFFAOYSA-N cyclohexyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC(=NC(=O)OC1CCCCC1)N1CCOCC1)CC1CCCCC1 CTDYSNHNPCWMES-UHFFFAOYSA-N 0.000 description 3
- VCNMFGFEKWKTOR-UHFFFAOYSA-N ethyl N-[N-[1-[(4-cyanopiperidin-4-yl)-(1-phenylethyl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-C-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C(C)OC(N=C(N1CCOCC1)NC(CC1CCCCC1)C(N(C1(CCNCC1)C#N)C(C)C1=CC=CC=C1)=O)=O VCNMFGFEKWKTOR-UHFFFAOYSA-N 0.000 description 3
- BZJDRVNKPJHZOK-UHFFFAOYSA-N ethyl n-[n-[1-[(1-benzyl-4-cyanopiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(CC=2C=CC=CC=2)CC1)C#N)CC1CCCCC1 BZJDRVNKPJHZOK-UHFFFAOYSA-N 0.000 description 3
- MYUDXAXYHFUKII-UHFFFAOYSA-N ethyl n-[n-[1-[(3-cyano-1-ethylpyrrolidin-3-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(=NC(=O)OCC)NC(C(=O)NC1(CN(CC)CC1)C#N)CC1CCCCC1 MYUDXAXYHFUKII-UHFFFAOYSA-N 0.000 description 3
- UMDIMXOSVYWGRW-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-cyclohexylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(CC1)C1CCCCC1)C#N)CC1CCCCC1 UMDIMXOSVYWGRW-UHFFFAOYSA-N 0.000 description 3
- JUISAOVTXYFCRR-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-ethylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(CC)CC1)C#N)CC1CCCCC1 JUISAOVTXYFCRR-UHFFFAOYSA-N 0.000 description 3
- FVQSHEJIJRQVTJ-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-phenylcarbonimidoyl]carbamate Chemical compound C=1C=CC=CC=1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 FVQSHEJIJRQVTJ-UHFFFAOYSA-N 0.000 description 3
- HAZFOZMOXRLOLM-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-propan-2-ylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(CC1)C(C)C)C#N)CC1CCCCC1 HAZFOZMOXRLOLM-UHFFFAOYSA-N 0.000 description 3
- ASZOKEVTNWQRHX-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-3-cycloheptyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(N=C(NC(=O)OCC)N1CCOCC1)CC1CCCCCC1 ASZOKEVTNWQRHX-UHFFFAOYSA-N 0.000 description 3
- MMXZMERDSYTTLW-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]-c-phenylcarbonimidoyl]carbamate Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=NC(=O)OCC)C1=CC=CC=C1 MMXZMERDSYTTLW-UHFFFAOYSA-N 0.000 description 3
- HWSDONNUHGFBMR-UHFFFAOYSA-N ethyl n-[n-[1-[[4-cyano-1-(cyclohexylmethyl)piperidin-4-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(CC2CCCCC2)CC1)C#N)CC1CCCCC1 HWSDONNUHGFBMR-UHFFFAOYSA-N 0.000 description 3
- KWRVDDLYAQKIMY-UHFFFAOYSA-N hexyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(NC(=O)OCCCCCC)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 KWRVDDLYAQKIMY-UHFFFAOYSA-N 0.000 description 3
- SVOLJUMFERLSGS-UHFFFAOYSA-N methyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(NC(=O)OC)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 SVOLJUMFERLSGS-UHFFFAOYSA-N 0.000 description 3
- ASAXBZDIRNRZPL-UHFFFAOYSA-N n-(1-benzyl-4-cyanopiperidin-4-yl)-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound N=1C(=O)OC=2C=CC=CC=2C=1NC(CC(C)(C)C)C(=O)NC(CC1)(C#N)CCN1CC1=CC=CC=C1 ASAXBZDIRNRZPL-UHFFFAOYSA-N 0.000 description 3
- NVNTXQLHWCUJEO-UHFFFAOYSA-N n-(1-butyl-4-cyanopiperidin-4-yl)-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound C1CN(CCCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC1=NC(=O)OC2=C1C=CC=C2 NVNTXQLHWCUJEO-UHFFFAOYSA-N 0.000 description 3
- IMGNPZFCQRLJOR-UHFFFAOYSA-N n-(4-cyano-1-ethylpiperidin-4-yl)-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound C1CN(CC)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC1=NC(=O)OC2=C1C=CC=C2 IMGNPZFCQRLJOR-UHFFFAOYSA-N 0.000 description 3
- JADQTIZWFMMUQF-UHFFFAOYSA-N n-(4-cyano-1-methylpiperidin-4-yl)-3-cyclohexyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]propanamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC=1C=2C=CC=CC=2OC(=O)N=1)CC1CCCCC1 JADQTIZWFMMUQF-UHFFFAOYSA-N 0.000 description 3
- NUISYAXZKITYMI-UHFFFAOYSA-N n-(4-cyano-1-methylpiperidin-4-yl)-3-cyclohexyl-2-[(7,8-difluoro-2-oxo-1,3-benzoxazin-4-yl)amino]propanamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC=1C=2C=CC(F)=C(F)C=2OC(=O)N=1)CC1CCCCC1 NUISYAXZKITYMI-UHFFFAOYSA-N 0.000 description 3
- CGDTZPXDMHRZBJ-UHFFFAOYSA-N n-(4-cyano-1-methylpiperidin-4-yl)-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC1=NC(=O)OC2=C1C=CC=C2 CGDTZPXDMHRZBJ-UHFFFAOYSA-N 0.000 description 3
- HAZCBXOAGZNLSM-UHFFFAOYSA-N n-(4-cyano-1-pentylpiperidin-4-yl)-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound C1CN(CCCCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC1=NC(=O)OC2=C1C=CC=C2 HAZCBXOAGZNLSM-UHFFFAOYSA-N 0.000 description 3
- VJQKOIBZPRUVSZ-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-2-[(7-fluoro-2-oxo-1,3-benzoxazin-4-yl)amino]-5,5-dimethylhexanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CCC(C)(C)C)N=C1C(C=CC(F)=C2)=C2OC(=O)N1 VJQKOIBZPRUVSZ-UHFFFAOYSA-N 0.000 description 3
- FLWOZOSPISBSRA-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-2-[(7-methoxy-2-oxo-1,3-benzoxazin-4-yl)amino]-5,5-dimethylhexanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CCC(C)(C)C)N=C1C(C=CC(OC)=C2)=C2OC(=O)N1 FLWOZOSPISBSRA-UHFFFAOYSA-N 0.000 description 3
- MOKIXBLHBYPWQU-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-3-(4,4-dimethylcyclohexyl)-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]propanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(NC=1C=2C=CC=CC=2OC(=O)N=1)CC1CCC(C)(C)CC1 MOKIXBLHBYPWQU-UHFFFAOYSA-N 0.000 description 3
- OVBGKRFWQCOJNK-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-3-cycloheptyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]propanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(N=C1C=2C=CC=CC=2OC(=O)N1)CC1CCCCCC1 OVBGKRFWQCOJNK-UHFFFAOYSA-N 0.000 description 3
- UZXJWOJKLANKLW-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-3-cyclooctyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]propanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(N=C1C=2C=CC=CC=2OC(=O)N1)CC1CCCCCCC1 UZXJWOJKLANKLW-UHFFFAOYSA-N 0.000 description 3
- UPMXGRIUMBAVEX-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-4,4-dimethyl-2-[(1-methyl-2-oxoquinazolin-4-yl)amino]pentanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC1=NC(=O)N(C)C2=CC=CC=C12 UPMXGRIUMBAVEX-UHFFFAOYSA-N 0.000 description 3
- XLCAMYPAYUKOFJ-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-4,4-dimethyl-2-[(2-oxo-1h-quinazolin-4-yl)amino]pentanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)N=C1C2=CC=CC=C2NC(=O)N1 XLCAMYPAYUKOFJ-UHFFFAOYSA-N 0.000 description 3
- CBXRWYGDRQIQME-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-5,5-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]hexanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CCC(C)(C)C)N=C1C(C=CC=C2)=C2OC(=O)N1 CBXRWYGDRQIQME-UHFFFAOYSA-N 0.000 description 3
- LAEMLWCSDHZTCA-UHFFFAOYSA-N n-[4-cyano-1-(2,2-dimethylpropyl)piperidin-4-yl]-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound N=1C(=O)OC=2C=CC=CC=2C=1NC(CC(C)(C)C)C(=O)NC1(C#N)CCN(CC(C)(C)C)CC1 LAEMLWCSDHZTCA-UHFFFAOYSA-N 0.000 description 3
- KXBXTVFTYOQEQS-UHFFFAOYSA-N n-[4-cyano-1-(3,3,3-trifluoropropyl)piperidin-4-yl]-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound N=1C(=O)OC=2C=CC=CC=2C=1NC(CC(C)(C)C)C(=O)NC1(C#N)CCN(CCC(F)(F)F)CC1 KXBXTVFTYOQEQS-UHFFFAOYSA-N 0.000 description 3
- OIOBPEVCFRKKIJ-UHFFFAOYSA-N n-[4-cyano-1-(3,3-dimethylbutyl)piperidin-4-yl]-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound C1CN(CCC(C)(C)C)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC1=NC(=O)OC2=C1C=CC=C2 OIOBPEVCFRKKIJ-UHFFFAOYSA-N 0.000 description 3
- VTSGBMMFCPIBBS-UHFFFAOYSA-N n-[4-cyano-1-[(4-fluorophenyl)methyl]piperidin-4-yl]-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound N=1C(=O)OC=2C=CC=CC=2C=1NC(CC(C)(C)C)C(=O)NC(CC1)(C#N)CCN1CC1=CC=C(F)C=C1 VTSGBMMFCPIBBS-UHFFFAOYSA-N 0.000 description 3
- NPSARFACXNWHCR-UHFFFAOYSA-N oxolan-2-ylmethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC(=NC(=O)OCC1OCCC1)N1CCOCC1)CC1CCCCC1 NPSARFACXNWHCR-UHFFFAOYSA-N 0.000 description 3
- TUEGPSRCECYDCB-UHFFFAOYSA-N oxolan-3-ylmethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC(=NC(=O)OCC1COCC1)N1CCOCC1)CC1CCCCC1 TUEGPSRCECYDCB-UHFFFAOYSA-N 0.000 description 3
- IHNHCTDCYOYYBZ-UHFFFAOYSA-N propyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(NC(=O)OCCC)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 IHNHCTDCYOYYBZ-UHFFFAOYSA-N 0.000 description 3
- ABSZKQGIRLBSQX-UHFFFAOYSA-N 2-[(6-chloro-2-oxo-1,3-benzoxazin-4-yl)amino]-n-(4-cyano-1-propylpiperidin-4-yl)-4,4-dimethylpentanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)N=C1C(C=C(Cl)C=C2)=C2OC(=O)N1 ABSZKQGIRLBSQX-UHFFFAOYSA-N 0.000 description 2
- DNLPSABETBFDMW-UHFFFAOYSA-N 2-methoxyethyl n-[n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)N=C(NC(=O)OCCOC)N1CCOCC1 DNLPSABETBFDMW-UHFFFAOYSA-N 0.000 description 2
- ZUFPZLMRWZOQOE-UHFFFAOYSA-N 3-(4-tert-butylcyclohexyl)-n-(4-cyano-1-propylpiperidin-4-yl)-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]propanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(NC=1C=2C=CC=CC=2OC(=O)N=1)CC1CCC(C(C)(C)C)CC1 ZUFPZLMRWZOQOE-UHFFFAOYSA-N 0.000 description 2
- ZMXSIRWNLOFDTM-UHFFFAOYSA-N 3-benzylsulfanyl-n-(4-cyano-1-propylpiperidin-4-yl)-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]propanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(N=C1C=2C=CC=CC=2OC(=O)N1)CSCC1=CC=CC=C1 ZMXSIRWNLOFDTM-UHFFFAOYSA-N 0.000 description 2
- ZQIPZPOBILDJOG-UHFFFAOYSA-N 3-methoxybutyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(NC(=O)OCCC(C)OC)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 ZQIPZPOBILDJOG-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- IAPYFPIPHNPFBS-UHFFFAOYSA-N CCCN(CC1)CCC1(C#N)NCC(CCC1CCCCC1)N=C(C(C=CC=C1)=C1O1)NC1=O Chemical compound CCCN(CC1)CCC1(C#N)NCC(CCC1CCCCC1)N=C(C(C=CC=C1)=C1O1)NC1=O IAPYFPIPHNPFBS-UHFFFAOYSA-N 0.000 description 2
- CYQGTGQLQUQOEK-UHFFFAOYSA-N CN1CCC(CC1)(C#N)NCC(CCC2CCCCC2)NC3=NC(=O)OC4=C3C=C(C=C4)OC Chemical compound CN1CCC(CC1)(C#N)NCC(CCC2CCCCC2)NC3=NC(=O)OC4=C3C=C(C=C4)OC CYQGTGQLQUQOEK-UHFFFAOYSA-N 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- CEBGKXMLBXOWHB-UHFFFAOYSA-N benzyl 4-cyano-4-[[3-cyclohexyl-2-[[(ethoxycarbonylamino)-morpholin-4-ylmethylidene]amino]propanoyl]amino]piperidine-1-carboxylate Chemical compound C1COCCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(CC1)C(=O)OCC=1C=CC=CC=1)C#N)CC1CCCCC1 CEBGKXMLBXOWHB-UHFFFAOYSA-N 0.000 description 2
- CFBNTIMRXJNNQH-UHFFFAOYSA-N ethyl 1-[n'-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-n-ethoxycarbonylcarbamimidoyl]piperidine-3-carboxylate Chemical compound C1CCC(C(=O)OCC)CN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 CFBNTIMRXJNNQH-UHFFFAOYSA-N 0.000 description 2
- HYWGJYQHZISBBZ-UHFFFAOYSA-N ethyl 1-[n'-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-n-ethoxycarbonylcarbamimidoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 HYWGJYQHZISBBZ-UHFFFAOYSA-N 0.000 description 2
- DTRSYXUXXDLSEB-UHFFFAOYSA-N ethyl 2-[4-[n'-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-n-ethoxycarbonylcarbamimidoyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1C(NC(=O)OCC)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 DTRSYXUXXDLSEB-UHFFFAOYSA-N 0.000 description 2
- JDSIPSCWXKWJKE-UHFFFAOYSA-N ethyl 4-[n'-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-n-ethoxycarbonylcarbamimidoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 JDSIPSCWXKWJKE-UHFFFAOYSA-N 0.000 description 2
- MDVBSHZGAIBSIX-UHFFFAOYSA-N ethyl N-[N-[1-[(4-cyanopiperidin-4-yl)-(1-phenylethyl)amino]-4,4-dimethyl-1-oxopentan-2-yl]-C-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C(C)OC(N=C(N1CCOCC1)NC(CC(C)(C)C)C(N(C1(CCNCC1)C#N)C(C)C1=CC=CC=C1)=O)=O MDVBSHZGAIBSIX-UHFFFAOYSA-N 0.000 description 2
- YGJSMTMKNPTLBY-UHFFFAOYSA-N ethyl N-[N-[1-[[3-cyano-1-(2-methylpropyl)piperidin-3-yl]amino]-4,4-dimethyl-1-oxopentan-2-yl]-C-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(NC(=O)OCC)=NC(CC(C)(C)C)C(=O)NC1(C#N)CCCN(CC(C)C)C1 YGJSMTMKNPTLBY-UHFFFAOYSA-N 0.000 description 2
- ZARYBYZMCJBBOO-UHFFFAOYSA-N ethyl n-[c-(4-acetylpiperazin-1-yl)-n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]carbonimidoyl]carbamate Chemical compound C1CN(C(C)=O)CCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 ZARYBYZMCJBBOO-UHFFFAOYSA-N 0.000 description 2
- WTHNICQEBRCWFU-UHFFFAOYSA-N ethyl n-[c-(4-carbamoylpiperidin-1-yl)-n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]carbonimidoyl]carbamate Chemical compound C1CC(C(N)=O)CCN1C(NC(=O)OCC)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 WTHNICQEBRCWFU-UHFFFAOYSA-N 0.000 description 2
- ZKNFOWFRKCRWJU-UHFFFAOYSA-N ethyl n-[c-(azepan-1-yl)-n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]carbonimidoyl]carbamate Chemical compound C1CCCCCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 ZKNFOWFRKCRWJU-UHFFFAOYSA-N 0.000 description 2
- NEMSIBSDTAURHL-UHFFFAOYSA-N ethyl n-[c-(azocan-1-yl)-n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]carbonimidoyl]carbamate Chemical compound C1CCCCCCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 NEMSIBSDTAURHL-UHFFFAOYSA-N 0.000 description 2
- WWFCGPKTNPWGOC-UHFFFAOYSA-N ethyl n-[n'-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-n,n-diethylcarbamimidoyl]carbamate Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(N=C(NC(=O)OCC)N(CC)CC)CC1CCCCC1 WWFCGPKTNPWGOC-UHFFFAOYSA-N 0.000 description 2
- VAVQUUFNYQBQEW-UHFFFAOYSA-N ethyl n-[n-[1-[(1-benzyl-4-cyanopiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(=NC(=O)OCC)NC(CC(C)(C)C)C(=O)NC(CC1)(C#N)CCN1CC1=CC=CC=C1 VAVQUUFNYQBQEW-UHFFFAOYSA-N 0.000 description 2
- UUHNRLMJKSNIQP-UHFFFAOYSA-N ethyl n-[n-[1-[(3-cyano-1-propylpyrrolidin-3-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1N(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(=NC(=O)OCC)N1CCOCC1 UUHNRLMJKSNIQP-UHFFFAOYSA-N 0.000 description 2
- HTIYHXKBYXHKGL-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-(3,3,5-trimethyl-6-azabicyclo[3.2.1]octan-6-yl)carbonimidoyl]carbamate Chemical compound C1C(CC(C)(C)C2)CC2(C)N1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 HTIYHXKBYXHKGL-UHFFFAOYSA-N 0.000 description 2
- JWWYIBHNWJBXGR-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-(3-oxopiperazin-1-yl)carbonimidoyl]carbamate Chemical compound C1CNC(=O)CN1C(NC(=O)OCC)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 JWWYIBHNWJBXGR-UHFFFAOYSA-N 0.000 description 2
- GMVNGUPYOGNBGP-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-(4-ethylpiperazin-1-yl)carbonimidoyl]carbamate Chemical compound C1CN(CC)CCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 GMVNGUPYOGNBGP-UHFFFAOYSA-N 0.000 description 2
- QMBNYJLSFJHOPM-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-(4-phenylpiperazin-1-yl)carbonimidoyl]carbamate Chemical compound C1CN(C=2C=CC=CC=2)CCN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 QMBNYJLSFJHOPM-UHFFFAOYSA-N 0.000 description 2
- LYEYZYJAQNGSGN-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-[2-(methoxymethyl)morpholin-4-yl]carbonimidoyl]carbamate Chemical compound C1COC(COC)CN1C(=NC(=O)OCC)NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 LYEYZYJAQNGSGN-UHFFFAOYSA-N 0.000 description 2
- YXXVLYHQUPLGGB-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-piperidin-1-ylcarbonimidoyl]carbamate Chemical compound C1CCCCN1C(NC(=O)OCC)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 YXXVLYHQUPLGGB-UHFFFAOYSA-N 0.000 description 2
- QTOOXYCJACWLLZ-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-pyrrolidin-1-ylcarbonimidoyl]carbamate Chemical compound C1CCCN1C(NC(=O)OCC)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 QTOOXYCJACWLLZ-UHFFFAOYSA-N 0.000 description 2
- WAPPICFWUASIMU-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-thiomorpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CSCCN1C(NC(=O)OCC)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 WAPPICFWUASIMU-UHFFFAOYSA-N 0.000 description 2
- YKCSLEBOUCIJHD-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-1-oxo-3-(3,3,5,5-tetramethylcyclohexyl)propan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(NC(=NC(=O)OCC)N1CCOCC1)CC1CC(C)(C)CC(C)(C)C1 YKCSLEBOUCIJHD-UHFFFAOYSA-N 0.000 description 2
- DOELBRAHCMEDFW-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-3-(4,4-dipropylcyclohexyl)-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(NC(=NC(=O)OCC)N1CCOCC1)CC1CCC(CCC)(CCC)CC1 DOELBRAHCMEDFW-UHFFFAOYSA-N 0.000 description 2
- FFGNSZOKJCMGJG-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-3-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(COC(C)(C)C)NC(=NC(=O)OCC)N1CCOCC1 FFGNSZOKJCMGJG-UHFFFAOYSA-N 0.000 description 2
- KUMWZAHEWBMAQH-UHFFFAOYSA-N ethyl n-[n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-3-cyclooctyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(N=C(NC(=O)OCC)N1CCOCC1)CC1CCCCCCC1 KUMWZAHEWBMAQH-UHFFFAOYSA-N 0.000 description 2
- UEFOVMJBGSNVDS-UHFFFAOYSA-N ethyl n-[n-[3-benzylsulfanyl-1-[(4-cyano-1-propylpiperidin-4-yl)amino]-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(N=C(NC(=O)OCC)N1CCOCC1)CSCC1=CC=CC=C1 UEFOVMJBGSNVDS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- NGBXODISXXIFHX-UHFFFAOYSA-N methyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(NC(=O)OC)=NC(CC(C)(C)C)C(=O)NC1(C#N)CCN(C)CC1 NGBXODISXXIFHX-UHFFFAOYSA-N 0.000 description 2
- UWNLKDNVYHSNLN-UHFFFAOYSA-N methyl n-[n-[1-[(4-cyano-1-propylpiperidin-4-yl)amino]-4,4-dimethyl-1-oxopentan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)N=C(NC(=O)OC)N1CCOCC1 UWNLKDNVYHSNLN-UHFFFAOYSA-N 0.000 description 2
- FMZRXOGESWQABI-UHFFFAOYSA-N n-(3-cyano-1-propylazepan-3-yl)-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound C1N(CCC)CCCCC1(C#N)NC(=O)C(CC(C)(C)C)NC1=NC(=O)OC2=C1C=CC=C2 FMZRXOGESWQABI-UHFFFAOYSA-N 0.000 description 2
- FPSMOQZMUJVXNP-UHFFFAOYSA-N n-(4-cyano-1-methylpiperidin-4-yl)-3-cyclohexyl-2-[(5,6-difluoro-3-oxoisoindol-1-yl)amino]propanamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(N=C1C2=CC(F)=C(F)C=C2C(=O)N1)CC1CCCCC1 FPSMOQZMUJVXNP-UHFFFAOYSA-N 0.000 description 2
- UXTHSMZOGDHDKU-UHFFFAOYSA-N n-(4-cyano-1-methylpiperidin-4-yl)-3-cyclohexyl-2-[(6-fluoro-3-oxoisoindol-1-yl)amino]propanamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(N=C1C2=CC(F)=CC=C2C(=O)N1)CC1CCCCC1 UXTHSMZOGDHDKU-UHFFFAOYSA-N 0.000 description 2
- XFLPEDATBSENFZ-UHFFFAOYSA-N n-(4-cyano-1-propylazepan-4-yl)-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound C1CN(CCC)CCCC1(C#N)NC(=O)C(CC(C)(C)C)NC1=NC(=O)OC2=C1C=CC=C2 XFLPEDATBSENFZ-UHFFFAOYSA-N 0.000 description 2
- USOBYZDUWPCVGI-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-2-[(5,6-difluoro-3-oxoisoindol-1-yl)amino]-4,4-dimethylpentanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)N=C1C2=CC(F)=C(F)C=C2C(=O)N1 USOBYZDUWPCVGI-UHFFFAOYSA-N 0.000 description 2
- VAHDZMLDOKKRSY-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-2-[(6-fluoro-3-oxoisoindol-1-yl)amino]-4,4-dimethylpentanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)N=C1C2=CC(F)=CC=C2C(=O)N1 VAHDZMLDOKKRSY-UHFFFAOYSA-N 0.000 description 2
- YXODWUCIBYZTIX-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-3-(4,4-dipropylcyclohexyl)-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]propanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(NC=1C=2C=CC=CC=2OC(=O)N=1)CC1CCC(CCC)(CCC)CC1 YXODWUCIBYZTIX-UHFFFAOYSA-N 0.000 description 2
- ORVYWDDKUPYYFO-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)N=C1C(C=CC=C2)=C2OC(=O)N1 ORVYWDDKUPYYFO-UHFFFAOYSA-N 0.000 description 2
- AIOCNIVXKFFUTL-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-4,4-dimethyl-2-[(6-methyl-2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)N=C1C(C=C(C)C=C2)=C2OC(=O)N1 AIOCNIVXKFFUTL-UHFFFAOYSA-N 0.000 description 2
- UDGBXXQVNSKHAB-UHFFFAOYSA-N n-(4-cyano-1-propylpiperidin-4-yl)-5-methyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]hexanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CCC(C)C)N=C1C(C=CC=C2)=C2OC(=O)N1 UDGBXXQVNSKHAB-UHFFFAOYSA-N 0.000 description 2
- XILQQLQZBWUMFT-UHFFFAOYSA-N n-(4-cyanopiperidin-4-yl)-4,4-dimethyl-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]pentanamide Chemical compound N=1C(=O)OC=2C=CC=CC=2C=1NC(CC(C)(C)C)C(=O)NC1(C#N)CCNCC1 XILQQLQZBWUMFT-UHFFFAOYSA-N 0.000 description 2
- NARPWKCAVBEINT-UHFFFAOYSA-N 2-[(n-benzyl-c-morpholin-4-ylcarbonimidoyl)amino]-n-(4-cyano-1-methylpiperidin-4-yl)-3-cyclohexylpropanamide Chemical compound C1CN(C)CCC1(C#N)NC(=O)C(NC(=NCC=1C=CC=CC=1)N1CCOCC1)CC1CCCCC1 NARPWKCAVBEINT-UHFFFAOYSA-N 0.000 description 1
- MFQFVBPJSJEIAP-UHFFFAOYSA-N 2-[[(4-cyanoanilino)-morpholin-4-ylmethylidene]amino]-n-(4-cyano-1-propylpiperidin-4-yl)-4,4-dimethylpentanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CC(C)(C)C)NC(N1CCOCC1)=NC1=CC=C(C#N)C=C1 MFQFVBPJSJEIAP-UHFFFAOYSA-N 0.000 description 1
- YRYXQCJESJUBJS-UHFFFAOYSA-N 2-methylpropyl n-[n-[1-[[4-cyano-1-[2-(2-methoxyethoxy)ethyl]piperidin-4-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(CCOCCOC)CCC1(C#N)NC(=O)C(NC(=NC(=O)OCC(C)C)N1CCOCC1)CC1CCCCC1 YRYXQCJESJUBJS-UHFFFAOYSA-N 0.000 description 1
- DWQKYEQZHBUQQU-UHFFFAOYSA-N 2-methylpropyl n-[n-[1-[[4-cyano-1-[3-(2-methoxyethoxy)propyl]piperidin-4-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1CN(CCCOCCOC)CCC1(C#N)NC(=O)C(NC(=NC(=O)OCC(C)C)N1CCOCC1)CC1CCCCC1 DWQKYEQZHBUQQU-UHFFFAOYSA-N 0.000 description 1
- KSTYVHMXTVVGEQ-UHFFFAOYSA-N 2-propan-2-yloxyethyl n-[n-[1-[(4-cyano-1-methylpiperidin-4-yl)amino]-3-cyclohexyl-1-oxopropan-2-yl]-c-morpholin-4-ylcarbonimidoyl]carbamate Chemical compound C1COCCN1C(NC(=O)OCCOC(C)C)=NC(C(=O)NC1(CCN(C)CC1)C#N)CC1CCCCC1 KSTYVHMXTVVGEQ-UHFFFAOYSA-N 0.000 description 1
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 1
- JXOJYAIANJCVBL-UHFFFAOYSA-N 3-tert-butylsulfanyl-n-(4-cyano-1-propylpiperidin-4-yl)-2-[(2-oxo-1,3-benzoxazin-4-yl)amino]propanamide Chemical compound C1CN(CCC)CCC1(C#N)NC(=O)C(CSC(C)(C)C)N=C1C(C=CC=C2)=C2OC(=O)N1 JXOJYAIANJCVBL-UHFFFAOYSA-N 0.000 description 1
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| PCT/US2001/008084 WO2002020485A1 (en) | 2000-09-08 | 2001-03-14 | Spiroheterocyclic nitriles useful as reversible inhibitors of cysteine proteases |
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Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9723407D0 (en) * | 1997-11-05 | 1998-01-07 | Ciba Geigy Ag | Organic compounds |
| US7704958B1 (en) * | 1999-03-05 | 2010-04-27 | Bio Holding, Inc. | Methods and compositions for inhibiting apoptosis using serine protease inhibitors |
| US6420364B1 (en) * | 1999-09-13 | 2002-07-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compound useful as reversible inhibitors of cysteine proteases |
| US6773704B1 (en) * | 1999-10-28 | 2004-08-10 | The Brigham And Women's Hospital, Inc. | Methods of treating vascular disease associated with cystatin C deficiency |
| GB0003111D0 (en) * | 2000-02-10 | 2000-03-29 | Novartis Ag | Organic compounds |
| US7030116B2 (en) | 2000-12-22 | 2006-04-18 | Aventis Pharmaceuticals Inc. | Compounds and compositions as cathepsin inhibitors |
| EP1383748A2 (en) | 2000-12-22 | 2004-01-28 | Axys Pharmaceuticals, Inc. | Novel compounds and compositions as cathepsin inhibitors |
| EP1372655B1 (en) * | 2001-03-02 | 2008-10-01 | Merck Frosst Canada Ltd. | Cathepsin cysteine protease inhibitors |
| US6982263B2 (en) * | 2001-06-08 | 2006-01-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Nitriles useful as reversible inhibitors of cysteine proteases |
| DE10141650C1 (de) * | 2001-08-24 | 2002-11-28 | Lohmann Therapie Syst Lts | Transdermales Therapeutisches System mit Fentanyl bzw. verwandten Substanzen |
| CA2460125A1 (en) | 2001-09-14 | 2003-03-27 | Aventis Pharmaceuticals Inc. | Novel compounds and compositions as cathepsin inhibitors |
| AU2002340031A1 (en) * | 2001-10-02 | 2003-04-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as reversible inhibitors of cysteine proteases |
| US6841571B2 (en) * | 2001-10-29 | 2005-01-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as reversible inhibitors of cysteine proteases |
| KR20050044497A (ko) | 2001-11-14 | 2005-05-12 | 아벤티스 파마슈티칼스 인크. | 올리고펩티드 및 카텝신 ｓ 억제제로서 이를 포함하는조성물 |
| AU2003256305A1 (en) * | 2002-06-24 | 2004-01-06 | Axys Pharmaceuticals, Inc. | Peptidic compounds as cysteine protease inhibitors |
| US7326690B2 (en) * | 2002-10-30 | 2008-02-05 | Bach Pharma, Inc. | Modulation of cell fates and activities by phthalazinediones |
| US7465745B2 (en) * | 2003-03-13 | 2008-12-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Cathepsin S inhibitors |
| US7326719B2 (en) * | 2003-03-13 | 2008-02-05 | Boehringer Ingelheim Pharmaceuticals, Inc. | Cathepsin S inhibitors |
| US7109243B2 (en) * | 2003-03-24 | 2006-09-19 | Irm Llc | Inhibitors of cathepsin S |
| US7384970B2 (en) * | 2003-03-24 | 2008-06-10 | Irm Llc | Inhibitors of cathepsin S |
| WO2004089395A2 (en) * | 2003-04-01 | 2004-10-21 | Aventis Pharmaceuticals Inc. | Use of an inhibitor of cathepsin-s or -b to treat or prevent chronic obstructive pulmonary disease |
| CA2526694A1 (en) * | 2003-06-04 | 2004-12-16 | John W. Patterson | Amidino compounds as cysteine protease inhibitors |
| US7173051B2 (en) * | 2003-06-13 | 2007-02-06 | Irm, Llc | Inhibitors of cathepsin S |
| US7256207B2 (en) * | 2003-08-20 | 2007-08-14 | Irm Llc | Inhibitors of cathepsin S |
| BRPI0410979A (pt) * | 2003-09-18 | 2006-07-04 | Axys Pharm Inc | composto, composição farmacêutica, e, métodos para tratar uma doença em um animal mediada pela catepsina s e para tratar um paciente submetido a uma terapia |
| CA2543884A1 (en) * | 2003-10-30 | 2005-05-19 | Boehringer Ingelheim Pharmaceuticals, Inc. | Dipeptide-analogue synthesis |
| UY28645A1 (es) * | 2003-12-03 | 2005-06-30 | Glaxo Group Ltd | Nuevos antagonistas del receptor muscarinico m3 de acetilcolina |
| EP1694357A1 (en) * | 2003-12-11 | 2006-08-30 | Axys Pharmaceuticals, Inc. | Use of cathepsin s inhibitors for treating an immune response caused by administration of a small molecule therapeutic or biologic |
| CN100548986C (zh) * | 2003-12-12 | 2009-10-14 | 默克弗罗斯特加拿大有限公司 | 组织蛋白酶半胱氨酸蛋白酶抑制剂 |
| JP2007516295A (ja) * | 2003-12-23 | 2007-06-21 | アクシス・ファーマシューティカルズ・インコーポレイテッド | システインプロテアーゼインヒビターとしてのアミジノ化合物 |
| EP1819667B1 (en) * | 2004-12-02 | 2012-10-17 | ViroBay, Inc. | Sulfonamide compounds as cysteine protease inhibitors |
| WO2006076797A1 (en) * | 2005-01-19 | 2006-07-27 | Merck Frosst Canada Ltd. | Cathepsin k inhibitors and atherosclerosis |
| EP1865940B1 (en) * | 2005-03-21 | 2013-02-13 | Virobay, Inc. | Alpha ketoamide compounds as cysteine protease inhibitors |
| JP5215167B2 (ja) * | 2005-03-22 | 2013-06-19 | ビロベイ，インコーポレイティド | システインプロテアーゼ阻害剤としてのスルホニル基含有化合物 |
| US7282964B2 (en) * | 2005-05-25 | 2007-10-16 | Texas Instruments Incorporated | Circuit for detecting transitions on either of two signal lines referenced at different power supply levels |
| ES2436795T3 (es) * | 2005-06-14 | 2014-01-07 | Merck Sharp & Dohme Corp. | Inhibidores heterocíclicos de aspartil proteasa, preparación y uso de los mismos |
| WO2007053499A2 (en) * | 2005-11-01 | 2007-05-10 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of ccr2 |
| US8067457B2 (en) * | 2005-11-01 | 2011-11-29 | Millennium Pharmaceuticals, Inc. | Compounds useful as antagonists of CCR2 |
| CA2628259A1 (en) | 2005-11-01 | 2007-05-10 | Janssen Pharmaceutica N.V. | Dihydroisoindolones as allosteric modulators of glucokinase |
| US20100016289A1 (en) * | 2005-11-01 | 2010-01-21 | Kevin Sprott | Compounds Useful as Antagonists of CCR2 |
| WO2007137738A1 (de) * | 2006-06-01 | 2007-12-06 | Sanofi-Aventis | Spiro-cyclische nitrile als protease-inhibitoren |
| WO2007146253A2 (en) | 2006-06-13 | 2007-12-21 | Critser John K | Methods for the cryopreservation of animal cells that contain high levels of intracellular lipids |
| US8071625B2 (en) * | 2006-08-02 | 2011-12-06 | Cytokinetics, Inc. | Certain chemical entities, compositions, and methods |
| US8063082B2 (en) * | 2006-08-02 | 2011-11-22 | Cytokinetics, Inc. | Certain chemical entities, compositions, and methods |
| CA2664878A1 (en) * | 2006-10-04 | 2008-04-10 | Virobay, Inc. | Di-fluoro containing compounds as cysteine protease inhibitors |
| US7893112B2 (en) | 2006-10-04 | 2011-02-22 | Virobay, Inc. | Di-fluoro containing compounds as cysteine protease inhibitors |
| KR100877394B1 (ko) | 2007-07-11 | 2009-01-07 | 한국화학연구원 | 카보니트릴 화합물을 포함하는 골다공증 및 치은 질환의치료 및 예방을 위한 약제학적 조성물 |
| US7897619B2 (en) | 2007-07-17 | 2011-03-01 | Amgen Inc. | Heterocyclic modulators of PKB |
| AU2008276512A1 (en) * | 2007-07-17 | 2009-01-22 | Amgen Inc. | Thiadiazole modulators of PKB |
| EP2195328A4 (en) * | 2007-08-15 | 2011-06-15 | Cytokinetics Inc | PARTICULAR CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS |
| ES2413504T3 (es) | 2007-12-21 | 2013-07-16 | Ligand Pharmaceuticals Inc. | Moduladores selectivos del receptor de andrógeno (SARM) y usos de los mismos |
| EP2719700A1 (en) | 2008-01-09 | 2014-04-16 | Amura Therapeutics Limited | Tetrahydrofuro(3,2-b)pyrrol-3-one derivatives as inhibitors of cysteine proteinases |
| CN105574346A (zh) * | 2008-09-05 | 2016-05-11 | 新基阿维罗米克斯研究公司 | 多肽偶联物与不可逆抑制剂的设计方法和检测方法 |
| EP2398320A4 (en) * | 2009-02-19 | 2012-09-19 | Univ Vanderbilt | ALLOSTERIC ANTAGONISTS OF AMIDOBIPIPERIDINECARBOXYLATE M1, ANALOGUES AND DERIVATIVES THEREOF, AND METHODS FOR THEIR MANUFACTURE AND USE |
| US8324417B2 (en) | 2009-08-19 | 2012-12-04 | Virobay, Inc. | Process for the preparation of (S)-2-amino-5-cyclopropyl-4,4-difluoropentanoic acid and alkyl esters and acid salts thereof |
| US9556426B2 (en) | 2009-09-16 | 2017-01-31 | Celgene Avilomics Research, Inc. | Protein kinase conjugates and inhibitors |
| CN102812167A (zh) | 2009-12-30 | 2012-12-05 | 阿维拉制药公司 | 蛋白的配体-介导的共价修饰 |
| WO2012151319A1 (en) | 2011-05-02 | 2012-11-08 | Virobay, Inc. | Cathepsin inhibitors for the treatment of bone cancer and bone cancer pain |
| JP5859000B2 (ja) | 2011-06-07 | 2016-02-10 | 株式会社クレハ | オキセタン化合物の製造方法、アゾリルメチルシクロペンタノール化合物の製造方法、および中間体化合物 |
| EP2537532A1 (en) | 2011-06-22 | 2012-12-26 | J. Stefan Institute | Cathepsin-binding compounds bound to a nanodevice and their diagnostic and therapeutic use |
| IN2014KN01075A (OSRAM) | 2011-11-18 | 2015-10-09 | Heptares Therapeutics Ltd | |
| CN105102424B (zh) * | 2013-01-15 | 2020-09-11 | 默克专利股份公司 | 用于治疗关节病的酰基胍类 |
| EP3613418A1 (en) | 2014-01-17 | 2020-02-26 | Ligand Pharmaceuticals, Inc. | Methods and compositions for modulating hormone levels |
| GB201404922D0 (en) | 2014-03-19 | 2014-04-30 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201513743D0 (en) | 2015-08-03 | 2015-09-16 | Heptares Therapeutics Ltd | Muscarinic agonists |
| GB201519352D0 (en) | 2015-11-02 | 2015-12-16 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| US10259787B2 (en) | 2016-10-14 | 2019-04-16 | Heptares Therapeutics Limited | Substituted cyclohexanes as muscarinic M1 receptor and/or M4 receptor agonists |
| GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
| GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819960D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| GB201819961D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| BR112021020864A2 (pt) | 2019-04-19 | 2021-12-14 | Ligand Pharm Inc | Formas cristalinas e métodos de produção de formas cristalinas de um composto |
| GB202020191D0 (en) | 2020-12-18 | 2021-02-03 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| CN111943848B (zh) * | 2020-08-19 | 2023-05-05 | 苏州旺山旺水生物医药有限公司 | 一种elexacaftor中间体的制备方法及其应用 |
Family Cites Families (171)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3467691A (en) | 1964-04-22 | 1969-09-16 | Tsutomu Irikura | N-(n-acylaminoacyl)-aminoacetonitriles |
| US6204261B1 (en) | 1995-12-20 | 2001-03-20 | Vertex Pharmaceuticals Incorporated | Inhibitors of interleukin-1β Converting enzyme inhibitors |
| JPS4310619Y1 (OSRAM) | 1967-02-16 | 1968-05-09 | ||
| EP0115472A3 (de) | 1983-01-27 | 1985-10-02 | Ciba-Geigy Ag | Pyrrolidinonderivate und Verfahren zu ihrer Herstellung |
| US4767202A (en) * | 1984-01-20 | 1988-08-30 | Minolta Camera Kabushiki Kaisha | Objective lens system for optical recording type disks |
| EP0181351A4 (en) * | 1984-05-09 | 1989-06-21 | Univ Australian | METHOD FOR MODULATING IMMUNE REACTION. |
| US4797202A (en) | 1984-09-13 | 1989-01-10 | The Dow Chemical Company | Froth flotation method |
| US4737425A (en) * | 1986-06-10 | 1988-04-12 | International Business Machines Corporation | Patterned resist and process |
| JPS6358346A (ja) | 1986-08-29 | 1988-03-14 | Fuji Photo Film Co Ltd | カラ−写真現像液組成物及びハロゲン化銀写真感光材料の処理方法 |
| US4734425A (en) | 1986-10-17 | 1988-03-29 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane substituted hydroxamic acid prostaglandin analogs |
| US4749715A (en) | 1987-03-02 | 1988-06-07 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane substituted amino prostaglandin analogs |
| FR2615104B1 (fr) | 1987-05-14 | 1989-08-18 | Centre Nat Rech Scient | Nouvelle protease de plasmodium falciparum, anticorps diriges contre cette protease, substrats peptidiques specifiques de ladite protease, et leur utilisation comme medicament contre le paludisme |
| JPS63301868A (ja) | 1987-06-01 | 1988-12-08 | Nippon Kayaku Co Ltd | Ｎ−（２−クロロイソニコチノイル）アミノ酸誘導体およびそれを有効成分とする農園芸用殺菌剤 |
| DE3719226A1 (de) | 1987-06-09 | 1988-12-22 | Bayer Ag | (2-cyan-2-oximinoacetyl)-aminosaeure-derivate |
| US4971978A (en) | 1987-09-21 | 1990-11-20 | Nadzan Alex M | Derivatives of D-glutamic acid and D-aspartic acid |
| EP0389535A1 (en) | 1987-10-26 | 1990-10-03 | Warner-Lambert Company | Renin inhibitors, processes for preparing them, methods for using them, and compositions containing them |
| US4957932A (en) | 1987-11-25 | 1990-09-18 | Merck Frosst Canada, Inc. | Benzoheterazoles |
| US4962117A (en) | 1987-11-25 | 1990-10-09 | Merck Frosst Canada, Inc. | Heterazole dialkanoic acids |
| CA1322004C (en) | 1987-11-25 | 1993-09-07 | Merck Frosst Canada Incorporated | Pyridyl styrene dialkanoic acids |
| WO1989010355A1 (en) | 1988-04-05 | 1989-11-02 | Abbott Laboratories | Derivatives of tryptophan as cck antagonists |
| US5346907A (en) | 1988-04-05 | 1994-09-13 | Abbott Laboratories | Amino acid analog CCK antagonists |
| WO1989010920A1 (en) | 1988-05-03 | 1989-11-16 | The Upjohn Company | Renin inhibitory peptides containing a substituted phenoxyacetyle group |
| DE3827727A1 (de) | 1988-08-16 | 1990-02-22 | Boehringer Ingelheim Kg | Anellierte tetrahydropyridinessigsaeurederivate, verfahren zu deren herstellung und verwendung solcher verbindungen zur kardioprotektion |
| EP0374098A3 (de) | 1988-12-15 | 1991-05-02 | Ciba-Geigy Ag | Retrovirale Proteasehemmer |
| US5270302A (en) | 1988-12-21 | 1993-12-14 | Abbott Laboratories | Derivatives of tetrapeptides as CCK agonists |
| GB8909836D0 (en) | 1989-04-28 | 1989-06-14 | Boots Co Plc | Therapeutic agent |
| US5504109A (en) | 1989-05-13 | 1996-04-02 | Bayer Aktiengesellschaft | Susbstituted amino acid amide derivatives their preparation and use |
| DE3915755A1 (de) | 1989-05-13 | 1990-11-29 | Bayer Ag | Fungizide mittel sowie substituierte aminosaeureamid-derivate und deren herstellung |
| US5196291A (en) | 1989-05-24 | 1993-03-23 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| JP2658004B2 (ja) | 1989-05-31 | 1997-09-30 | キヤノン株式会社 | 電子写真感光体 |
| JPH0462788A (ja) | 1990-06-30 | 1992-02-27 | Toshiba Corp | 電子レンジ |
| FR2665159B1 (fr) | 1990-07-24 | 1992-11-13 | Rhone Poulenc Sante | Nouveaux derives de la pyridine et de la quinoleine, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| JPH06145173A (ja) | 1990-08-21 | 1994-05-24 | Fujisawa Pharmaceut Co Ltd | １−アザビシクロ［３．２．０］ヘプト−２−エン−２−カルボン酸化合物 |
| JPH0511439A (ja) | 1990-09-13 | 1993-01-22 | Fuji Photo Film Co Ltd | 光重合性組成物 |
| DE4035961A1 (de) | 1990-11-02 | 1992-05-07 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| WO1992010675A1 (en) | 1990-12-07 | 1992-06-25 | Dyno Industrier A.S | System for utilization of wave energy |
| DE4104257A1 (de) | 1991-02-13 | 1992-08-20 | Boehringer Ingelheim Kg | Verwendung von anellierten tetrahydropyridinessigsaeurederivaten fuer die behandlung neurologischer erkrankungen |
| US5206249A (en) | 1991-03-27 | 1993-04-27 | Du Pont Merck Pharmaceutical Company | Bis-naphthalimides containing amino-acid derived linkers as anticancer agents |
| US5461176A (en) | 1991-03-27 | 1995-10-24 | The Du Pont Merck Pharmaceutical Company | Processes for preparing bis-naphthalimides containing amino-acid derived linkers |
| US5190922A (en) | 1991-06-04 | 1993-03-02 | Abbott Laboratories | Terminally modified tri-, tetra- and pentapeptide anaphylatoxin receptor ligands |
| WO1992022570A1 (en) | 1991-06-14 | 1992-12-23 | Chiron Corporation | Inhibitors of picornavirus proteases |
| US5250732A (en) | 1991-07-18 | 1993-10-05 | Genentech, Inc. | Ketamine analogues for treatment of thrombocytopenia |
| US5298377A (en) | 1991-08-28 | 1994-03-29 | Eastman Kodak Company | Photographic element with 2-equivalent magenta dye-forming coupler and filter dye |
| US5215876A (en) | 1991-08-29 | 1993-06-01 | Eastman Kodak Company | Radiographic element with uv absorbation compound in polyester support |
| US5204349A (en) | 1991-09-16 | 1993-04-20 | Merck & Co., Inc. | Amide-substituted derivatives of spiroindanylcamphorsulfonyl oxytocin antagonists |
| JP2947539B2 (ja) | 1991-11-12 | 1999-09-13 | コニカ株式会社 | ハロゲン化銀写真感光材料 |
| KR100236806B1 (ko) | 1991-12-10 | 2000-01-15 | 시오노 요시히코 | 방향족 설폰아미드계 하이드록삼산 유도체 |
| EP0547699A1 (en) | 1991-12-19 | 1993-06-23 | Merck & Co. Inc. | Peptidyl derivatives as inhibitors of interleukin-1B converting enzyme |
| GB9200209D0 (en) | 1992-01-07 | 1992-02-26 | British Bio Technology | Compounds |
| US5218123A (en) | 1992-02-18 | 1993-06-08 | Warner-Lambert Company | Didehydrotryptophan derivatives and pharmaceutical use thereof |
| US5831002A (en) | 1992-05-20 | 1998-11-03 | Basf Aktiengesellschaft | Antitumor peptides |
| JPH063787A (ja) | 1992-06-18 | 1994-01-14 | Konica Corp | ハロゲン化銀写真感光材料用固形発色現像処理剤及び該固形発色現像処理剤を用いた処理方法 |
| JPH07508513A (ja) | 1992-06-22 | 1995-09-21 | ベーリンガー インゲルハイム コマンディトゲゼルシャフト | 環化されたジヒドロピリジン及び医薬製剤の製造のためのその使用 |
| FR2694006A1 (fr) | 1992-07-22 | 1994-01-28 | Esteve Labor Dr | Amides dérivés de benzohétérocyles. |
| DE4225487A1 (de) | 1992-07-30 | 1994-02-03 | Schering Ag | Interphenylen-bicyclo(3.3.0)octan-Derivate, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung |
| JPH0651451A (ja) | 1992-07-31 | 1994-02-25 | Konica Corp | ハロゲン化銀写真感光材料用固形処理剤 |
| JP3168547B2 (ja) | 1992-08-18 | 2001-05-21 | 日本製粉株式会社 | ポテト生地用ミックス、ポテト生地の製造法およびポテト生地を用いたフライ食品 |
| JP3283114B2 (ja) | 1992-09-07 | 2002-05-20 | クミアイ化学工業株式会社 | 縮合ヘテロ環誘導体及び農園芸用殺菌剤 |
| US5389682A (en) | 1992-09-18 | 1995-02-14 | Warner-Lambert Company | Agents acting at cholecystokinin receptors |
| DE4232505A1 (de) | 1992-09-29 | 1994-03-31 | Degussa | Verfahren zur Reduktion von Carbonsäuren oder Carbonsäurederivaten sowie neue Verbindungen |
| ES2150933T3 (es) | 1992-12-22 | 2000-12-16 | Lilly Co Eli | Inhibidores de la proteasa vih utiles para el tratamiento del sida. |
| DE4303145A1 (de) | 1993-01-30 | 1994-08-04 | Schering Ag | Interphenylen-2-Oxabicyclo(2.2.1)heptan-Derivate, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung |
| JP2848232B2 (ja) | 1993-02-19 | 1999-01-20 | 武田薬品工業株式会社 | アルデヒド誘導体 |
| WO1994021657A1 (en) | 1993-03-18 | 1994-09-29 | Pfizer Inc. | Antibacterial 16-membered ring macrolides containing olefins at c-20 |
| AU6697694A (en) | 1993-03-29 | 1994-10-24 | Du Pont Merck Pharmaceutical Company, The | A process and intermediate compounds useful for the preparation of platelet glycoprotein IIb/IIIa inhibitors containing N alpha--methylarginine |
| JPH06340643A (ja) | 1993-04-04 | 1994-12-13 | Nippon Nohyaku Co Ltd | オキサゾ−ル又はチアゾ−ル誘導体及びその製造方法並びに除草剤 |
| JP3165760B2 (ja) | 1993-04-12 | 2001-05-14 | 株式会社トクヤマ | 新規化合物 |
| US5658885A (en) | 1993-04-27 | 1997-08-19 | The Dupont Merck Pharmaceutical Company | Amidino and guanidino substituted boronic acid inhibitors of trypsin-like enzymes |
| DE69406083T2 (de) | 1993-04-28 | 1998-02-26 | Ihara Chemical Ind Co | Aminosäureamide, bakterizide für gartenbau und landwirtschaft sowie herstellungverfahren |
| JPH0789951A (ja) | 1993-06-03 | 1995-04-04 | Sterling Winthrop Inc | インターロイキン−１β転換酵素阻害剤 |
| DE4321897A1 (de) | 1993-07-01 | 1995-01-12 | Hoechst Schering Agrevo Gmbh | Substituierte Aminosäureamid-Derivate, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und ihre Verwendung |
| US5514778A (en) | 1993-07-01 | 1996-05-07 | Eli Lilly And Company | Anti-picornaviral agents |
| DE4322067A1 (de) | 1993-07-02 | 1995-01-12 | Hoechst Schering Agrevo Gmbh | Acylierte Aminophenylsulfonylharnstoffe; Darstellung und Verwendung als Herbizide und Wachstumsregulatoren |
| CH686479A5 (fr) | 1993-08-11 | 1996-04-15 | Nestle Sa | Produit alimentaire a rehydratation rapide et son procede de preparation. |
| US5554753A (en) | 1993-08-25 | 1996-09-10 | Indiana University Foundation | Catalytic enantioselective synthesis of α-amino acid derivatives by phase-transfer catalysis |
| JPH07101959A (ja) | 1993-09-30 | 1995-04-18 | Sankyo Co Ltd | １−メチルカルバペネム誘導体 |
| NZ274074A (en) | 1993-10-01 | 1997-11-24 | Merrell Pharma Inc | Various dipeptide derivatives having a reduced carboxy group, the aldehyde being optionally substituted; pharmaceutical compositions |
| IT1270882B (it) | 1993-10-05 | 1997-05-13 | Isagro Srl | Oligopeptidi ad attivita' fungicida |
| JP3075657B2 (ja) | 1993-10-15 | 2000-08-14 | 富士写真フイルム株式会社 | 写真用処理組成物及び処理方法 |
| JPH09504302A (ja) | 1993-11-01 | 1997-04-28 | 日本チバガイギー株式会社 | エンドセリン・レセプター・アンタゴニスト |
| US5714484A (en) | 1993-12-08 | 1998-02-03 | Prototek, Inc. | α-(1,3-dicarbonylenol ether) methyl ketones as cysteine protease inhibitors |
| US5486623A (en) | 1993-12-08 | 1996-01-23 | Prototek, Inc. | Cysteine protease inhibitors containing heterocyclic leaving groups |
| DE4343528A1 (de) | 1993-12-16 | 1995-06-22 | Schering Ag | Zweifach heterocyclisch substituierte Benzole und Pyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| IL112759A0 (en) | 1994-02-25 | 1995-05-26 | Khepri Pharmaceuticals Inc | Novel cysteine protease inhibitors |
| PT749418E (pt) | 1994-03-10 | 2001-01-31 | Searle & Co | Derivados de l-n6-(1-iminoetil)lisina uteis como inibidores de oxido nitrico sintetase |
| ES2108504T3 (es) | 1994-03-19 | 1997-12-16 | Basf Ag | Amidas del acido carbamoiloximcarboxilico fungicidas. |
| JPH07285931A (ja) | 1994-04-19 | 1995-10-31 | Tokuyama Corp | 新規化合物 |
| DE4415049A1 (de) | 1994-04-29 | 1995-11-02 | Hoechst Schering Agrevo Gmbh | Acylierte Aminophenylsulfonylharnstoffe, Verfahren zu deren Herstellung und Verwendung als Herbizide und Wachstumsregulatoren |
| DE4419517A1 (de) | 1994-06-03 | 1995-12-07 | Basf Ag | Substituierte 3-Phenylpyrazole |
| US5847135A (en) | 1994-06-17 | 1998-12-08 | Vertex Pharmaceuticals, Incorporated | Inhibitors of interleukin-1β converting enzyme |
| US5716929A (en) | 1994-06-17 | 1998-02-10 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1β converting enzyme |
| DE4431467A1 (de) | 1994-09-03 | 1996-03-07 | Basf Ag | Caramoylcarbonsäureamide |
| CA2200981A1 (en) | 1994-10-04 | 1996-04-11 | Hisashi Takasugi | Urea derivatives and their use as acat-inhibitors |
| CN1068325C (zh) | 1994-10-26 | 2001-07-11 | 法玛西雅厄普约翰美国公司 | 苯基噁唑烷酮抗菌剂 |
| CA2163325A1 (en) | 1994-11-21 | 1996-05-22 | Kaneyoshi Kato | Amine compounds, their production and use |
| KR100383161B1 (ko) | 1994-12-02 | 2003-12-24 | 야마노우치세이야쿠 가부시키가이샤 | 신규한아미디노나프틸유도체또는이의염 |
| US5863902A (en) | 1995-01-06 | 1999-01-26 | Sibia Neurosciences, Inc. | Methods of treating neurodegenerative disorders using protease inhibitors |
| US5804560A (en) | 1995-01-06 | 1998-09-08 | Sibia Neurosciences, Inc. | Peptide and peptide analog protease inhibitors |
| US5691368A (en) | 1995-01-11 | 1997-11-25 | Hoechst Marion Roussel, Inc. | Substituted oxazolidine calpain and/or cathepsin B inhibitors |
| DE19501841A1 (de) | 1995-01-23 | 1996-07-25 | Bayer Ag | Aminosäureamide |
| DE19505932B4 (de) | 1995-02-21 | 2005-06-23 | Degussa Ag | Verfahren zur Herstellung von Oxazolidinonen, neue Oxazolidinone sowie Verwendung von Oxazolidinonen |
| US5710129A (en) | 1995-02-23 | 1998-01-20 | Ariad Pharmaceuticals, Inc. | Inhibitors of SH2-mediated processes |
| JPH08248579A (ja) | 1995-03-14 | 1996-09-27 | Mitsubishi Paper Mills Ltd | ハロゲン化銀写真感光材料及びその処理方法 |
| CZ298197A3 (cs) | 1995-03-24 | 1998-03-18 | Arris Pharmaceutical Corporation | Reverzibilní inhibitory proteas |
| US5776718A (en) * | 1995-03-24 | 1998-07-07 | Arris Pharmaceutical Corporation | Reversible protease inhibitors |
| MY114302A (en) | 1995-04-19 | 2002-09-30 | Ihara Chemical Ind Co | Benzylsulfide derivative, process for its production and pesticide |
| GB9508195D0 (en) | 1995-04-20 | 1995-06-07 | Univ British Columbia | Novel biologically active compounds and compositions,their use and derivation |
| CA2218716A1 (en) | 1995-04-21 | 1996-10-24 | Novartis Ag | N-aroylamino acid amides as endothelin inhibitors |
| JPH08319291A (ja) | 1995-05-25 | 1996-12-03 | Meiji Seika Kaisha Ltd | 新規セフェム誘導体 |
| US5756528A (en) | 1995-06-06 | 1998-05-26 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| JP3314938B2 (ja) | 1995-06-06 | 2002-08-19 | ファイザー・インコーポレーテッド | グリコーゲンホスホリラーゼ抑制剤としての置換されたｎ−（インドール−２−カルボニル）−グリシンアミド類および誘導体 |
| WO1996040753A1 (en) | 1995-06-07 | 1996-12-19 | G.D. Searle & Co. | Pipecolic acid derivatives of proline threonine amides useful for the treatment of rheumatoid arthritis |
| US6069130A (en) | 1995-06-07 | 2000-05-30 | Cor Therapeutics, Inc. | Ketoheterocyclic inhibitors of factor Xa |
| US5827860A (en) | 1995-06-07 | 1998-10-27 | Ortho Pharmaceutical Corporation | Peptidyl heterocycles useful in the treatment of thrombin related disorders |
| US5827866A (en) | 1995-06-07 | 1998-10-27 | Ortho Pharmaceutical Corporation | Peptidyl heterocycles useful in the treatment of thrombin related disorders |
| TW438591B (en) * | 1995-06-07 | 2001-06-07 | Arris Pharm Corp | Reversible cysteine protease inhibitors |
| JP2000501063A (ja) | 1995-06-29 | 2000-02-02 | メルク エンド カンパニー インコーポレーテッド | ファルネシル−タンパク質トランスフェラーゼ阻害剤の組み合わせ |
| AU6317996A (en) | 1995-07-07 | 1997-02-10 | Sagami Chemical Research Center | Peptide derivatives and angiotensin iv receptor agonist |
| GB9518552D0 (en) | 1995-09-11 | 1995-11-08 | Fujisawa Pharmaceutical Co | New heterocyclic compounds |
| US5744451A (en) | 1995-09-12 | 1998-04-28 | Warner-Lambert Company | N-substituted glutamic acid derivatives with interleukin-1 β converting enzyme inhibitory activity |
| WO1997019908A1 (en) | 1995-11-29 | 1997-06-05 | Nihon Nohyaku Co., Ltd. | Phenylalanine derivatives, optically active substances, salts or coordination compounds thereof, and their use as fungicides |
| TW474946B (en) | 1995-12-15 | 2002-02-01 | Basf Ag | Novel compounds, the preparation and use thereof |
| US5843904A (en) | 1995-12-20 | 1998-12-01 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1βconverting enzyme |
| CZ207298A3 (cs) | 1995-12-29 | 1998-11-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Fenylthiazolové deriváty, způsob výroby a farmaceutický prostředek |
| WO1997026246A1 (en) | 1996-01-16 | 1997-07-24 | Warner-Lambert Company | Substituted histidine inhibitors of protein farnesyltransferase |
| WO1997027200A1 (en) | 1996-01-26 | 1997-07-31 | Smithkline Beecham Plc | Thienoxazinone derivatives useful as antiviral agents |
| US6288037B1 (en) | 1996-01-29 | 2001-09-11 | Basf Aktiengesellschaft | Substrates and inhibitors for cysteine protease ICH-1 |
| WO1997031016A2 (en) | 1996-02-23 | 1997-08-28 | Ariad Pharmaceuticals, Inc. | New inhibitors of sh2-mediated processes |
| DE19609955A1 (de) | 1996-03-14 | 1997-09-18 | Basf Ag | Amidonitrile, Verfahren zu ihrer Herstellung, ihre Verwendung als Kaltbleichaktivatoren oder optische Aufheller in Wasch-, Reinigungs- und Bleichmitteln sowie ihre Verwendung als Ausgangsmaterial bei der Herstellung von Amidocarbonsäuren und Amidocarbonsäure-Derivaten |
| CA2204082A1 (en) | 1996-05-03 | 1997-11-03 | Michael William John Urquhart | Pharmaceutical compounds |
| DE19621483A1 (de) | 1996-05-29 | 1997-12-04 | Hoechst Ag | Substituierte 2-Naphthoylguanidine, Verfahren zur ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19621522A1 (de) | 1996-05-29 | 1997-12-04 | Hoechst Schering Agrevo Gmbh | Neue N-Acylsulfonamide, neue Mischungen aus Herbiziden und Antidots und deren Verwendung |
| DE59706319D1 (de) | 1996-05-31 | 2002-03-21 | Basf Ag | Carbamoylcarbonsäureamidoxime |
| DE19629717C1 (de) | 1996-07-25 | 1998-02-12 | Hoechst Ag | Verfahren zur katalytischen Herstellung von N-Acylglycinderivaten |
| US5939527A (en) | 1996-07-30 | 1999-08-17 | Basf Aktiengesellschaft | Tetrapeptides as antitumor agents |
| JP4205168B2 (ja) | 1996-10-02 | 2009-01-07 | ノバルティス アクチエンゲゼルシヤフト | ピリミジン誘導体およびその製造法 |
| UA79749C2 (en) | 1996-10-18 | 2007-07-25 | Vertex Pharma | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
| EP0844248B1 (de) | 1996-10-28 | 2002-07-10 | Rolic AG | Vernetzbare, photoaktive Silanderivate |
| EP0941222A2 (en) | 1996-11-12 | 1999-09-15 | Novartis AG | Pyrazole derivatives useful as herbicides |
| IL129504A0 (en) | 1996-11-22 | 2000-02-29 | Elan Pharm Inc | N-(aryl/heteroaryl/alkylacetyl) amino acid amides pharmaceutical compositions comprising same and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds |
| US5952322A (en) | 1996-12-05 | 1999-09-14 | Pfizer Inc. | Method of reducing tissue damage associated with non-cardiac ischemia using glycogen phosphorylase inhibitors |
| WO1998025617A1 (en) | 1996-12-13 | 1998-06-18 | Merck & Co., Inc. | Substituted aryl piperazines as modulators of chemokine receptor activity |
| EP1155616B1 (en) | 1996-12-19 | 2003-01-29 | ISAGRO S.p.A. | Process for the preparation of (N-phenylacetyl-N-2,6-xylil)methyl alaninate |
| DE19653647A1 (de) | 1996-12-20 | 1998-06-25 | Hoechst Ag | Vitronectin - Rezeptorantagonisten, deren Herstellung sowie deren Verwendung |
| EP0946508B1 (en) | 1996-12-23 | 2009-09-23 | Bristol-Myers Squibb Pharma Company | NITROGEN CONTAINING HETEROAROMATICS AS FACTOR Xa INHIBITORS |
| AR011164A1 (es) | 1997-02-28 | 2000-08-02 | Lilly Co Eli | Compuestos heterociclicos, composiciones farmaceuticas que los comprenden, y metodos para inhibir la liberacion del peptido beta-amiloide y/o su sintesismediante el uso de dichos compuestos |
| FR2762315B1 (fr) | 1997-04-22 | 1999-05-28 | Logeais Labor Jacques | Derives d'amino-acides inhibiteurs des metalloproteases de la matrice extracellulaire et de la liberation du tnf alpha |
| CA2288787A1 (en) | 1997-05-22 | 1998-11-26 | G.D. Searle And Co. | Pyrazole derivatives as p38 kinase inhibitors |
| EP0986382B1 (en) | 1997-05-23 | 2008-06-25 | Bayer Pharmaceuticals Corporation | Raf kinase inhibitors |
| DE1019040T1 (de) | 1997-05-23 | 2001-02-08 | Bayer Corp., West Haven | Hemmung von p38 kinase aktivität durch arylharnstoff |
| PT991625E (pt) | 1997-06-19 | 2005-10-31 | Bristol Myers Squibb Pharma Co | Inibidores de factor xa com um grupo de especificidade p1 neutro |
| ZA985247B (en) | 1997-06-19 | 1999-12-17 | Du Pont Merck Pharma | Guanidine mimics as factor Xa inhibitors. |
| EP0897908A1 (de) | 1997-08-19 | 1999-02-24 | Roche Diagnostics GmbH | 3-Aryl-Succinamido-Hydroxamsäuren, Prozesse zu ihrer Herstellung und diese Substanzen enthaltende Medikamente |
| JPH11100373A (ja) | 1997-09-26 | 1999-04-13 | Eisai Co Ltd | 新規フェノチアジン誘導体及びその医薬 |
| US5872122A (en) | 1997-10-16 | 1999-02-16 | Monsanto Company | Pyrimidinylamidino β-amino acid derivatives useful as inhibitors of platelet aggregation |
| CA2303848C (en) | 1997-10-31 | 2008-09-30 | Rhone-Poulenc Rorer Limited | Substituted anilides |
| HUP0004400A3 (en) | 1997-11-05 | 2002-10-28 | Novartis Ag | Dipeptide nitriles, process for their preparation, pharmaceutical compositions comprising thereof and their use |
| NZ505844A (en) | 1997-12-22 | 2003-10-31 | Bayer Ag | Inhibition of raf kinase using substituted heterocyclic ureas |
| PL341356A1 (en) | 1997-12-22 | 2001-04-09 | Bayer Ag | Raf kinase inhibition employing aryl- and heteroaryl-substituted heterocyclic ureas |
| IL139416A0 (en) | 1998-05-05 | 2001-11-25 | Warner Lambert Company Basf Ag | Succinamide inhibitors of interleukin-1? converting enzyme |
| AU765750B2 (en) | 1998-06-04 | 2003-09-25 | Reprogen, Inc. | Use of cathepsin s in the diagnosis and treatment of endometriosis |
| CA2360740A1 (en) | 1999-03-02 | 2000-09-08 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as reversible inhibitors of cathepsin s |
| HRP20010738B1 (en) | 1999-03-15 | 2005-02-28 | Axys Pharmaceuticals | N-cyanomethyl amides as protease inhibitors |
| KR100430981B1 (ko) * | 1999-08-10 | 2004-05-14 | 제이에프이 엔지니어링 가부시키가이샤 | 디프 드로잉성이 우수한 냉연강판의 제조방법 |
| US6420364B1 (en) * | 1999-09-13 | 2002-07-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compound useful as reversible inhibitors of cysteine proteases |
| ATE244235T1 (de) * | 1999-09-13 | 2003-07-15 | Boehringer Ingelheim Pharma | Heterocyclische verbindungen als reversible inhibitoren von cysteinproteasen |
| ATE464402T1 (de) * | 1999-09-16 | 2010-04-15 | Jfe Steel Corp | Verfahren zur herstellung einer dünnen stahlplatte mit hoher festigkeit |
| JP4265133B2 (ja) * | 1999-09-28 | 2009-05-20 | Ｊｆｅスチール株式会社 | 高張力熱延鋼板およびその製造方法 |
| EP1143019B1 (en) * | 1999-09-29 | 2014-11-26 | JFE Steel Corporation | Method for manufacturing a coiled steel sheet |
| ATE490349T1 (de) * | 1999-09-29 | 2010-12-15 | Jfe Steel Corp | Stahlblech und verfahren zu dessen herstellung |
| CN1331183A (zh) | 2000-06-28 | 2002-01-16 | 上海博德基因开发有限公司 | 一种新的多肽——人dna修复蛋白10.23和编码这种多肽的多核苷酸 |
-
2000
- 2000-09-08 US US09/655,351 patent/US6420364B1/en not_active Expired - Lifetime
-
2001
- 2001-03-14 MX MXPA03001947A patent/MXPA03001947A/es active IP Right Grant
- 2001-03-14 CN CNB018153143A patent/CN1303067C/zh not_active Expired - Fee Related
- 2001-03-14 CZ CZ2003603A patent/CZ2003603A3/cs unknown
- 2001-03-14 IL IL15408001A patent/IL154080A0/xx unknown
- 2001-03-14 US US09/808,439 patent/US6525052B2/en not_active Expired - Lifetime
- 2001-03-14 BR BR0113740-9A patent/BR0113740A/pt not_active IP Right Cessation
- 2001-03-14 KR KR10-2003-7003417A patent/KR20030051644A/ko not_active Ceased
- 2001-03-14 WO PCT/US2001/008084 patent/WO2002020485A1/en not_active Ceased
- 2001-03-14 UA UA2003042888A patent/UA73378C2/uk unknown
- 2001-03-14 EP EP01918641A patent/EP1322613A1/en not_active Withdrawn
- 2001-03-14 JP JP2002525107A patent/JP2004508356A/ja active Pending
- 2001-03-14 EE EEP200300093A patent/EE200300093A/xx unknown
- 2001-03-14 HR HR20030163A patent/HRP20030163A2/hr not_active Application Discontinuation
- 2001-03-14 AU AU2001245694A patent/AU2001245694A1/en not_active Abandoned
- 2001-03-14 YU YU17003A patent/YU17003A/sh unknown
- 2001-03-14 PL PL01361038A patent/PL361038A1/xx not_active Application Discontinuation
- 2001-03-14 CA CA002417177A patent/CA2417177A1/en not_active Abandoned
- 2001-03-14 NZ NZ525169A patent/NZ525169A/en unknown
- 2001-03-14 EA EA200300348A patent/EA005203B1/ru not_active IP Right Cessation
- 2001-03-14 SK SK286-2003A patent/SK2862003A3/sk not_active Application Discontinuation
- 2001-03-14 HU HU0303934A patent/HUP0303934A2/hu unknown
- 2001-11-02 US US10/001,134 patent/US6756372B2/en not_active Expired - Lifetime
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2002
- 2002-10-01 US US10/261,994 patent/US6787540B2/en not_active Expired - Lifetime
- 2002-10-01 US US10/261,993 patent/US6720319B2/en not_active Expired - Lifetime
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2003
- 2003-02-06 ZA ZA200301032A patent/ZA200301032B/xx unknown
- 2003-02-24 BG BG107585A patent/BG107585A/bg unknown
- 2003-03-07 NO NO20031065A patent/NO20031065L/no not_active Application Discontinuation
- 2003-04-24 US US10/422,471 patent/US7056915B2/en not_active Expired - Lifetime
- 2003-04-24 US US10/422,473 patent/US6982272B2/en not_active Expired - Lifetime
- 2003-05-29 US US10/448,698 patent/US6858623B2/en not_active Expired - Lifetime
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2004
- 2004-09-09 US US10/937,533 patent/US7265132B2/en not_active Expired - Lifetime
- 2004-09-09 US US10/937,636 patent/US7279472B2/en not_active Expired - Lifetime
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