AP597A - Retroviral protease inhibitors. - Google Patents
Retroviral protease inhibitors. Download PDFInfo
- Publication number
- AP597A AP597A APAP/P/1994/000667A AP9400667A AP597A AP 597 A AP597 A AP 597A AP 9400667 A AP9400667 A AP 9400667A AP 597 A AP597 A AP 597A
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- ARIPO
- Prior art keywords
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- amino
- previously defined
- hydroxy
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- 230000001177 retroviral effect Effects 0.000 title abstract description 10
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title abstract description 6
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title abstract description 6
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- 125000002619 bicyclic group Chemical group 0.000 claims description 38
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- 125000001424 substituent group Chemical group 0.000 claims description 35
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 235000008390 olive oil Nutrition 0.000 description 1
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- 235000005985 organic acids Nutrition 0.000 description 1
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- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
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- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- FHHJDRFHHWUPDG-UHFFFAOYSA-N peroxysulfuric acid Chemical compound OOS(O)(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-N 0.000 description 1
- KIHQWOBUUIPWAN-UHFFFAOYSA-N phenanthren-9-amine Chemical compound C1=CC=C2C(N)=CC3=CC=CC=C3C2=C1 KIHQWOBUUIPWAN-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
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- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical group 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- FUWGSUOSJRCEIV-UHFFFAOYSA-N phosphonothioic O,O-acid Chemical compound OP(O)=S FUWGSUOSJRCEIV-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
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- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
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- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KYQYHTBRAZHQRJ-HOTGVXAUSA-N tert-butyl n-[[(2s,3s)-3-amino-2-hydroxy-4-phenylbutyl]-propan-2-ylamino]carbamate Chemical compound CC(C)(C)OC(=O)NN(C(C)C)C[C@H](O)[C@@H](N)CC1=CC=CC=C1 KYQYHTBRAZHQRJ-HOTGVXAUSA-N 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical class C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UQCWXKSHRQJGPH-UHFFFAOYSA-M tetrabutylazanium;fluoride;hydrate Chemical compound O.[F-].CCCC[N+](CCCC)(CCCC)CCCC UQCWXKSHRQJGPH-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000001239 threonyl group Chemical group 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- BJBUEDPLEOHJGE-IMJSIDKUSA-N trans-3-hydroxy-L-proline Chemical compound O[C@H]1CC[NH2+][C@@H]1C([O-])=O BJBUEDPLEOHJGE-IMJSIDKUSA-N 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N trans-4-Hydroxy-L-proline Natural products O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- YFNGWGVTFYSJHE-UHFFFAOYSA-K trisodium;phosphonoformate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O.OP(O)(=O)C([O-])=O YFNGWGVTFYSJHE-UHFFFAOYSA-K 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPM116193 | 1993-09-10 | ||
AUPM6446A AUPM644694A0 (en) | 1994-06-24 | 1994-06-24 | Polar-substituted hydrocarbons |
Publications (2)
Publication Number | Publication Date |
---|---|
AP9400667A0 AP9400667A0 (en) | 1994-10-31 |
AP597A true AP597A (en) | 1997-07-15 |
Family
ID=25644541
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
APAP/P/1994/000667A AP597A (en) | 1993-09-10 | 1994-09-09 | Retroviral protease inhibitors. |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP0717736B1 (fr) |
KR (1) | KR100424544B1 (fr) |
CN (1) | CN1144793C (fr) |
AP (1) | AP597A (fr) |
AT (1) | ATE267180T1 (fr) |
CA (1) | CA2171471A1 (fr) |
DE (1) | DE69433793T2 (fr) |
HK (1) | HK1011024A1 (fr) |
IL (1) | IL110898A0 (fr) |
PL (1) | PL313407A1 (fr) |
SK (1) | SK31596A3 (fr) |
TW (1) | TW505636B (fr) |
WO (1) | WO1995007269A1 (fr) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040122000A1 (en) | 1981-01-07 | 2004-06-24 | Vertex Pharmaceuticals Incorporated. | Inhibitors of aspartyl protease |
US6878728B1 (en) | 1999-06-11 | 2005-04-12 | Vertex Pharmaceutical Incorporated | Inhibitors of aspartyl protease |
US5753652A (en) * | 1991-07-03 | 1998-05-19 | Novartis Corporation | Antiretroviral hydrazine derivatives |
US5849911A (en) | 1996-04-22 | 1998-12-15 | Novartis Finance Corporation | Antivirally active heterocyclic azahexane derivatives |
AU2959397A (en) * | 1996-05-31 | 1998-01-05 | Novartis Ag | Process for the preparation of hydrazine derivatives useful as intermediates for the preparation of peptide analogues |
DK0966443T3 (da) | 1997-02-26 | 2009-03-09 | Pfizer | Heteroaryl-hexansyre amidderivater, deres fremstilling og deres anvendelse som selektive inhibitorer af MIP-1-alfa binding til dens CCR1 receptor |
US6436989B1 (en) | 1997-12-24 | 2002-08-20 | Vertex Pharmaceuticals, Incorporated | Prodrugs of aspartyl protease inhibitors |
EP1086076B1 (fr) | 1998-06-19 | 2004-12-22 | Vertex Pharmaceuticals Incorporated | Inhibiteurs sulfonamides d'aspartyle protease |
TNSN00027A1 (fr) | 1999-02-12 | 2005-11-10 | Vertex Pharma | Inhibiteurs de l'aspartyle protease |
CN101423481A (zh) | 2002-04-25 | 2009-05-06 | 小野药品工业株式会社 | 二酮肼衍生物化合物以及含有该化合物作为有效成分的药物 |
CN101023090B (zh) | 2004-07-06 | 2013-03-27 | 雅培制药有限公司 | Hiv蛋白酶抑制剂的前药 |
JP5599611B2 (ja) | 2006-07-21 | 2014-10-01 | ギリアード サイエンシーズ, インコーポレイテッド | 抗ウイルスプロテアーゼインヒビター |
CN104628771B (zh) * | 2014-08-14 | 2016-05-11 | 赫斯(西安)生物科技有限公司 | 抗病毒药物及其药物组合物 |
CN105669749B (zh) * | 2014-08-14 | 2018-03-30 | 赫斯(西安)生物科技有限公司 | 抗病毒药物及组合物 |
KR20180095622A (ko) | 2015-12-18 | 2018-08-27 | 헤래우스 크바르츠글라스 게엠베하 & 컴파니 케이지 | 내화성 금속으로 제조된 용융 도가니에서 실리카 유리 제품의 제조 |
WO2017103125A1 (fr) | 2015-12-18 | 2017-06-22 | Heraeus Quarzglas Gmbh & Co. Kg | Granulation par atomisation de dioxyde de silicium lors de la fabrication de verre de silice |
TWI794150B (zh) | 2015-12-18 | 2023-03-01 | 德商何瑞斯廓格拉斯公司 | 自二氧化矽顆粒製備石英玻璃體 |
CN108698888A (zh) | 2015-12-18 | 2018-10-23 | 贺利氏石英玻璃有限两合公司 | 在石英玻璃制备中作为中间物的经碳掺杂的二氧化硅颗粒的制备 |
US10730780B2 (en) | 2015-12-18 | 2020-08-04 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of a quartz glass body in a multi-chamber oven |
US11952303B2 (en) | 2015-12-18 | 2024-04-09 | Heraeus Quarzglas Gmbh & Co. Kg | Increase in silicon content in the preparation of quartz glass |
TWI813534B (zh) | 2015-12-18 | 2023-09-01 | 德商何瑞斯廓格拉斯公司 | 利用露點監測在熔融烘箱中製備石英玻璃體 |
US11236002B2 (en) | 2015-12-18 | 2022-02-01 | Heraeus Quarzglas Gmbh & Co. Kg | Preparation of an opaque quartz glass body |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992008699A1 (fr) * | 1990-11-19 | 1992-05-29 | Monsanto Company | Inhibiteurs de proteases retrovirales |
WO1992015319A1 (fr) * | 1991-03-08 | 1992-09-17 | Smithkline Beecham Corporation | Agents inhibiteurs de protease de l'hiv |
WO1992022313A1 (fr) * | 1991-06-11 | 1992-12-23 | Abbott Laboratories | Composes inhibant la renine |
Family Cites Families (65)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0395664A1 (fr) * | 1987-10-21 | 1990-11-07 | The Upjohn Company | Inhibiteurs de renine contenant une fraction de (1-amino-2-hydroxy-2-heterocyclique) ethyle |
JPH03504127A (ja) * | 1988-05-03 | 1991-09-12 | ジ・アップジョン・カンパニー | 置換されたフェノキシアセチル基を含有するペプチド類 |
EP0361341A3 (fr) * | 1988-09-28 | 1991-07-03 | Miles Inc. | Agents thérapeutiques contre le SIDA basés sur des inhibiteurs des protéases du HIV |
DE3840452A1 (de) * | 1988-12-01 | 1990-06-07 | Hoechst Ag | (beta)-amino-boronsaeure-derivate |
DE3841520A1 (de) * | 1988-12-09 | 1990-06-13 | Hoechst Ag | Enzymhemmende harnstoffderivate von dipeptiden, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung |
US5215968A (en) * | 1988-12-10 | 1993-06-01 | Hoechst Aktiengesellschaft | Dipeptide derivatives having an enzyme inhibitory action |
DE3842067A1 (de) * | 1988-12-14 | 1990-06-21 | Hoechst Ag | Enzym-hemmende aminosaeurederivate, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung |
US5198426A (en) * | 1988-12-30 | 1993-03-30 | Warner-Lambert Company | Renin inhibitors containing c-terminal dihydroxy amides |
EP0409962B1 (fr) * | 1989-02-10 | 1995-12-06 | SCHRAMM, Wolfgang | Inhibiteur des proteases vih |
DE3913272A1 (de) * | 1989-04-22 | 1990-10-25 | Hoechst Ag | Dipeptid-derivate mit enzym-inhibitorischer wirkung |
US5126326A (en) * | 1989-06-06 | 1992-06-30 | Bio-Mega, Inc. | Enzyme inhibiting peptide derivatives |
US5212157A (en) * | 1989-06-06 | 1993-05-18 | Bio-Mega, Inc. | Enzyme inhibitors |
EP0428849A3 (en) * | 1989-09-28 | 1991-07-31 | Hoechst Aktiengesellschaft | Retroviral protease inhibitors |
DE4033062A1 (de) * | 1990-10-18 | 1992-04-23 | Merck Patent Gmbh | Aminosaeurederivate |
US5221665A (en) * | 1989-10-27 | 1993-06-22 | Boehringer Ingelheim Pharmaceuticals, Inc. | N-substituted amides |
JPH05501879A (ja) * | 1989-10-27 | 1993-04-08 | ジ・アップジョン・カンパニー | Hivおよび他のレトロウイルスを処理する方法およびそれに有用な化合物 |
WO1991008221A1 (fr) * | 1989-12-04 | 1991-06-13 | Wisconsin Alumni Research Foundation | Inhibiteurs de peptides de protease d'hiv |
DE3941235A1 (de) * | 1989-12-14 | 1991-06-20 | Bayer Ag | Neue peptide, ihre herstellung und ihre verwendung in arzneimitteln |
EP0594586A4 (en) * | 1990-01-09 | 1994-08-17 | Smithkline Beecham Corp | Hiv protease inhibitors |
DE4001236A1 (de) * | 1990-01-18 | 1991-07-25 | Bayer Ag | Neue peptide, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel, insbesondere als arzneimittel gegen retroviren |
US5221667A (en) * | 1990-01-22 | 1993-06-22 | Warner-Lambert Company | Renin inhibiting peptides having an α-heteroatom amino acid at the P3 position |
CA2036397C (fr) * | 1990-02-23 | 2000-12-12 | Paul Cates Anderson | Inhibiteurs de la protease du vih, renfermant des unites d'amino-acides |
CA2036398C (fr) * | 1990-02-23 | 2000-06-13 | Boehringer Ingelheim (Canada) Ltd./ Boehringer Ingelheim (Canada) Ltee | Agents d'inhibition de la protease du vih |
CA2036413C (fr) * | 1990-02-23 | 2000-12-12 | Paul Cates Anderson | Inhibiteurs de la protease du vih |
AU8205491A (en) * | 1990-06-01 | 1991-12-31 | Du Pont Merck Pharmaceutical Company, The | 1,4-diamino-2,3-dihydroxybutanes |
WO1991018866A2 (fr) * | 1990-06-01 | 1991-12-12 | The Du Pont Merck Pharmaceutical Company | 1,4-diamino-2,3-dihydroxybutanes |
AU7732691A (en) * | 1990-06-01 | 1991-12-05 | Ciba-Geigy Ag | Hiv protease inhibitors and processes for their preparation |
AU8320691A (en) * | 1990-07-06 | 1992-02-04 | Smithkline Beecham Corporation | Inhibitors of retroviral proteases |
EP0538374A4 (en) * | 1990-07-06 | 1993-05-19 | Smith-Kline Beecham Corporation | Aspartic protease inhibitors |
EP0538383A1 (fr) * | 1990-07-06 | 1993-04-28 | Smithkline Beecham Corporation | Inhibiteurs de proteases aspartiques |
EP0546115A1 (fr) * | 1990-08-24 | 1993-06-16 | The Upjohn Company | Peptides contenant des amino-polyols utilises comme mimes d'etats de transition |
JPH06502403A (ja) * | 1990-10-10 | 1994-03-17 | ジ・アップジョン・カンパニー | 遷移状態インサートとして置換1,4−ジアミンを含有するペプチド |
EP0483403A1 (fr) * | 1990-10-31 | 1992-05-06 | Hoechst Aktiengesellschaft | Dérivés d'amino-acides ayant une activité d'inhibitrice de rénine, leur procédé de préparation et les médicaments les contenant |
ES2151618T3 (es) * | 1990-11-19 | 2001-01-01 | Monsanto Co | Inhibidores de proteasas retrovirales. |
ES2059289T3 (es) * | 1990-11-19 | 1997-10-16 | Monsanto Co | Inhibidores de la proteasa retroviral. |
ATE296626T1 (de) * | 1990-11-19 | 2005-06-15 | Monsanto Co | Retrovirusprotease inhibitoren |
EP0559793A1 (fr) * | 1990-11-30 | 1993-09-15 | Smithkline Beecham Corporation | Inhibiteurs de la protease du vih |
CA2056911C (fr) * | 1990-12-11 | 1998-09-22 | Yuuichi Nagano | Inhibiteurs de la protease de vih |
EP0492136A3 (en) * | 1990-12-20 | 1993-05-26 | American Cyanamid Company | Retroviral protease inhibitors derived from 3-chloro-2-chloromethyl-1-propene |
NZ241099A (en) * | 1991-01-02 | 1994-08-26 | Merrell Dow Pharma | Difluorostatone analogues and derivatives and pharmaceutical compositions |
IE920414A1 (en) * | 1991-02-08 | 1992-08-12 | Sankyo Co | New beta-amino-alpha-hydroxycarboxylic acids and their use |
US5268361A (en) * | 1991-06-07 | 1993-12-07 | Sri International | Hydroxyazido derivatives and related compounds as renin inhibitors |
PL294866A1 (en) * | 1991-06-21 | 1993-05-31 | Hoechst Ag | Method of obtaining novel rennin redtarding heterocyclic compounds |
PL294870A1 (fr) * | 1991-06-21 | 1993-02-08 | Hoechst Ag | |
MX9203836A (es) * | 1991-07-02 | 1993-01-01 | Sandoz Ag | Derivados de acido-4-amino-3-hidroxicarboxilico y proceso para su preparacion. |
EP0521827B1 (fr) * | 1991-07-03 | 1996-09-25 | Ciba-Geigy Ag | Dérivés d'hydrazine pharmacologiquement actives et procédé pour leur préparation |
IE922316A1 (en) * | 1991-07-17 | 1993-01-27 | Smithkline Beecham Corp | Retroviral protease inhibitors |
DE4126485A1 (de) * | 1991-08-10 | 1993-02-11 | Bayer Ag | Trifluormethyl-haltige pseudopeptide |
US5516784A (en) * | 1991-08-13 | 1996-05-14 | Schering Corporation | Anti-HIV (AIDS) agents |
EP0603309A1 (fr) * | 1991-09-11 | 1994-06-29 | Smithkline Beecham Corporation | Isosteres peptidiques contenant un heterocycle utilises comme inhibiteurs du v.i.h. |
EP0532466A3 (en) * | 1991-09-12 | 1993-06-16 | Ciba-Geigy Ag | Derivatives of 5-amino-4-hydroxy-hexanoic acid and their therapeutical use |
US5250563A (en) * | 1991-09-25 | 1993-10-05 | Merck & Co., Inc. | Inhibitors of HIV protease |
FR2683723B1 (fr) * | 1991-11-14 | 1995-05-19 | Mayoly Spindler Laboratoires | Nouveaux medicaments antiviraux actifs sur le virus vih. |
AU681342B2 (en) * | 1992-03-11 | 1997-08-28 | Narhex Limited | Amine derivatives of oxo- and hydroxy-substitued hydrocarbons |
EP0560268B1 (fr) * | 1992-03-13 | 1995-01-04 | Bio-Mega/Boehringer Ingelheim Research Inc. | Dérivés de l'acide pipécolinic comme inhibiteurs de HIV-protéase |
ZA931777B (en) * | 1992-03-13 | 1993-09-23 | Bio Mega Boehringer Ingelheim | Substituted pyrrolidine derivatives as HIV protease inhibitors. |
TW217410B (fr) * | 1992-04-01 | 1993-12-11 | Ciba Geigy | |
EP0574135B1 (fr) * | 1992-05-13 | 1998-11-18 | Japan Energy Corporation | Procédé de préparation de dérivés peptidiques et leurs corps salins |
DE4215874A1 (de) * | 1992-05-14 | 1993-11-18 | Bayer Ag | Dithiolanylglycinhaltige HIV-Proteaseinhibitoren vom Hydroxyethylenisostertyp |
US5296604A (en) * | 1992-05-15 | 1994-03-22 | Miles Inc. | Proline derivatives and compositions for their use as inhibitors of HIV protease |
SI9300288A (sl) * | 1992-06-16 | 1993-12-31 | Hoffmann La Roche | Benzodiazepini |
US5559256A (en) * | 1992-07-20 | 1996-09-24 | E. R. Squibb & Sons, Inc. | Aminediol protease inhibitors |
DE4232173A1 (de) * | 1992-09-25 | 1994-03-31 | Bayer Ag | 5-Oxo-dibenzo(a,d)cyclohepta-1,4-diene |
TW372972B (en) * | 1992-10-23 | 1999-11-01 | Novartis Ag | Antiretroviral acyl compounds |
DE4308096A1 (de) * | 1993-03-13 | 1994-09-15 | Hoechst Ag | Prodrug-Derivate von Enzyminhibitoren mit Hydroxylgruppen, Verfahren zu deren Herstellung und ihre Verwendung |
-
1994
- 1994-09-08 IL IL11089894A patent/IL110898A0/xx unknown
- 1994-09-09 AP APAP/P/1994/000667A patent/AP597A/en active
- 1994-09-09 TW TW083108353A patent/TW505636B/zh not_active IP Right Cessation
- 1994-09-12 DE DE69433793T patent/DE69433793T2/de not_active Expired - Fee Related
- 1994-09-12 CA CA002171471A patent/CA2171471A1/fr not_active Abandoned
- 1994-09-12 SK SK315-96A patent/SK31596A3/sk unknown
- 1994-09-12 KR KR1019960701314A patent/KR100424544B1/ko not_active IP Right Cessation
- 1994-09-12 PL PL94313407A patent/PL313407A1/xx unknown
- 1994-09-12 WO PCT/AU1994/000538 patent/WO1995007269A1/fr active IP Right Grant
- 1994-09-12 AT AT94926731T patent/ATE267180T1/de not_active IP Right Cessation
- 1994-09-12 EP EP94926731A patent/EP0717736B1/fr not_active Expired - Lifetime
- 1994-09-12 CN CNB941941140A patent/CN1144793C/zh not_active Expired - Lifetime
-
1998
- 1998-11-17 HK HK98112089A patent/HK1011024A1/xx not_active IP Right Cessation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1992008699A1 (fr) * | 1990-11-19 | 1992-05-29 | Monsanto Company | Inhibiteurs de proteases retrovirales |
WO1992015319A1 (fr) * | 1991-03-08 | 1992-09-17 | Smithkline Beecham Corporation | Agents inhibiteurs de protease de l'hiv |
WO1992022313A1 (fr) * | 1991-06-11 | 1992-12-23 | Abbott Laboratories | Composes inhibant la renine |
Also Published As
Publication number | Publication date |
---|---|
KR960704863A (ko) | 1996-10-09 |
ATE267180T1 (de) | 2004-06-15 |
CN1144793C (zh) | 2004-04-07 |
AP9400667A0 (en) | 1994-10-31 |
HK1011024A1 (en) | 1999-07-02 |
DE69433793D1 (de) | 2004-06-24 |
EP0717736A4 (fr) | 1996-08-28 |
IL110898A0 (en) | 1994-11-28 |
PL313407A1 (en) | 1996-06-24 |
CN1135212A (zh) | 1996-11-06 |
WO1995007269A1 (fr) | 1995-03-16 |
TW505636B (en) | 2002-10-11 |
CA2171471A1 (fr) | 1995-03-16 |
EP0717736B1 (fr) | 2004-05-19 |
EP0717736A1 (fr) | 1996-06-26 |
DE69433793T2 (de) | 2005-05-04 |
KR100424544B1 (ko) | 2004-07-22 |
SK31596A3 (en) | 1997-01-08 |
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