IL96875A - History of Oreido of poly-4-amino-2-carboxy-1-methyl-pyrroles - Google Patents
History of Oreido of poly-4-amino-2-carboxy-1-methyl-pyrrolesInfo
- Publication number
- IL96875A IL96875A IL9687591A IL9687591A IL96875A IL 96875 A IL96875 A IL 96875A IL 9687591 A IL9687591 A IL 9687591A IL 9687591 A IL9687591 A IL 9687591A IL 96875 A IL96875 A IL 96875A
- Authority
- IL
- Israel
- Prior art keywords
- imino
- bis
- methyl
- pyrrole
- pyrrolecarbonyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 79
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 title abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 56
- 239000002253 acid Substances 0.000 claims abstract description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000005864 Sulphur Substances 0.000 claims abstract description 6
- 239000004037 angiogenesis inhibitor Substances 0.000 claims abstract description 5
- 229940121369 angiogenesis inhibitor Drugs 0.000 claims abstract description 5
- 235000000346 sugar Nutrition 0.000 claims abstract description 5
- 125000002541 furyl group Chemical group 0.000 claims abstract description 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims abstract description 4
- -1 N-methyl-4-aminopyrrol-2-yl Chemical group 0.000 claims description 99
- 238000000034 method Methods 0.000 claims description 23
- 230000002378 acidificating effect Effects 0.000 claims description 15
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 10
- HEWDOWUUTBCVJP-UHFFFAOYSA-N naphthalene-1,6-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 HEWDOWUUTBCVJP-UHFFFAOYSA-N 0.000 claims description 8
- INMHJULHWVWVFN-UHFFFAOYSA-N naphthalene-1,3,5-trisulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC(S(O)(=O)=O)=C21 INMHJULHWVWVFN-UHFFFAOYSA-N 0.000 claims description 6
- FKORGLNGEASTQE-UHFFFAOYSA-N naphthalene-1,3-disulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC(S(O)(=O)=O)=C21 FKORGLNGEASTQE-UHFFFAOYSA-N 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 230000001627 detrimental effect Effects 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- ZPBSAMLXSQCSOX-UHFFFAOYSA-N naphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 ZPBSAMLXSQCSOX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 claims description 3
- MBPFNOMGYSRGQZ-PBXRRBTRSA-N 2-deoxy-D-glucose 6-phosphate Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@H](O)CC=O MBPFNOMGYSRGQZ-PBXRRBTRSA-N 0.000 claims description 3
- SNBMSOSVQGSNTI-PBXRRBTRSA-N OS(=O)(=O)OC[C@@H](O)[C@@H](O)[C@H](O)CC=O Chemical compound OS(=O)(=O)OC[C@@H](O)[C@@H](O)[C@H](O)CC=O SNBMSOSVQGSNTI-PBXRRBTRSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- FEWNRIKJXAQRJJ-UHFFFAOYSA-N naphthalene-1,3,7-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC=C21 FEWNRIKJXAQRJJ-UHFFFAOYSA-N 0.000 claims description 3
- HYFMZOAPNQAXHU-UHFFFAOYSA-N naphthalene-1,7-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC=C21 HYFMZOAPNQAXHU-UHFFFAOYSA-N 0.000 claims description 3
- FITZJYAVATZPMJ-UHFFFAOYSA-N naphthalene-2,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(S(=O)(=O)O)=CC=C21 FITZJYAVATZPMJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 108700012920 TNF Proteins 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- FMHFHTQXVYDQRT-UHFFFAOYSA-N naphthalene-1,4,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC=C21 FMHFHTQXVYDQRT-UHFFFAOYSA-N 0.000 claims description 2
- VILFVXYKHXVYAB-UHFFFAOYSA-N naphthalene-2,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VILFVXYKHXVYAB-UHFFFAOYSA-N 0.000 claims description 2
- 230000000069 prophylactic effect Effects 0.000 claims description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 150000003233 pyrroles Chemical class 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000002837 carbocyclic group Chemical group 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- XZNVRCJXZWONQE-UHFFFAOYSA-K trisodium;naphthalene-1,3,5-trisulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(S(=O)(=O)[O-])=CC(S([O-])(=O)=O)=C21 XZNVRCJXZWONQE-UHFFFAOYSA-K 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 208000037976 chronic inflammation Diseases 0.000 description 2
- 230000006020 chronic inflammation Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000010255 intramuscular injection Methods 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- UPBAOYRENQEPJO-UHFFFAOYSA-N n-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide Chemical compound CN1C=C(NC=O)C=C1C(=O)NC1=CN(C)C(C(=O)NC2=CN(C)C(C(=O)NCCC(N)=N)=C2)=C1 UPBAOYRENQEPJO-UHFFFAOYSA-N 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- BBCBMZZXCBYNRL-UHFFFAOYSA-N naphthalene-1,6,7-trisulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC2=C1 BBCBMZZXCBYNRL-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- OOHAMBODAKJXMR-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;n,n-diethylethanamine Chemical compound CCN(CC)CC.OCCN(CCO)CCO OOHAMBODAKJXMR-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 108010006654 Bleomycin Proteins 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 206010063094 Cerebral malaria Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- 208000009329 Graft vs Host Disease Diseases 0.000 description 1
- 101000837626 Homo sapiens Thyroid hormone receptor alpha Proteins 0.000 description 1
- 108060003951 Immunoglobulin Proteins 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- SGDBTWWWUNNDEQ-UHFFFAOYSA-N Merphalan Chemical compound OC(=O)C(N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 229930192392 Mitomycin Natural products 0.000 description 1
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 102100028702 Thyroid hormone receptor alpha Human genes 0.000 description 1
- QENRLWZEQDOEOC-UHFFFAOYSA-L [Na+].[Na+].N1=CC=CC2=CC(=CC=C12)S(=O)(=O)[O-].N1=CC=CC2=CC(=CC=C12)S(=O)(=O)[O-] Chemical compound [Na+].[Na+].N1=CC=CC2=CC(=CC=C12)S(=O)(=O)[O-].N1=CC=CC2=CC(=CC=C12)S(=O)(=O)[O-] QENRLWZEQDOEOC-UHFFFAOYSA-L 0.000 description 1
- NRWWXYQCNZUYML-UHFFFAOYSA-J [Na+].[Na+].[Na+].[Na+].C1=C(C=CC2=CC(=CC=C12)S(=O)(=O)[O-])S(=O)(=O)[O-].C1=C(C=CC2=CC(=CC=C12)S(=O)(=O)[O-])S(=O)(=O)[O-] Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(C=CC2=CC(=CC=C12)S(=O)(=O)[O-])S(=O)(=O)[O-].C1=C(C=CC2=CC(=CC=C12)S(=O)(=O)[O-])S(=O)(=O)[O-] NRWWXYQCNZUYML-UHFFFAOYSA-J 0.000 description 1
- UQLPMUATSFTEFH-UHFFFAOYSA-H [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].C1=C(C=C(C2=CC(=CC=C12)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-].C1=C(C=C(C2=CC(=CC=C12)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-] Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].C1=C(C=C(C2=CC(=CC=C12)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-].C1=C(C=C(C2=CC(=CC=C12)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)[O-] UQLPMUATSFTEFH-UHFFFAOYSA-H 0.000 description 1
- JFGAVIUAYHTCFS-UHFFFAOYSA-N [Na].[Na].Cl Chemical compound [Na].[Na].Cl JFGAVIUAYHTCFS-UHFFFAOYSA-N 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960001561 bleomycin Drugs 0.000 description 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 210000003711 chorioallantoic membrane Anatomy 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- AWEISNYJGLMMOH-UHFFFAOYSA-L dipotassium naphthalene-1,3-disulfonate Chemical compound [K+].[K+].C1(=CC(=CC2=CC=CC=C12)S(=O)(=O)[O-])S(=O)(=O)[O-] AWEISNYJGLMMOH-UHFFFAOYSA-L 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
- 229960005420 etoposide Drugs 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 108010074605 gamma-Globulins Proteins 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 102000057041 human TNF Human genes 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 102000018358 immunoglobulin Human genes 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229960004393 lidocaine hydrochloride Drugs 0.000 description 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960004857 mitomycin Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012514 monoclonal antibody product Substances 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- YKFJUBNDHOLBNN-UHFFFAOYSA-N naphthalene-2,3-disulfonic acid Chemical compound C1=CC=C2C=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC2=C1 YKFJUBNDHOLBNN-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- PYTIEQGZGAAZDC-UHFFFAOYSA-N quinoline-5,7-disulfonic acid Chemical compound C1=CC=NC2=CC(S(=O)(=O)O)=CC(S(O)(=O)=O)=C21 PYTIEQGZGAAZDC-UHFFFAOYSA-N 0.000 description 1
- SXVRECLPTCOMIA-UHFFFAOYSA-N quinoline-8-sulfonic acid Chemical compound C1=CN=C2C(S(=O)(=O)O)=CC=CC2=C1 SXVRECLPTCOMIA-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 108010042747 stallimycin Proteins 0.000 description 1
- 229950009902 stallimycin Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- HYSBOMDYYIJYKS-UHFFFAOYSA-J tetrasodium naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)c1ccc2ccc(cc2c1)S([O-])(=O)=O.[O-]S(=O)(=O)c1ccc2ccc(cc2c1)S([O-])(=O)=O HYSBOMDYYIJYKS-UHFFFAOYSA-J 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-CFWMRBGOSA-N 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polyamides (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909000644A GB9000644D0 (en) | 1990-01-11 | 1990-01-11 | New ureido derivatives of poly-4-amino-2-carboxy-1-methyl compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL96875A0 IL96875A0 (en) | 1992-03-29 |
| IL96875A true IL96875A (en) | 1995-03-30 |
Family
ID=10669147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9687591A IL96875A (en) | 1990-01-11 | 1991-01-03 | History of Oreido of poly-4-amino-2-carboxy-1-methyl-pyrroles |
Country Status (33)
| Country | Link |
|---|---|
| US (3) | US5260329A (no) |
| EP (1) | EP0462258B1 (no) |
| JP (1) | JP3121343B2 (no) |
| KR (1) | KR0176258B1 (no) |
| CN (1) | CN1032750C (no) |
| AT (1) | ATE131810T1 (no) |
| AU (1) | AU647446B2 (no) |
| BG (1) | BG60534B2 (no) |
| CA (1) | CA2050331C (no) |
| CZ (1) | CZ285251B6 (no) |
| DE (1) | DE69115570T2 (no) |
| DK (1) | DK0462258T3 (no) |
| ES (1) | ES2084153T3 (no) |
| FI (1) | FI99011C (no) |
| GB (1) | GB9000644D0 (no) |
| GR (1) | GR3018767T3 (no) |
| HK (1) | HK1006455A1 (no) |
| HR (1) | HRP930311B1 (no) |
| HU (2) | HUT61280A (no) |
| IE (1) | IE69462B1 (no) |
| IL (1) | IL96875A (no) |
| MX (1) | MX9203119A (no) |
| MY (1) | MY107890A (no) |
| NO (1) | NO176274C (no) |
| NZ (1) | NZ236707A (no) |
| PT (1) | PT96455B (no) |
| RU (1) | RU2078079C1 (no) |
| SI (1) | SI9110025B (no) |
| SK (1) | SK280190B6 (no) |
| UA (1) | UA32513A (no) |
| WO (1) | WO1991010649A1 (no) |
| YU (1) | YU48548B (no) |
| ZA (1) | ZA91177B (no) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9000644D0 (en) * | 1990-01-11 | 1990-03-14 | Erba Carlo Spa | New ureido derivatives of poly-4-amino-2-carboxy-1-methyl compounds |
| WO1992013838A1 (en) * | 1991-02-06 | 1992-08-20 | Synphar Laboratories, Inc. | Oligopeptide antiretroviral agents |
| GB2261661A (en) * | 1991-11-21 | 1993-05-26 | Erba Carlo Spa | Derivatives of poly-4-amino-2-carboxy-1-methyl pyrroles |
| GB9216962D0 (en) * | 1992-08-11 | 1992-09-23 | Erba Carlo Spa | Therapeutically active naphthalenesulfonic-pyrrolecarboxamido derivatives |
| GB9225475D0 (en) * | 1992-12-05 | 1993-01-27 | Imp Cancer Res Tech | Compounds to combat angiogenesis |
| US6114355A (en) * | 1993-03-01 | 2000-09-05 | D'amato; Robert | Methods and compositions for inhibition of angiogenesis |
| US5629327A (en) * | 1993-03-01 | 1997-05-13 | Childrens Hospital Medical Center Corp. | Methods and compositions for inhibition of angiogenesis |
| US8143283B1 (en) | 1993-03-01 | 2012-03-27 | The Children's Medical Center Corporation | Methods for treating blood-born tumors with thalidomide |
| GB9304589D0 (en) * | 1993-03-05 | 1993-04-21 | Erba Carlo Spa | Biologically active ureido derivatives useful as antimetastic agents |
| GB9307948D0 (en) * | 1993-04-16 | 1993-06-02 | Erba Carlo Spa | Biologically active ureido derivatives useful in the treatment of lentivirus-induced disease |
| DE4320157A1 (de) * | 1993-06-18 | 1994-12-22 | Bayer Ag | Verwendung von 1,2,4-Dithiazolium-Salzen als Chemotherapeutica |
| US5463063A (en) * | 1993-07-02 | 1995-10-31 | Celgene Corporation | Ring closure of N-phthaloylglutamines |
| GB9403909D0 (en) * | 1994-03-01 | 1994-04-20 | Erba Carlo Spa | Ureido derivatives of naphthalenephosphonic acids and process for their preparation |
| GB9504065D0 (en) * | 1995-03-01 | 1995-04-19 | Pharmacia Spa | Poly-pyrrolecarboxamidonaphthalenic acid derivatives |
| US6346510B1 (en) | 1995-10-23 | 2002-02-12 | The Children's Medical Center Corporation | Therapeutic antiangiogenic endostatin compositions |
| GB2310207A (en) * | 1996-02-15 | 1997-08-20 | Pharmacia Spa | Antiviral ureido derivatives of substituted heterocyclic compounds |
| ATE493983T1 (de) * | 1996-11-05 | 2011-01-15 | Childrens Medical Center | Thalidomide und dexamethason für die behandlung von tumors |
| GB9713732D0 (en) * | 1997-06-27 | 1997-09-03 | Pharmacia & Upjohn Spa | Substituted triazinic compounds |
| GB9713733D0 (en) * | 1997-06-27 | 1997-09-03 | Pharmacia & Upjohn Spa | Poly-branched polycarboxamido compounds |
| US6562859B1 (en) | 1997-12-04 | 2003-05-13 | The United States Of America As Represented By The Department Of Health And Human Services | Ureido derivatives of poly-4-amino-2-carboxy-1-methyl pyrrole compounds for inhibition of inflammation |
| DE69831013T2 (de) * | 1997-12-22 | 2006-04-20 | Bayer Pharmaceuticals Corp., West Haven | Inhibierung der raf-kinase durch substituierte heterocyclische harnstoffverbindungen |
| GB9727524D0 (en) | 1997-12-31 | 1998-02-25 | Pharmacia & Upjohn Spa | Synergistic antitumor composition containing a biologically active ureido compound |
| US7378400B2 (en) * | 1999-02-01 | 2008-05-27 | University Of Virginia Patent Foundation | Method to reduce an inflammatory response from arthritis |
| US6232297B1 (en) * | 1999-02-01 | 2001-05-15 | University Of Virginia Patent Foundation | Methods and compositions for treating inflammatory response |
| US7427606B2 (en) * | 1999-02-01 | 2008-09-23 | University Of Virginia Patent Foundation | Method to reduce inflammatory response in transplanted tissue |
| GB0015447D0 (en) * | 2000-06-23 | 2000-08-16 | Pharmacia & Upjohn Spa | Combined therapy against tumors comprising substituted acryloyl derivates and alkylating agents |
| ATE374609T1 (de) | 2000-11-30 | 2007-10-15 | Childrens Medical Center | Synthese von 4-aminothalidomid enantiomeren |
| DK1382604T3 (da) * | 2001-04-27 | 2006-04-18 | Kirin Brewery | Quinolinderivater med en azolylgruppe og quinazolinderivater |
| EP1470119A4 (en) * | 2001-06-13 | 2005-10-19 | Genesoft Pharmaceuticals Inc | BENZOTHIOPHENE COMPOUNDS WITH ANTI-INFECTIOUS ACTIVITY |
| NZ531294A (en) * | 2001-08-06 | 2005-11-25 | Childrens Medical Center | Synthesis and anti-tumor activity of nitrogen substituted thalidomide analogs |
| NZ556354A (en) * | 2001-10-01 | 2008-10-31 | Univ Virginia | 2-Propynyl adenosine analogs having A2A agonist activity and compositions thereof |
| DK1471054T3 (da) * | 2002-01-11 | 2009-11-09 | Daiichi Sankyo Co Ltd | Aminoalkohol-derivat eller phosphonsyre-derivat og medicinsk sammensætning, der indeholder disse |
| NZ549162A (en) | 2004-02-24 | 2009-12-24 | Sankyo Co | Amino-pyrrol alcohol compounds |
| WO2006023272A1 (en) * | 2004-08-02 | 2006-03-02 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having a2a agonist activity |
| AU2005267706B2 (en) * | 2004-08-02 | 2011-12-08 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs with modified 5'-ribose groups having A2A agonist activity |
| US7576069B2 (en) * | 2004-08-02 | 2009-08-18 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having A2A agonist activity |
| US8178509B2 (en) * | 2006-02-10 | 2012-05-15 | University Of Virginia Patent Foundation | Method to treat sickle cell disease |
| US8188063B2 (en) * | 2006-06-19 | 2012-05-29 | University Of Virginia Patent Foundation | Use of adenosine A2A modulators to treat spinal cord injury |
| US8058259B2 (en) * | 2007-12-20 | 2011-11-15 | University Of Virginia Patent Foundation | Substituted 4-{3-[6-amino-9-(3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid esters as A2AR agonists |
| EP3381897A1 (en) | 2017-03-27 | 2018-10-03 | Leadiant Biosciences SA | Derivatives of the disodium 2,2'-{carbonylbis[imino-3,1-phenylenecarbonylimino(1-methyl-1h-pyrrole-4,2-diyl)carbonylimino]}dinaphthalene-1,5-disulfonate salt and related compounds as heparanase inhibitors for the treatment of cancer |
| US12152106B2 (en) | 2020-06-15 | 2024-11-26 | The Government Of The United States Of America, As Represented By The Secretary Of The Navy | Electrically conducting polyamides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2785183A (en) * | 1954-04-19 | 1957-03-12 | American Cyanamid Co | N [4-aminopyrrolyl-2-carbonyl] amino acids |
| US2785182A (en) * | 1954-04-19 | 1957-03-12 | American Cyanamid Co | Substituted pyrrolecarboxamidopyroles |
| CA1308516C (en) * | 1987-07-06 | 1992-10-06 | The Governors Of The University Of Alberta | Oligopeptide anticancer and antiviral agents |
| GB9000644D0 (en) * | 1990-01-11 | 1990-03-14 | Erba Carlo Spa | New ureido derivatives of poly-4-amino-2-carboxy-1-methyl compounds |
| GB9028123D0 (en) * | 1990-12-28 | 1991-02-13 | Erba Carlo Spa | Monoclonal antibodies against human tumor necrosis factor alpha |
-
1990
- 1990-01-11 GB GB909000644A patent/GB9000644D0/en active Pending
-
1991
- 1991-01-03 IL IL9687591A patent/IL96875A/en not_active IP Right Cessation
- 1991-01-07 JP JP03502425A patent/JP3121343B2/ja not_active Expired - Fee Related
- 1991-01-07 HU HU912923A patent/HUT61280A/hu unknown
- 1991-01-07 ES ES91902204T patent/ES2084153T3/es not_active Expired - Lifetime
- 1991-01-07 RU SU915001843A patent/RU2078079C1/ru not_active IP Right Cessation
- 1991-01-07 KR KR1019910701078A patent/KR0176258B1/ko not_active Expired - Fee Related
- 1991-01-07 EP EP91902204A patent/EP0462258B1/en not_active Expired - Lifetime
- 1991-01-07 UA UA5001843A patent/UA32513A/uk unknown
- 1991-01-07 AU AU70599/91A patent/AU647446B2/en not_active Ceased
- 1991-01-07 DE DE69115570T patent/DE69115570T2/de not_active Expired - Fee Related
- 1991-01-07 MX MX9203119A patent/MX9203119A/es unknown
- 1991-01-07 US US07/752,577 patent/US5260329A/en not_active Expired - Lifetime
- 1991-01-07 AT AT91902204T patent/ATE131810T1/de not_active IP Right Cessation
- 1991-01-07 WO PCT/EP1991/000014 patent/WO1991010649A1/en not_active Ceased
- 1991-01-07 DK DK91902204.6T patent/DK0462258T3/da active
- 1991-01-07 NZ NZ236707A patent/NZ236707A/en unknown
- 1991-01-07 CA CA002050331A patent/CA2050331C/en not_active Expired - Fee Related
- 1991-01-09 ZA ZA91177A patent/ZA91177B/xx unknown
- 1991-01-10 IE IE7491A patent/IE69462B1/en not_active IP Right Cessation
- 1991-01-10 YU YU2591A patent/YU48548B/sh unknown
- 1991-01-10 SI SI9110025A patent/SI9110025B/sl unknown
- 1991-01-10 CN CN91100140A patent/CN1032750C/zh not_active Expired - Fee Related
- 1991-01-10 PT PT96455A patent/PT96455B/pt not_active IP Right Cessation
- 1991-01-10 MY MYPI91000036A patent/MY107890A/en unknown
- 1991-01-11 CZ CS9156A patent/CZ285251B6/cs not_active IP Right Cessation
- 1991-01-11 SK SK56-91A patent/SK280190B6/sk unknown
- 1991-09-09 FI FI914251A patent/FI99011C/fi active
- 1991-09-10 NO NO913572A patent/NO176274C/no not_active IP Right Cessation
-
1993
- 1993-03-11 HR HRP-25/91A patent/HRP930311B1/xx not_active IP Right Cessation
- 1993-05-25 US US08/066,583 patent/US5420296A/en not_active Expired - Fee Related
-
1994
- 1994-02-22 BG BG098517A patent/BG60534B2/bg unknown
-
1995
- 1995-04-21 US US08/426,130 patent/US5593976A/en not_active Expired - Fee Related
- 1995-06-30 HU HU95P/P00701P patent/HU211237A9/hu unknown
-
1996
- 1996-01-24 GR GR960400165T patent/GR3018767T3/el unknown
-
1998
- 1998-06-18 HK HK98105643A patent/HK1006455A1/en not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5260329A (en) | Ureido derivatives of poly-4-amino-2-carboxy-1-methyl compounds | |
| HK1006455B (en) | Ureido derivatives of poly-4-amino-2-carboxy-1-methyl compounds | |
| CA2030519C (en) | Acryloyl substituted pyrrole derivatives | |
| EP0915845B1 (en) | Acryloyl substituted distamycin derivatives, process for preparing them, and their use as antitumor and antiviral agents | |
| EP0912509B1 (en) | Distamycin derivatives, process for preparing them, and their use as antitumor and antiviral agents | |
| US5534539A (en) | Biologically active ureido derivatives useful as anit-metastic agenst | |
| EP1100777B1 (en) | Sulfurated distamycin derivatives, process for preparing them, and their use as antitumor agents | |
| MXPA97001949A (en) | Derivatives of distamycine substituted with bis- (2-haloethyl) aminophenylene as anatomy agents yantivira | |
| CA2199635A1 (en) | Bis-(2-haloethyl)aminophenyl substituted distamycin derivatives as antitumor and antiviral agents | |
| EP1084120B1 (en) | Cinnamoyl distamycin analogous derivatives, process for their preparation, and their use as antitumor agents | |
| JPH06184098A (ja) | 治療上有効なナフタレンスルホン系ピロールカルボキサミド誘導体 | |
| AU670194B2 (en) | Biologically active ureido derivatives useful in the treatment of lentivirus-induced disease | |
| WO1999000364A1 (en) | Poly-branched polycarboxamido compounds | |
| GB2260134A (en) | Derivatives of poly-5-amino-3-carboxy-1-methyl compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HC | Change of name of proprietor(s) | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |