JP2006507359A5 - - Google Patents
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- Publication number
- JP2006507359A5 JP2006507359A5 JP2005501508A JP2005501508A JP2006507359A5 JP 2006507359 A5 JP2006507359 A5 JP 2006507359A5 JP 2005501508 A JP2005501508 A JP 2005501508A JP 2005501508 A JP2005501508 A JP 2005501508A JP 2006507359 A5 JP2006507359 A5 JP 2006507359A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- medicament according
- phthalic acid
- phenoxy
- hydroxy
- 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.)
- Withdrawn
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- 239000003814 drug Substances 0.000 claims 129
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 60
- 229910052736 halogen Inorganic materials 0.000 claims 55
- 150000002367 halogens Chemical class 0.000 claims 55
- 239000001257 hydrogen Substances 0.000 claims 52
- 229910052739 hydrogen Inorganic materials 0.000 claims 52
- -1 hydroxy, mercapto Chemical group 0.000 claims 52
- 150000002431 hydrogen Chemical class 0.000 claims 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 28
- 125000000217 alkyl group Chemical group 0.000 claims 24
- 229910052757 nitrogen Inorganic materials 0.000 claims 23
- 125000001424 substituent group Chemical group 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 15
- 239000002220 antihypertensive agent Substances 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 11
- 150000003536 tetrazoles Chemical class 0.000 claims 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 11
- 208000024172 Cardiovascular disease Diseases 0.000 claims 10
- 208000019622 heart disease Diseases 0.000 claims 10
- 125000003282 alkyl amino group Chemical group 0.000 claims 9
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 9
- 125000004414 alkyl thio group Chemical group 0.000 claims 9
- 229940127088 antihypertensive drug Drugs 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 239000003795 chemical substances by application Substances 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 230000003287 optical effect Effects 0.000 claims 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 7
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 229940002612 prodrug Drugs 0.000 claims 7
- 239000000651 prodrug Substances 0.000 claims 7
- 239000005541 ACE inhibitor Substances 0.000 claims 6
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims 6
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims 6
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 6
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 6
- 239000003416 antiarrhythmic agent Substances 0.000 claims 6
- 206010003119 arrhythmia Diseases 0.000 claims 6
- 230000006793 arrhythmia Effects 0.000 claims 6
- 239000002876 beta blocker Substances 0.000 claims 6
- 125000001483 monosaccharide substituent group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 5
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 239000000332 adrenergic beta-1 receptor antagonist Substances 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 229940030600 antihypertensive agent Drugs 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 150000003949 imides Chemical class 0.000 claims 4
- 150000003053 piperidines Chemical class 0.000 claims 4
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 claims 3
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 claims 3
- OQEBIHBLFRADNM-UHFFFAOYSA-N 1,4-dideoxy-1,4-imino-d-ribitol Chemical compound OCC1NCC(O)C1O OQEBIHBLFRADNM-UHFFFAOYSA-N 0.000 claims 3
- 206010002383 Angina Pectoris Diseases 0.000 claims 3
- 206010003210 Arteriosclerosis Diseases 0.000 claims 3
- 239000002083 C09CA01 - Losartan Substances 0.000 claims 3
- 206010052337 Diastolic dysfunction Diseases 0.000 claims 3
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 claims 3
- 108010061435 Enalapril Proteins 0.000 claims 3
- 208000007530 Essential hypertension Diseases 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 3
- 206010058179 Hypertensive emergency Diseases 0.000 claims 3
- 206010022562 Intermittent claudication Diseases 0.000 claims 3
- 208000007177 Left Ventricular Hypertrophy Diseases 0.000 claims 3
- 208000034486 Multi-organ failure Diseases 0.000 claims 3
- 208000010718 Multiple Organ Failure Diseases 0.000 claims 3
- 208000021642 Muscular disease Diseases 0.000 claims 3
- 201000009623 Myopathy Diseases 0.000 claims 3
- 208000001132 Osteoporosis Diseases 0.000 claims 3
- 208000034189 Sclerosis Diseases 0.000 claims 3
- 206010071436 Systolic dysfunction Diseases 0.000 claims 3
- 230000005856 abnormality Effects 0.000 claims 3
- GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 claims 3
- 229960002122 acebutolol Drugs 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 239000003741 agents affecting lipid metabolism Substances 0.000 claims 3
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims 3
- 229940126317 angiotensin II receptor antagonist Drugs 0.000 claims 3
- 230000003288 anthiarrhythmic effect Effects 0.000 claims 3
- 230000003178 anti-diabetic effect Effects 0.000 claims 3
- 230000003579 anti-obesity Effects 0.000 claims 3
- 229940125708 antidiabetic agent Drugs 0.000 claims 3
- 239000003472 antidiabetic agent Substances 0.000 claims 3
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 3
- 210000001367 artery Anatomy 0.000 claims 3
- 229960002274 atenolol Drugs 0.000 claims 3
- 229960000830 captopril Drugs 0.000 claims 3
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical group SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 claims 3
- 230000000747 cardiac effect Effects 0.000 claims 3
- 208000029078 coronary artery disease Diseases 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 claims 3
- 229960005156 digoxin Drugs 0.000 claims 3
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 claims 3
- 229960000873 enalapril Drugs 0.000 claims 3
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 claims 3
- AQNDDEOPVVGCPG-UHFFFAOYSA-N esmolol Chemical compound COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1 AQNDDEOPVVGCPG-UHFFFAOYSA-N 0.000 claims 3
- 229960003745 esmolol Drugs 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 208000021156 intermittent vascular claudication Diseases 0.000 claims 3
- 150000002500 ions Chemical group 0.000 claims 3
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 claims 3
- 229960004773 losartan Drugs 0.000 claims 3
- 201000005857 malignant hypertension Diseases 0.000 claims 3
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical group CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims 3
- 229960003105 metformin Drugs 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims 3
- 229960002237 metoprolol Drugs 0.000 claims 3
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims 3
- 230000002107 myocardial effect Effects 0.000 claims 3
- 229960004255 nadolol Drugs 0.000 claims 3
- VWPOSFSPZNDTMJ-UCWKZMIHSA-N nadolol Chemical compound C1[C@@H](O)[C@@H](O)CC2=C1C=CC=C2OCC(O)CNC(C)(C)C VWPOSFSPZNDTMJ-UCWKZMIHSA-N 0.000 claims 3
- 230000000414 obstructive effect Effects 0.000 claims 3
- 229960002508 pindolol Drugs 0.000 claims 3
- PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 claims 3
- 230000002028 premature Effects 0.000 claims 3
- 229960003712 propranolol Drugs 0.000 claims 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 3
- 229960001455 quinapril Drugs 0.000 claims 3
- JSDRRTOADPPCHY-HSQYWUDLSA-N quinapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 JSDRRTOADPPCHY-HSQYWUDLSA-N 0.000 claims 3
- 229960003401 ramipril Drugs 0.000 claims 3
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 claims 3
- 230000033764 rhythmic process Effects 0.000 claims 3
- 229960002909 spirapril Drugs 0.000 claims 3
- 108700035424 spirapril Proteins 0.000 claims 3
- HRWCVUIFMSZDJS-SZMVWBNQSA-N spirapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2(C1)SCCS2)C(O)=O)CC1=CC=CC=C1 HRWCVUIFMSZDJS-SZMVWBNQSA-N 0.000 claims 3
- 206010042772 syncope Diseases 0.000 claims 3
- 229960004605 timolol Drugs 0.000 claims 3
- 238000002054 transplantation Methods 0.000 claims 3
- 230000035899 viability Effects 0.000 claims 3
- SPYQWYTVWZBEHS-UHFFFAOYSA-N 1-(2-hydroxyethyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OCCN1CC(O)C(O)C1CO SPYQWYTVWZBEHS-UHFFFAOYSA-N 0.000 claims 2
- OPFNZHIUHJBGEW-UHFFFAOYSA-N 1-hydroxyimidazole Chemical compound ON1C=CN=C1 OPFNZHIUHJBGEW-UHFFFAOYSA-N 0.000 claims 2
- BSNCOPOPGMQUNL-UHFFFAOYSA-N 1-hydroxytetrazole Chemical compound ON1C=NN=N1 BSNCOPOPGMQUNL-UHFFFAOYSA-N 0.000 claims 2
- GUYVHXUTASLLDR-UHFFFAOYSA-N 2-hydroxytriazole Chemical compound ON1N=CC=N1 GUYVHXUTASLLDR-UHFFFAOYSA-N 0.000 claims 2
- VRYOSYRKUMQQTL-UHFFFAOYSA-N 3-(hydroxymethyl)-5-phenylmethoxypiperidin-4-ol Chemical compound OC1C(CO)CNCC1OCC1=CC=CC=C1 VRYOSYRKUMQQTL-UHFFFAOYSA-N 0.000 claims 2
- QPYJXFZUIJOGNX-UHFFFAOYSA-N 5-(hydroxymethyl)piperidine-3,4-diol Chemical compound OCC1CNCC(O)C1O QPYJXFZUIJOGNX-UHFFFAOYSA-N 0.000 claims 2
- WPRCMXASRHJGNG-UHFFFAOYSA-N 5-methylpiperidine-3,4-diol Chemical compound CC1CNCC(O)C1O WPRCMXASRHJGNG-UHFFFAOYSA-N 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 101100240526 Caenorhabditis elegans nhr-20 gene Proteins 0.000 claims 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 claims 2
- 206010038563 Reocclusion Diseases 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- QPYJXFZUIJOGNX-HSUXUTPPSA-N afegostat Chemical compound OC[C@H]1CNC[C@@H](O)[C@@H]1O QPYJXFZUIJOGNX-HSUXUTPPSA-N 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 230000036772 blood pressure Effects 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- RNSKZOAZKGPNNU-BWZBUEFSSA-N (2r,3r,4r)-1-(1,3-dihydroxypropan-2-yl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OCC(CO)N1C[C@@H](O)[C@H](O)[C@H]1CO RNSKZOAZKGPNNU-BWZBUEFSSA-N 0.000 claims 1
- FAACDRZBXLTQDQ-UIYHXYAWSA-N (2r,3r,4r)-1-(2,3-dihydroxypropyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OCC(O)CN1C[C@@H](O)[C@H](O)[C@H]1CO FAACDRZBXLTQDQ-UIYHXYAWSA-N 0.000 claims 1
- UHFWEDDFLFAJHG-FSDSQADBSA-N (2r,3r,4r)-1-(2-aminoethyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound NCCN1C[C@@H](O)[C@H](O)[C@H]1CO UHFWEDDFLFAJHG-FSDSQADBSA-N 0.000 claims 1
- SPYQWYTVWZBEHS-FSDSQADBSA-N (2r,3r,4r)-1-(2-hydroxyethyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OCCN1C[C@@H](O)[C@H](O)[C@H]1CO SPYQWYTVWZBEHS-FSDSQADBSA-N 0.000 claims 1
- SPPKZKQXTFBLLK-IWSPIJDZSA-N (2r,3r,4r)-1-(cyclopropylmethyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OC[C@@H]1[C@@H](O)[C@H](O)CN1CC1CC1 SPPKZKQXTFBLLK-IWSPIJDZSA-N 0.000 claims 1
- SBDAWMSBMQBJRA-IJLUTSLNSA-N (2r,3r,4r)-1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OC[C@@H]1[C@@H](O)[C@H](O)CN1CC1=CC=CC=C1 SBDAWMSBMQBJRA-IJLUTSLNSA-N 0.000 claims 1
- AORXTDSJOOFVRB-IWSPIJDZSA-N (2r,3r,4r)-1-butyl-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound CCCCN1C[C@@H](O)[C@H](O)[C@H]1CO AORXTDSJOOFVRB-IWSPIJDZSA-N 0.000 claims 1
- ITBZTMURQMEUAL-HSUXUTPPSA-N (2r,3r,4r)-2-(hydroxymethyl)-1-(2,2,2-trifluoroethyl)pyrrolidine-3,4-diol Chemical compound OC[C@@H]1[C@@H](O)[C@H](O)CN1CC(F)(F)F ITBZTMURQMEUAL-HSUXUTPPSA-N 0.000 claims 1
- UBVOJPDDTVFNFJ-HSUXUTPPSA-N (2r,3r,4r)-2-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol Chemical compound CN1C[C@@H](O)[C@H](O)[C@H]1CO UBVOJPDDTVFNFJ-HSUXUTPPSA-N 0.000 claims 1
- PXKLZLSYHLZPMK-BWZBUEFSSA-N (2r,3r,4r)-2-(hydroxymethyl)-1-propylpyrrolidine-3,4-diol Chemical compound CCCN1C[C@@H](O)[C@H](O)[C@H]1CO PXKLZLSYHLZPMK-BWZBUEFSSA-N 0.000 claims 1
- OQEBIHBLFRADNM-UOWFLXDJSA-N (2r,3r,4r)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OC[C@H]1NC[C@@H](O)[C@@H]1O OQEBIHBLFRADNM-UOWFLXDJSA-N 0.000 claims 1
- RNSKZOAZKGPNNU-FXQIFTODSA-N (2s,3s,4s)-1-(1,3-dihydroxypropan-2-yl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OCC(CO)N1C[C@H](O)[C@@H](O)[C@@H]1CO RNSKZOAZKGPNNU-FXQIFTODSA-N 0.000 claims 1
- FAACDRZBXLTQDQ-DWQAGKKUSA-N (2s,3s,4s)-1-(2,3-dihydroxypropyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OCC(O)CN1C[C@H](O)[C@@H](O)[C@@H]1CO FAACDRZBXLTQDQ-DWQAGKKUSA-N 0.000 claims 1
- UHFWEDDFLFAJHG-ACZMJKKPSA-N (2s,3s,4s)-1-(2-aminoethyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound NCCN1C[C@H](O)[C@@H](O)[C@@H]1CO UHFWEDDFLFAJHG-ACZMJKKPSA-N 0.000 claims 1
- SPYQWYTVWZBEHS-ACZMJKKPSA-N (2s,3s,4s)-1-(2-hydroxyethyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@@H]1CO SPYQWYTVWZBEHS-ACZMJKKPSA-N 0.000 claims 1
- SPPKZKQXTFBLLK-CIUDSAMLSA-N (2s,3s,4s)-1-(cyclopropylmethyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OC[C@H]1[C@H](O)[C@@H](O)CN1CC1CC1 SPPKZKQXTFBLLK-CIUDSAMLSA-N 0.000 claims 1
- SBDAWMSBMQBJRA-SRVKXCTJSA-N (2s,3s,4s)-1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OC[C@H]1[C@H](O)[C@@H](O)CN1CC1=CC=CC=C1 SBDAWMSBMQBJRA-SRVKXCTJSA-N 0.000 claims 1
- AORXTDSJOOFVRB-CIUDSAMLSA-N (2s,3s,4s)-1-butyl-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound CCCCN1C[C@H](O)[C@@H](O)[C@@H]1CO AORXTDSJOOFVRB-CIUDSAMLSA-N 0.000 claims 1
- ITBZTMURQMEUAL-ZLUOBGJFSA-N (2s,3s,4s)-2-(hydroxymethyl)-1-(2,2,2-trifluoroethyl)pyrrolidine-3,4-diol Chemical compound OC[C@H]1[C@H](O)[C@@H](O)CN1CC(F)(F)F ITBZTMURQMEUAL-ZLUOBGJFSA-N 0.000 claims 1
- UBVOJPDDTVFNFJ-ZLUOBGJFSA-N (2s,3s,4s)-2-(hydroxymethyl)-1-methylpyrrolidine-3,4-diol Chemical compound CN1C[C@H](O)[C@@H](O)[C@@H]1CO UBVOJPDDTVFNFJ-ZLUOBGJFSA-N 0.000 claims 1
- PXKLZLSYHLZPMK-FXQIFTODSA-N (2s,3s,4s)-2-(hydroxymethyl)-1-propylpyrrolidine-3,4-diol Chemical compound CCCN1C[C@H](O)[C@@H](O)[C@@H]1CO PXKLZLSYHLZPMK-FXQIFTODSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- RNSKZOAZKGPNNU-UHFFFAOYSA-N 1-(1,3-dihydroxypropan-2-yl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OCC(CO)N1CC(O)C(O)C1CO RNSKZOAZKGPNNU-UHFFFAOYSA-N 0.000 claims 1
- FAACDRZBXLTQDQ-UHFFFAOYSA-N 1-(2,3-dihydroxypropyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OCC(O)CN1CC(O)C(O)C1CO FAACDRZBXLTQDQ-UHFFFAOYSA-N 0.000 claims 1
- UHFWEDDFLFAJHG-UHFFFAOYSA-N 1-(2-aminoethyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound NCCN1CC(O)C(O)C1CO UHFWEDDFLFAJHG-UHFFFAOYSA-N 0.000 claims 1
- SPPKZKQXTFBLLK-UHFFFAOYSA-N 1-(cyclopropylmethyl)-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OCC1C(O)C(O)CN1CC1CC1 SPPKZKQXTFBLLK-UHFFFAOYSA-N 0.000 claims 1
- SBDAWMSBMQBJRA-UHFFFAOYSA-N 1-benzyl-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound OCC1C(O)C(O)CN1CC1=CC=CC=C1 SBDAWMSBMQBJRA-UHFFFAOYSA-N 0.000 claims 1
- AORXTDSJOOFVRB-UHFFFAOYSA-N 1-butyl-2-(hydroxymethyl)pyrrolidine-3,4-diol Chemical compound CCCCN1CC(O)C(O)C1CO AORXTDSJOOFVRB-UHFFFAOYSA-N 0.000 claims 1
- ITBZTMURQMEUAL-UHFFFAOYSA-N 2-(hydroxymethyl)-1-(2,2,2-trifluoroethyl)pyrrolidine-3,4-diol Chemical compound OCC1C(O)C(O)CN1CC(F)(F)F ITBZTMURQMEUAL-UHFFFAOYSA-N 0.000 claims 1
- PXKLZLSYHLZPMK-UHFFFAOYSA-N 2-(hydroxymethyl)-1-propylpyrrolidine-3,4-diol Chemical compound CCCN1CC(O)C(O)C1CO PXKLZLSYHLZPMK-UHFFFAOYSA-N 0.000 claims 1
- OQEBIHBLFRADNM-YUPRTTJUSA-N 2-hydroxymethyl-pyrrolidine-3,4-diol Chemical compound OC[C@@H]1NC[C@H](O)[C@H]1O OQEBIHBLFRADNM-YUPRTTJUSA-N 0.000 claims 1
- FQOGWNRPPJMSEC-UHFFFAOYSA-N 3-(hydroxymethyl)piperidin-4-ol Chemical compound OCC1CNCCC1O FQOGWNRPPJMSEC-UHFFFAOYSA-N 0.000 claims 1
- ITQKQYKCQXTDMI-UHFFFAOYSA-N 3-chloro-5-(hydroxymethyl)piperidin-4-ol Chemical compound OCC1CNCC(Cl)C1O ITQKQYKCQXTDMI-UHFFFAOYSA-N 0.000 claims 1
- DQKZUKLPJVJMSG-UHFFFAOYSA-N 3-fluoro-5-(hydroxymethyl)piperidin-4-ol Chemical compound OCC1CNCC(F)C1O DQKZUKLPJVJMSG-UHFFFAOYSA-N 0.000 claims 1
- DGBUIVDAWBSYNN-UHFFFAOYSA-N 4-(2-benzamidophenoxy)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC=C1 DGBUIVDAWBSYNN-UHFFFAOYSA-N 0.000 claims 1
- VVKGQPDUARVBOZ-UHFFFAOYSA-N 4-[2-[(2,3-difluorobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(F)=C1F VVKGQPDUARVBOZ-UHFFFAOYSA-N 0.000 claims 1
- APZUXEBITGMEIB-UHFFFAOYSA-N 4-[2-[(2,4-difluorobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=C(F)C=C1F APZUXEBITGMEIB-UHFFFAOYSA-N 0.000 claims 1
- VQCMQIGHKZWSLI-UHFFFAOYSA-N 4-[2-[(2,5-difluorobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC(F)=CC=C1F VQCMQIGHKZWSLI-UHFFFAOYSA-N 0.000 claims 1
- SFCOKTHIBWHMTI-UHFFFAOYSA-N 4-[2-[(2-fluorobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC=C1F SFCOKTHIBWHMTI-UHFFFAOYSA-N 0.000 claims 1
- FLLFGDHYICFTTN-UHFFFAOYSA-N 4-[2-[(3-acetylbenzoyl)amino]phenoxy]phthalic acid Chemical compound CC(=O)C1=CC=CC(C(=O)NC=2C(=CC=CC=2)OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)=C1 FLLFGDHYICFTTN-UHFFFAOYSA-N 0.000 claims 1
- ALCRXWIBODOCNW-UHFFFAOYSA-N 4-[2-[(3-aminobenzoyl)amino]phenoxy]phthalic acid Chemical compound NC1=CC=CC(C(=O)NC=2C(=CC=CC=2)OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)=C1 ALCRXWIBODOCNW-UHFFFAOYSA-N 0.000 claims 1
- AFPDZCFEHVEMNS-UHFFFAOYSA-N 4-[2-[(3-bromobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(Br)=C1 AFPDZCFEHVEMNS-UHFFFAOYSA-N 0.000 claims 1
- VCBSWJNDIGSNCL-UHFFFAOYSA-N 4-[2-[(3-chlorobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(Cl)=C1 VCBSWJNDIGSNCL-UHFFFAOYSA-N 0.000 claims 1
- QNTGQOUVJGQXDE-UHFFFAOYSA-N 4-[2-[(3-cyanobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(C#N)=C1 QNTGQOUVJGQXDE-UHFFFAOYSA-N 0.000 claims 1
- VVYJNJOVJLDUQN-UHFFFAOYSA-N 4-[2-[(3-fluorobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(F)=C1 VVYJNJOVJLDUQN-UHFFFAOYSA-N 0.000 claims 1
- ZKMKGWKWZJBKKI-UHFFFAOYSA-N 4-[2-[(3-iodobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(I)=C1 ZKMKGWKWZJBKKI-UHFFFAOYSA-N 0.000 claims 1
- VNUIPDGLBJFCJN-UHFFFAOYSA-N 4-[2-[(3-methoxybenzoyl)amino]phenoxy]phthalic acid Chemical compound COC1=CC=CC(C(=O)NC=2C(=CC=CC=2)OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)=C1 VNUIPDGLBJFCJN-UHFFFAOYSA-N 0.000 claims 1
- JVOSSUPMKPAEMQ-UHFFFAOYSA-N 4-[2-[(3-methylbenzoyl)amino]phenoxy]phthalic acid Chemical compound CC1=CC=CC(C(=O)NC=2C(=CC=CC=2)OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)=C1 JVOSSUPMKPAEMQ-UHFFFAOYSA-N 0.000 claims 1
- QTYNBBFOPMKRDO-UHFFFAOYSA-N 4-[2-[(3-nitrobenzoyl)amino]-4-(trifluoromethyl)phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(F)(F)F)C=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 QTYNBBFOPMKRDO-UHFFFAOYSA-N 0.000 claims 1
- XLLFYCMEMKJYQC-UHFFFAOYSA-N 4-[2-[(3-nitrobenzoyl)amino]phenyl]sulfanylphthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1SC1=CC=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 XLLFYCMEMKJYQC-UHFFFAOYSA-N 0.000 claims 1
- MUKOHJFPFAAHLV-UHFFFAOYSA-N 4-[2-[(3-nitrophenyl)methylamino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NCC1=CC=CC([N+]([O-])=O)=C1 MUKOHJFPFAAHLV-UHFFFAOYSA-N 0.000 claims 1
- HRNDZVZGISDBSH-UHFFFAOYSA-N 4-[2-[(4-fluorobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=C(F)C=C1 HRNDZVZGISDBSH-UHFFFAOYSA-N 0.000 claims 1
- KNIRYHSJMHOIJZ-UHFFFAOYSA-N 4-[2-[[2-fluoro-5-(trifluoromethyl)benzoyl]amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC(C(F)(F)F)=CC=C1F KNIRYHSJMHOIJZ-UHFFFAOYSA-N 0.000 claims 1
- PVEZUVRSEDFBED-UHFFFAOYSA-N 4-[2-[[3-(dimethylamino)benzoyl]amino]phenoxy]phthalic acid Chemical compound CN(C)C1=CC=CC(C(=O)NC=2C(=CC=CC=2)OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)=C1 PVEZUVRSEDFBED-UHFFFAOYSA-N 0.000 claims 1
- BLFABBPOEGGGBW-UHFFFAOYSA-N 4-[2-[[3-(trifluoromethoxy)benzoyl]amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(OC(F)(F)F)=C1 BLFABBPOEGGGBW-UHFFFAOYSA-N 0.000 claims 1
- AFJVJGBEGXWQNS-UHFFFAOYSA-N 4-[2-[[3-(trifluoromethyl)benzoyl]amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 AFJVJGBEGXWQNS-UHFFFAOYSA-N 0.000 claims 1
- MKQSGNJOMQDZCH-UHFFFAOYSA-N 4-[4-[(3-nitrobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 MKQSGNJOMQDZCH-UHFFFAOYSA-N 0.000 claims 1
- BWWJUWJMTJBQPN-UHFFFAOYSA-N 4-[4-[(4-iodobenzoyl)amino]-2-[(3-nitrobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC(C(=C1)NC(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=CC=C1NC(=O)C1=CC=C(I)C=C1 BWWJUWJMTJBQPN-UHFFFAOYSA-N 0.000 claims 1
- UREVCBHMCDVYLI-UHFFFAOYSA-N 4-[4-acetamido-2-[(3-nitrobenzoyl)amino]phenoxy]phthalic acid Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C(=O)NC1=CC(NC(=O)C)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 UREVCBHMCDVYLI-UHFFFAOYSA-N 0.000 claims 1
- GJXZFZQTSAOZSF-UHFFFAOYSA-N 4-[4-amino-2-[(3-nitrobenzoyl)amino]phenoxy]phthalic acid Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C(=O)NC1=CC(N)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 GJXZFZQTSAOZSF-UHFFFAOYSA-N 0.000 claims 1
- UITDURQSKACGOI-UHFFFAOYSA-N 4-[4-benzamido-2-[(3-nitrobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC(C(=C1)NC(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=CC=C1NC(=O)C1=CC=CC=C1 UITDURQSKACGOI-UHFFFAOYSA-N 0.000 claims 1
- OAZBMVAPRVXFSM-UHFFFAOYSA-N 4-[4-bromo-2-[(3-nitrobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(Br)C=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 OAZBMVAPRVXFSM-UHFFFAOYSA-N 0.000 claims 1
- JNEHUYVPZOKWNK-UHFFFAOYSA-N 4-[4-cyano-2-[(3-nitrobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C#N)C=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 JNEHUYVPZOKWNK-UHFFFAOYSA-N 0.000 claims 1
- SXQSXGKQUDBDKG-UHFFFAOYSA-N 4-[4-fluoro-2-[(3-nitrobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(F)C=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 SXQSXGKQUDBDKG-UHFFFAOYSA-N 0.000 claims 1
- VIXZBRNAXCGCCC-UHFFFAOYSA-N 4-[4-methoxycarbonyl-2-[(3-nitrobenzoyl)amino]phenoxy]phthalic acid Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C(=O)NC1=CC(C(=O)OC)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 VIXZBRNAXCGCCC-UHFFFAOYSA-N 0.000 claims 1
- JSWGGLZASDOWGM-UHFFFAOYSA-N 4-[4-methyl-2-[(3-nitrobenzoyl)amino]phenoxy]phthalic acid Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C(=O)NC1=CC(C)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 JSWGGLZASDOWGM-UHFFFAOYSA-N 0.000 claims 1
- IVZCUPXQGWYXRH-UHFFFAOYSA-N 4-[5-fluoro-2-[(3-nitrobenzoyl)amino]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC(F)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 IVZCUPXQGWYXRH-UHFFFAOYSA-N 0.000 claims 1
- AJYMAGBHSPVRBG-UHFFFAOYSA-N 4-[5-methyl-2-[(3-nitrobenzoyl)amino]phenoxy]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1OC1=CC(C)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 AJYMAGBHSPVRBG-UHFFFAOYSA-N 0.000 claims 1
- MCMVVHHPHOTFDO-UHFFFAOYSA-N 4-chloro-5-(hydroxymethyl)piperidin-3-ol Chemical compound OCC1CNCC(O)C1Cl MCMVVHHPHOTFDO-UHFFFAOYSA-N 0.000 claims 1
- AMRGLJFRLTZTMG-UHFFFAOYSA-N 4-fluoro-5-(hydroxymethyl)piperidin-3-ol Chemical compound OCC1CNCC(O)C1F AMRGLJFRLTZTMG-UHFFFAOYSA-N 0.000 claims 1
- VFYAZSTYKPFSFL-UHFFFAOYSA-N 4-{2,4-bis[(3-nitrobenzoyl)amino]phenoxy}phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC(C(=C1)NC(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 VFYAZSTYKPFSFL-UHFFFAOYSA-N 0.000 claims 1
- NAQUAVBNIYTIIS-UHFFFAOYSA-N 4-{2-[(3-nitrobenzoyl)amino]phenoxy}phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 NAQUAVBNIYTIIS-UHFFFAOYSA-N 0.000 claims 1
- MMWSFXGSQAOMQI-UHFFFAOYSA-N 5-(2-hydroxyethyl)piperidine-3,4-diol Chemical compound OCCC1CNCC(O)C1O MMWSFXGSQAOMQI-UHFFFAOYSA-N 0.000 claims 1
- KTXBXDGOZMHNIC-UHFFFAOYSA-N 5-(chloromethyl)piperidine-3,4-diol Chemical compound OC1CNCC(CCl)C1O KTXBXDGOZMHNIC-UHFFFAOYSA-N 0.000 claims 1
- BEQPGACEJJJLEA-UHFFFAOYSA-N 5-(fluoromethyl)piperidine-3,4-diol Chemical compound OC1CNCC(CF)C1O BEQPGACEJJJLEA-UHFFFAOYSA-N 0.000 claims 1
- WIWXVOPKTGFUMA-UHFFFAOYSA-M 5-(hydroxymethyl)-1,1-dimethylpiperidin-1-ium-3,4-diol;chloride Chemical compound [Cl-].C[N+]1(C)CC(O)C(O)C(CO)C1 WIWXVOPKTGFUMA-UHFFFAOYSA-M 0.000 claims 1
- CYCTZRRPYHKVQQ-UHFFFAOYSA-N 5-(hydroxymethyl)-1-methylpiperidine-3,4-diol Chemical compound CN1CC(O)C(O)C(CO)C1 CYCTZRRPYHKVQQ-UHFFFAOYSA-N 0.000 claims 1
- XCPUOKRBVCHXNS-UHFFFAOYSA-N 5-(hydroxymethyl)piperidin-3-ol Chemical compound OCC1CNCC(O)C1 XCPUOKRBVCHXNS-UHFFFAOYSA-N 0.000 claims 1
- UIALTIIMHGHQRO-UHFFFAOYSA-N 5-ethylpiperidine-3,4-diol Chemical compound CCC1CNCC(O)C1O UIALTIIMHGHQRO-UHFFFAOYSA-N 0.000 claims 1
- SOWLFRYBIBVUNW-UHFFFAOYSA-N 5-phenylpiperidine-3,4-diol Chemical compound OC1C(O)CNCC1C1=CC=CC=C1 SOWLFRYBIBVUNW-UHFFFAOYSA-N 0.000 claims 1
- XVRLSSYAFOIBQU-UHFFFAOYSA-N 5-propan-2-ylpiperidine-3,4-diol Chemical compound CC(C)C1CNCC(O)C1O XVRLSSYAFOIBQU-UHFFFAOYSA-N 0.000 claims 1
- KDHNIDSJJULIGE-UHFFFAOYSA-N 5-propylpiperidine-3,4-diol Chemical compound CCCC1CNCC(O)C1O KDHNIDSJJULIGE-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- ICJDWETZEPFXIX-KEWYIRBNSA-N CC[C@H]1OC(OC)[C@H](O)[C@@H](O)[C@@H]1O Chemical compound CC[C@H]1OC(OC)[C@H](O)[C@@H](O)[C@@H]1O ICJDWETZEPFXIX-KEWYIRBNSA-N 0.000 claims 1
- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 claims 1
- 239000000674 adrenergic antagonist Substances 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- FCXGEEJWNLHSQW-UHFFFAOYSA-N dimethyl 4-(2-benzamidophenoxy)benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC=C1 FCXGEEJWNLHSQW-UHFFFAOYSA-N 0.000 claims 1
- FZDIOJAQYNNMDD-UHFFFAOYSA-N dimethyl 4-[2,4-bis[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC(C(=C1)NC(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 FZDIOJAQYNNMDD-UHFFFAOYSA-N 0.000 claims 1
- MUAOHNWPBPJTCX-UHFFFAOYSA-N dimethyl 4-[2-[(2,3-difluorobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(F)=C1F MUAOHNWPBPJTCX-UHFFFAOYSA-N 0.000 claims 1
- ZFDCKWGKMGHAHU-UHFFFAOYSA-N dimethyl 4-[2-[(2,4-difluorobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=C(F)C=C1F ZFDCKWGKMGHAHU-UHFFFAOYSA-N 0.000 claims 1
- OVOVTEJWEVOJQA-UHFFFAOYSA-N dimethyl 4-[2-[(2,5-difluorobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC(F)=CC=C1F OVOVTEJWEVOJQA-UHFFFAOYSA-N 0.000 claims 1
- FOEMSVVLOJVPQA-UHFFFAOYSA-N dimethyl 4-[2-[(2-fluorobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC=C1F FOEMSVVLOJVPQA-UHFFFAOYSA-N 0.000 claims 1
- OVDUANNCKBGWQN-UHFFFAOYSA-N dimethyl 4-[2-[(3-acetylbenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(C(C)=O)=C1 OVDUANNCKBGWQN-UHFFFAOYSA-N 0.000 claims 1
- OTGHWRBMKUJNAF-UHFFFAOYSA-N dimethyl 4-[2-[(3-aminobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(N)=C1 OTGHWRBMKUJNAF-UHFFFAOYSA-N 0.000 claims 1
- NFPQLJCRDAFOPP-UHFFFAOYSA-N dimethyl 4-[2-[(3-bromobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(Br)=C1 NFPQLJCRDAFOPP-UHFFFAOYSA-N 0.000 claims 1
- XHUSLRFPEVSIEL-UHFFFAOYSA-N dimethyl 4-[2-[(3-chlorobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(Cl)=C1 XHUSLRFPEVSIEL-UHFFFAOYSA-N 0.000 claims 1
- LUTZRRDKNFEVNC-UHFFFAOYSA-N dimethyl 4-[2-[(3-cyanobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(C#N)=C1 LUTZRRDKNFEVNC-UHFFFAOYSA-N 0.000 claims 1
- OAGAGQMSBFGEFP-UHFFFAOYSA-N dimethyl 4-[2-[(3-fluorobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(F)=C1 OAGAGQMSBFGEFP-UHFFFAOYSA-N 0.000 claims 1
- HGPRLIXTWNNYIJ-UHFFFAOYSA-N dimethyl 4-[2-[(3-iodobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(I)=C1 HGPRLIXTWNNYIJ-UHFFFAOYSA-N 0.000 claims 1
- VDJVSUZCSFQEGQ-UHFFFAOYSA-N dimethyl 4-[2-[(3-methoxybenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(OC)=C1 VDJVSUZCSFQEGQ-UHFFFAOYSA-N 0.000 claims 1
- FAAVFFSKXPNVLV-UHFFFAOYSA-N dimethyl 4-[2-[(3-methylbenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(C)=C1 FAAVFFSKXPNVLV-UHFFFAOYSA-N 0.000 claims 1
- LAHFMWBSDGASDT-UHFFFAOYSA-N dimethyl 4-[2-[(3-nitrobenzoyl)amino]-4-(trifluoromethyl)phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=C(C(F)(F)F)C=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 LAHFMWBSDGASDT-UHFFFAOYSA-N 0.000 claims 1
- DLQVQMNIWMDHGG-UHFFFAOYSA-N dimethyl 4-[2-[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 DLQVQMNIWMDHGG-UHFFFAOYSA-N 0.000 claims 1
- HREOUTRZTDTJJP-UHFFFAOYSA-N dimethyl 4-[2-[(3-nitrobenzoyl)amino]phenyl]sulfanylbenzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1SC1=CC=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 HREOUTRZTDTJJP-UHFFFAOYSA-N 0.000 claims 1
- KEFVWPZJUVQJGV-UHFFFAOYSA-N dimethyl 4-[2-[(3-nitrophenyl)methylamino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NCC1=CC=CC([N+]([O-])=O)=C1 KEFVWPZJUVQJGV-UHFFFAOYSA-N 0.000 claims 1
- HECYLQJHWLPCDV-UHFFFAOYSA-N dimethyl 4-[2-[(4-fluorobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=C(F)C=C1 HECYLQJHWLPCDV-UHFFFAOYSA-N 0.000 claims 1
- VZGXLJPNZBFBHI-UHFFFAOYSA-N dimethyl 4-[2-[[2-fluoro-5-(trifluoromethyl)benzoyl]amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC(C(F)(F)F)=CC=C1F VZGXLJPNZBFBHI-UHFFFAOYSA-N 0.000 claims 1
- VGYNLWKLCXBTRB-UHFFFAOYSA-N dimethyl 4-[2-[[3-(dimethylamino)benzoyl]amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(N(C)C)=C1 VGYNLWKLCXBTRB-UHFFFAOYSA-N 0.000 claims 1
- QXNJPFNSYHOOAG-UHFFFAOYSA-N dimethyl 4-[2-[[3-(trifluoromethoxy)benzoyl]amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(OC(F)(F)F)=C1 QXNJPFNSYHOOAG-UHFFFAOYSA-N 0.000 claims 1
- MKADAAWCNLMZLG-UHFFFAOYSA-N dimethyl 4-[2-[[3-(trifluoromethyl)benzoyl]amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 MKADAAWCNLMZLG-UHFFFAOYSA-N 0.000 claims 1
- IAKJTGDECMFKEH-UHFFFAOYSA-N dimethyl 4-[4-[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 IAKJTGDECMFKEH-UHFFFAOYSA-N 0.000 claims 1
- CZSORXIJJWKPQI-UHFFFAOYSA-N dimethyl 4-[4-[(4-iodobenzoyl)amino]-2-[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC(C(=C1)NC(=O)C=2C=C(C=CC=2)[N+]([O-])=O)=CC=C1NC(=O)C1=CC=C(I)C=C1 CZSORXIJJWKPQI-UHFFFAOYSA-N 0.000 claims 1
- OIJGUEADSJUHBK-UHFFFAOYSA-N dimethyl 4-[4-acetamido-2-[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=C(NC(C)=O)C=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 OIJGUEADSJUHBK-UHFFFAOYSA-N 0.000 claims 1
- GGUCVQBQCNBCRS-UHFFFAOYSA-N dimethyl 4-[4-amino-2-[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=C(N)C=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 GGUCVQBQCNBCRS-UHFFFAOYSA-N 0.000 claims 1
- AVVMNJOGOKZHEH-UHFFFAOYSA-N dimethyl 4-[4-bromo-2-[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=C(Br)C=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 AVVMNJOGOKZHEH-UHFFFAOYSA-N 0.000 claims 1
- OHLYWEPWAJOTLG-UHFFFAOYSA-N dimethyl 4-[4-cyano-2-[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=C(C#N)C=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 OHLYWEPWAJOTLG-UHFFFAOYSA-N 0.000 claims 1
- DVJNBBPZGGEJSL-UHFFFAOYSA-N dimethyl 4-[4-fluoro-2-[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=C(F)C=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 DVJNBBPZGGEJSL-UHFFFAOYSA-N 0.000 claims 1
- FQZNZYWDGGARJQ-UHFFFAOYSA-N dimethyl 4-[4-methoxycarbonyl-2-[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C(=O)NC1=CC(C(=O)OC)=CC=C1OC1=CC=C(C(=O)OC)C(C(=O)OC)=C1 FQZNZYWDGGARJQ-UHFFFAOYSA-N 0.000 claims 1
- SAEILBIRVJGPMV-UHFFFAOYSA-N dimethyl 4-[4-methyl-2-[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC=C(C)C=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 SAEILBIRVJGPMV-UHFFFAOYSA-N 0.000 claims 1
- SRSWXBBLIUZNMY-UHFFFAOYSA-N dimethyl 4-[5-fluoro-2-[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC(F)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 SRSWXBBLIUZNMY-UHFFFAOYSA-N 0.000 claims 1
- XOTWJIRZYGLPLG-UHFFFAOYSA-N dimethyl 4-[5-methyl-2-[(3-nitrobenzoyl)amino]phenoxy]benzene-1,2-dicarboxylate Chemical compound C1=C(C(=O)OC)C(C(=O)OC)=CC=C1OC1=CC(C)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1 XOTWJIRZYGLPLG-UHFFFAOYSA-N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- IVHLSEUCKYUWLB-UHFFFAOYSA-N n-[2-(1,3-dioxoisoindol-5-yl)oxyphenyl]-3-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NC=2C(=CC=CC=2)OC=2C=C3C(=O)NC(=O)C3=CC=2)=C1 IVHLSEUCKYUWLB-UHFFFAOYSA-N 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 CC1C(*)N(*)C(*)C1* Chemical compound CC1C(*)N(*)C(*)C1* 0.000 description 2
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200201630 | 2002-10-28 | ||
| US10/429,625 US20040082641A1 (en) | 2002-10-28 | 2003-05-05 | Use of glycogen phosphorylase inhibitors for treatment of cardiovascular diseases |
| US10/429,626 US6960610B2 (en) | 2002-10-28 | 2003-05-05 | Use of glycogen phosphorylase inhibitors for treatment of cardiovascular diseases |
| PCT/DK2003/000695 WO2004037233A2 (en) | 2002-10-28 | 2003-10-14 | Use of glycogen phosphorylase inhibitors for treatment of cardiovascular diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006507359A JP2006507359A (ja) | 2006-03-02 |
| JP2006507359A5 true JP2006507359A5 (enExample) | 2006-11-30 |
Family
ID=32180137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005501508A Withdrawn JP2006507359A (ja) | 2002-10-28 | 2003-10-14 | 心循環器疾患の治療のためのグリコーゲンホスホリラーゼ阻害剤の使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20050054618A1 (enExample) |
| EP (1) | EP1558245A2 (enExample) |
| JP (1) | JP2006507359A (enExample) |
| AU (1) | AU2003273762A1 (enExample) |
| WO (1) | WO2004037233A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20110235A1 (es) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | Combinaciones farmaceuticas que comprenden linagliptina y metmorfina |
| CA2758271C (en) | 2009-04-09 | 2018-06-05 | Robert Boyd | Methods for preventing and/or treating lysosomal storage disorders |
| JP5634498B2 (ja) * | 2009-04-09 | 2014-12-03 | アミカス セラピューティックス インコーポレイテッド | 中枢神経系の変性障害の予防および／または治療方法 |
| KR101880411B1 (ko) | 2009-10-19 | 2018-07-19 | 아미쿠스 세라퓨틱스, 인코포레이티드 | 중추신경계의 퇴행성 질환을 예방 및/또는 치료하는 신규 조성물 |
| CN102647905B (zh) | 2009-10-19 | 2015-09-09 | 阿米库斯治疗学公司 | 用于预防和/或治疗溶酶体贮积失调的新颖组合物 |
| JP5830534B2 (ja) | 2010-07-09 | 2015-12-09 | ファイザー・リミテッドＰｆｉｚｅｒ Ｌｉｍｉｔｅｄ | 化合物 |
| JP5860045B2 (ja) | 2010-07-09 | 2016-02-16 | ファイザー・リミテッドＰｆｉｚｅｒ Ｌｉｍｉｔｅｄ | 化合物 |
| WO2020023390A1 (en) | 2018-07-25 | 2020-01-30 | Modernatx, Inc. | Mrna based enzyme replacement therapy combined with a pharmacological chaperone for the treatment of lysosomal storage disorders |
| WO2020243415A2 (en) | 2019-05-31 | 2020-12-03 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| MX2021014441A (es) | 2019-05-31 | 2022-01-06 | Ikena Oncology Inc | Inhibidores del dominio asociado mejorador de la transcripcion (tead) y usos de los mismos. |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5338829A (en) * | 1988-04-20 | 1994-08-16 | Trustees Of The University Of Pennsylvania | Peptides derived from human immunodeficiency virus-1 GP160 |
| US5242687A (en) * | 1989-03-15 | 1993-09-07 | Tkb Associates Limited Partnership | Method of reducing cellular immune response involving T-cells using CD8-bearing antigen presenting cells |
| US5759551A (en) * | 1993-04-27 | 1998-06-02 | United Biomedical, Inc. | Immunogenic LHRH peptide constructs and synthetic universal immune stimulators for vaccines |
| US5705388A (en) * | 1994-12-23 | 1998-01-06 | Ribozyme Pharmaceuticals, Inc. | CETP Ribozymes |
| AU724003B2 (en) * | 1995-09-08 | 2000-09-07 | Novo Nordisk A/S | 2-alkylpyrrolidines |
| US5998463A (en) * | 1998-02-27 | 1999-12-07 | Pfizer Inc | Glycogen phosphorylase inhibitors |
| AU2535700A (en) * | 1999-02-12 | 2000-08-29 | Novo Nordisk A/S | Use of pyrrolidine derivatives for the manufacture of a pharmaceutical composition for the treatment or prophylaxis of obesity or appetite regulation |
-
2003
- 2003-10-14 EP EP03757718A patent/EP1558245A2/en not_active Withdrawn
- 2003-10-14 AU AU2003273762A patent/AU2003273762A1/en not_active Abandoned
- 2003-10-14 WO PCT/DK2003/000695 patent/WO2004037233A2/en not_active Ceased
- 2003-10-14 JP JP2005501508A patent/JP2006507359A/ja not_active Withdrawn
-
2004
- 2004-09-17 US US10/943,548 patent/US20050054618A1/en not_active Abandoned
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