NO327892B1 - Tropanderivater nyttige i terapi - Google Patents

Tropanderivater nyttige i terapi Download PDF

Info

Publication number: NO327892B1
Authority: NO; Norway
Prior art keywords: compound; formula; pharmaceutically acceptable; acceptable salt; solvate
Prior art date: 2000-05-26

Application number

NO20025227A

Other languages

English (en)

Norwegian (no)

Other versions

NO20025227L (no

NO20025227D0 (no

Inventor

Anthony Wood

David Anthony Price

Blanda Luzia Christa Stammen

Manoussos Perros

Original Assignee

Pfizer

Priority date (The priority date 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 date listed.)

2000-05-26

Filing date

2002-10-31

Publication date

2009-10-12

2000-05-26 Priority claimed from GB0014046A external-priority patent/GB0014046D0/en

2000-06-27 Priority claimed from GB0015835A external-priority patent/GB0015835D0/en

2002-10-31 Application filed by Pfizer filed Critical Pfizer

2002-10-31 Publication of NO20025227L publication Critical patent/NO20025227L/no

2002-10-31 Publication of NO20025227D0 publication Critical patent/NO20025227D0/no

2009-10-12 Publication of NO327892B1 publication Critical patent/NO327892B1/no

Links

238000002560 therapeutic procedure Methods 0.000 title description 10
150000003813 tropane derivatives Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 228
239000000203 mixture Substances 0.000 claims description 70
150000003839 salts Chemical class 0.000 claims description 66
238000006243 chemical reaction Methods 0.000 claims description 41
238000000034 method Methods 0.000 claims description 39
-1 4,4-difluorocyclohexyl Chemical group 0.000 claims description 31
238000011282 treatment Methods 0.000 claims description 28
239000012453 solvate Substances 0.000 claims description 27
239000003814 drug Substances 0.000 claims description 22
125000001153 fluoro group Chemical group F* 0.000 claims description 18
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 12
201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 12
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
229940079593 drug Drugs 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
206010006451 bronchitis Diseases 0.000 claims description 8
208000027866 inflammatory disease Diseases 0.000 claims description 8
210000004072 lung Anatomy 0.000 claims description 8
230000002757 inflammatory effect Effects 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
208000030507 AIDS Diseases 0.000 claims description 6
230000008878 coupling Effects 0.000 claims description 6
238000010168 coupling process Methods 0.000 claims description 6
238000005859 coupling reaction Methods 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
238000006268 reductive amination reaction Methods 0.000 claims description 5
206010006458 Bronchitis chronic Diseases 0.000 claims description 4
206010007558 Cardiac failure chronic Diseases 0.000 claims description 4
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
208000000668 Chronic Pancreatitis Diseases 0.000 claims description 4
206010009900 Colitis ulcerative Diseases 0.000 claims description 4
208000011231 Crohn disease Diseases 0.000 claims description 4
201000003883 Cystic fibrosis Diseases 0.000 claims description 4
206010014561 Emphysema Diseases 0.000 claims description 4
201000009273 Endometriosis Diseases 0.000 claims description 4
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
206010033649 Pancreatitis chronic Diseases 0.000 claims description 4
206010038997 Retroviral infections Diseases 0.000 claims description 4
206010052779 Transplant rejections Diseases 0.000 claims description 4
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 4
201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
208000007451 chronic bronchitis Diseases 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
210000003734 kidney Anatomy 0.000 claims description 4
208000017169 kidney disease Diseases 0.000 claims description 4
201000006417 multiple sclerosis Diseases 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
208000023504 respiratory system disease Diseases 0.000 claims description 4
206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
206010039083 rhinitis Diseases 0.000 claims description 4
206010009137 Chronic sinusitis Diseases 0.000 claims description 3
230000003213 activating effect Effects 0.000 claims description 3
208000027157 chronic rhinosinusitis Diseases 0.000 claims description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 222
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 101
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
239000000243 solution Substances 0.000 description 68
238000002360 preparation method Methods 0.000 description 61
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
239000002904 solvent Substances 0.000 description 44
230000002829 reductive effect Effects 0.000 description 43
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
150000001412 amines Chemical class 0.000 description 31
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
239000007787 solid Substances 0.000 description 27
239000010410 layer Substances 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 26
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 25
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
238000005160 1H NMR spectroscopy Methods 0.000 description 22
239000002253 acid Substances 0.000 description 22
239000012044 organic layer Substances 0.000 description 22
238000010992 reflux Methods 0.000 description 19
239000003054 catalyst Substances 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
102000019034 Chemokines Human genes 0.000 description 13
108010012236 Chemokines Proteins 0.000 description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 12
102100035875 C-C chemokine receptor type 5 Human genes 0.000 description 12
101710149870 C-C chemokine receptor type 5 Proteins 0.000 description 12
241000725303 Human immunodeficiency virus Species 0.000 description 12
239000002002 slurry Substances 0.000 description 12
229910000029 sodium carbonate Inorganic materials 0.000 description 12
235000017550 sodium carbonate Nutrition 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000012267 brine Substances 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
239000006260 foam Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
150000001408 amides Chemical class 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 9
238000004128 high performance liquid chromatography Methods 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
239000000126 substance Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
201000010099 disease Diseases 0.000 description 8
230000000694 effects Effects 0.000 description 8
238000010828 elution Methods 0.000 description 8
239000003112 inhibitor Substances 0.000 description 8
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 8
229960004592 isopropanol Drugs 0.000 description 8
239000000047 product Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
229910052723 transition metal Inorganic materials 0.000 description 8
150000003624 transition metals Chemical class 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
150000001299 aldehydes Chemical class 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
239000003921 oil Substances 0.000 description 7
238000000634 powder X-ray diffraction Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
229920000858 Cyclodextrin Polymers 0.000 description 6
208000031886 HIV Infections Diseases 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
229910052751 metal Chemical class 0.000 description 6
239000002184 metal Chemical class 0.000 description 6
239000000843 powder Substances 0.000 description 6
102000005962 receptors Human genes 0.000 description 6
108020003175 receptors Proteins 0.000 description 6
230000009467 reduction Effects 0.000 description 6
238000006722 reduction reaction Methods 0.000 description 6
239000012321 sodium triacetoxyborohydride Substances 0.000 description 6
229940124597 therapeutic agent Drugs 0.000 description 6
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
102000004274 CCR5 Receptors Human genes 0.000 description 5
108010017088 CCR5 Receptors Proteins 0.000 description 5
102000009410 Chemokine receptor Human genes 0.000 description 5
108050000299 Chemokine receptor Proteins 0.000 description 5
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 5
OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 5
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 5
239000003638 chemical reducing agent Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000006184 cosolvent Substances 0.000 description 5
238000010511 deprotection reaction Methods 0.000 description 5
208000035475 disorder Diseases 0.000 description 5
238000009472 formulation Methods 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
PPJWMNPSKPESFN-UHFFFAOYSA-N n-benzyl-n'-cyclohexylmethanediimine Chemical compound C=1C=CC=CC=1CN=C=NC1CCCCC1 PPJWMNPSKPESFN-UHFFFAOYSA-N 0.000 description 5
239000000137 peptide hydrolase inhibitor Substances 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
208000035473 Communicable disease Diseases 0.000 description 4
208000037357 HIV infectious disease Diseases 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 4
238000003556 assay Methods 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
239000012455 biphasic mixture Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 4
150000004678 hydrides Chemical class 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229940032147 starch Drugs 0.000 description 4
239000008107 starch Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 4
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
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 description 3
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000013543 active substance Substances 0.000 description 3
238000010533 azeotropic distillation Methods 0.000 description 3
239000002775 capsule Substances 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 3
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
239000008101 lactose Substances 0.000 description 3
210000000265 leukocyte Anatomy 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000002674 ointment Substances 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 3
239000012071 phase Substances 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
238000001144 powder X-ray diffraction data Methods 0.000 description 3
230000002265 prevention Effects 0.000 description 3
229910052703 rhodium Inorganic materials 0.000 description 3
239000010948 rhodium Substances 0.000 description 3
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
YHGHRIAZABSSGB-DFNIBXOVSA-N (1s,5r)-8-benzyl-3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane Chemical compound CC(C)C1=NN=C(C)N1C1C[C@H](N2CC=3C=CC=CC=3)CC[C@H]2C1 YHGHRIAZABSSGB-DFNIBXOVSA-N 0.000 description 2
LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 2
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 2
ZJSQZQMVXKZAGW-UHFFFAOYSA-N 2H-benzotriazol-4-ol hydrate Chemical compound O.OC1=CC=CC2=C1N=NN2 ZJSQZQMVXKZAGW-UHFFFAOYSA-N 0.000 description 2
HYIUDFLDFSIXTR-UHFFFAOYSA-N 4,4-difluorocyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(F)(F)CC1 HYIUDFLDFSIXTR-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
102000014150 Interferons Human genes 0.000 description 2
108010050904 Interferons Proteins 0.000 description 2
KJHKTHWMRKYKJE-SUGCFTRWSA-N Kaletra Chemical compound N1([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=2C=CC=CC=2)NC(=O)COC=2C(=CC=CC=2C)C)CC=2C=CC=CC=2)CCCNC1=O KJHKTHWMRKYKJE-SUGCFTRWSA-N 0.000 description 2
102000009571 Macrophage Inflammatory Proteins Human genes 0.000 description 2
108010009474 Macrophage Inflammatory Proteins Proteins 0.000 description 2
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 2
229930040373 Paraformaldehyde Natural products 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
229940124158 Protease/peptidase inhibitor Drugs 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
210000001744 T-lymphocyte Anatomy 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000002648 combination therapy Methods 0.000 description 2
230000000295 complement effect Effects 0.000 description 2
239000006071 cream Substances 0.000 description 2
RHJVIGLEIFVHIJ-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1[CH]CCCC1 RHJVIGLEIFVHIJ-UHFFFAOYSA-N 0.000 description 2
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 description 2
125000005610 enamide group Chemical group 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
238000005469 granulation Methods 0.000 description 2
230000003179 granulation Effects 0.000 description 2
239000001863 hydroxypropyl cellulose Substances 0.000 description 2
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
238000011221 initial treatment Methods 0.000 description 2
229940079322 interferon Drugs 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000006210 lotion Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
KFSOYEAOVNOZNU-UHFFFAOYSA-N n-(8-benzyl-8-azabicyclo[3.2.1]octan-3-ylidene)hydroxylamine Chemical compound C1C(=NO)CC2CCC1N2CC1=CC=CC=C1 KFSOYEAOVNOZNU-UHFFFAOYSA-N 0.000 description 2
239000006199 nebulizer Substances 0.000 description 2
NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 2
239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 2
238000005580 one pot reaction Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
229920002866 paraformaldehyde Polymers 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
210000005105 peripheral blood lymphocyte Anatomy 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
239000003444 phase transfer catalyst Substances 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000004044 response Effects 0.000 description 2
230000001177 retroviral effect Effects 0.000 description 2
229910052707 ruthenium Inorganic materials 0.000 description 2
238000004088 simulation Methods 0.000 description 2
238000009097 single-agent therapy Methods 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
241001430294 unidentified retrovirus Species 0.000 description 2
SYSFTTYJTWPOOR-UHFFFAOYSA-N (2-diphenylphosphanyl-1-naphthalen-1-yl-3h-naphthalen-2-yl)-diphenylphosphane Chemical group C1C=C2C=CC=CC2=C(C=2C3=CC=CC=C3C=CC=2)C1(P(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 SYSFTTYJTWPOOR-UHFFFAOYSA-N 0.000 description 1
SEQXIQNPMQTBGN-VIFPVBQESA-N (3s)-3-amino-3-phenylpropan-1-ol Chemical compound OCC[C@H](N)C1=CC=CC=C1 SEQXIQNPMQTBGN-VIFPVBQESA-N 0.000 description 1
CUFQBQOBLVLKRF-RZDMPUFOSA-N (4r)-3-[(2s,3s)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylbutanoyl]-5,5-dimethyl-n-[(2-methylphenyl)methyl]-1,3-thiazolidine-4-carboxamide Chemical compound CC1=CC=CC=C1CNC(=O)[C@@H]1C(C)(C)SCN1C(=O)[C@@H](O)[C@@H](NC(=O)C=1C(=C(O)C=CC=1)C)CC1=CC=CC=C1 CUFQBQOBLVLKRF-RZDMPUFOSA-N 0.000 description 1
GWKIPRVERALPRD-ZDUSSCGKSA-N (s)-4-isopropoxycarbonyl-6-methoxy-3-methylthiomethyl-3,4-dihydroquinoxalin-2(1h)-thione Chemical compound N1C(=S)[C@H](CSC)N(C(=O)OC(C)C)C2=CC(OC)=CC=C21 GWKIPRVERALPRD-ZDUSSCGKSA-N 0.000 description 1
YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
VRAJWAGCJIXJHQ-WCQYABFASA-N 1-(5-bromopyridin-2-yl)-3-[(1r,2r)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea Chemical compound CCC(=O)C1=CC=C(F)C([C@@H]2[C@@H](C2)NC(=O)NC=2N=CC(Br)=CC=2)=C1O VRAJWAGCJIXJHQ-WCQYABFASA-N 0.000 description 1
NKPHEWJJTGPRSL-GXTWGEPZSA-N 1-(5-cyanopyridin-2-yl)-3-[(1r,2r)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea Chemical compound CCC(=O)C1=CC=C(F)C([C@@H]2[C@@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O NKPHEWJJTGPRSL-GXTWGEPZSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
AJNZWRKTWQLAJK-UHFFFAOYSA-N 1-[2-(2,5-dimethylphospholan-1-yl)phenyl]-2,5-dimethylphospholane Chemical compound CC1CCC(C)P1C1=CC=CC=C1P1C(C)CCC1C AJNZWRKTWQLAJK-UHFFFAOYSA-N 0.000 description 1
OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 description 1
GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 1
BQQVEASFNMRTBA-UHFFFAOYSA-N 2-[4-(3-aminopropyl)piperazin-1-yl]ethanol Chemical compound NCCCN1CCN(CCO)CC1 BQQVEASFNMRTBA-UHFFFAOYSA-N 0.000 description 1
HQWDKLAIDBOLFE-UHFFFAOYSA-M 2-fluoro-1-methylpyridin-1-ium;4-methylbenzenesulfonate Chemical compound C[N+]1=CC=CC=C1F.CC1=CC=C(S([O-])(=O)=O)C=C1 HQWDKLAIDBOLFE-UHFFFAOYSA-M 0.000 description 1
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
PJWULPCWPCVQKD-UHFFFAOYSA-N 4,4-difluorocyclohexane-1-carbonyl chloride Chemical compound FC1(F)CCC(C(Cl)=O)CC1 PJWULPCWPCVQKD-UHFFFAOYSA-N 0.000 description 1
RUEXKRNFAABHHU-UHFFFAOYSA-N 5,5,5-trifluoropentanoic acid Chemical compound OC(=O)CCCC(F)(F)F RUEXKRNFAABHHU-UHFFFAOYSA-N 0.000 description 1
TZWXPIKAEAYGPF-UHFFFAOYSA-N 8-benzyl-8-azabicyclo[3.2.1]octan-3-amine Chemical compound C1C(N)CC2CCC1N2CC1=CC=CC=C1 TZWXPIKAEAYGPF-UHFFFAOYSA-N 0.000 description 1
RSUHKGOVXMXCND-UHFFFAOYSA-N 8-benzyl-8-azabicyclo[3.2.1]octan-3-one Chemical compound C1C(=O)CC2CCC1N2CC1=CC=CC=C1 RSUHKGOVXMXCND-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229920001450 Alpha-Cyclodextrin Polymers 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
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
108700012434 CCL3 Proteins 0.000 description 1
108700011778 CCR5 Proteins 0.000 description 1
108010036239 CD4-IgG(2) Proteins 0.000 description 1
QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 description 1
102000000013 Chemokine CCL3 Human genes 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
229920002785 Croscarmellose sodium Polymers 0.000 description 1
DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 1
XPOQHMRABVBWPR-UHFFFAOYSA-N Efavirenz Natural products O1C(=O)NC2=CC=C(Cl)C=C2C1(C(F)(F)F)C#CC1CC1 XPOQHMRABVBWPR-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
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 1
239000004471 Glycine Substances 0.000 description 1
102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
108010010369 HIV Protease Proteins 0.000 description 1
108010078851 HIV Reverse Transcriptase Proteins 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
206010061598 Immunodeficiency Diseases 0.000 description 1
102000000588 Interleukin-2 Human genes 0.000 description 1
108010002350 Interleukin-2 Proteins 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
229910010199 LiAl Inorganic materials 0.000 description 1
240000003183 Manihot esculenta Species 0.000 description 1
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
238000006683 Mannich reaction Methods 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
101100189356 Mus musculus Papolb gene Proteins 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
229910019093 NaOCl Inorganic materials 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
208000001388 Opportunistic Infections Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
239000004147 Sorbitan trioleate Substances 0.000 description 1
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 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
QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
102000007124 Tachykinin Receptors Human genes 0.000 description 1
108010072901 Tachykinin Receptors Proteins 0.000 description 1
SUJUHGSWHZTSEU-UHFFFAOYSA-N Tipranavir Natural products C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 SUJUHGSWHZTSEU-UHFFFAOYSA-N 0.000 description 1
206010058874 Viraemia Diseases 0.000 description 1
208000036142 Viral infection Diseases 0.000 description 1
WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
IBHARWXWOCPXCR-WELGVCPWSA-N [(2s,3s,5r)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl (2-decoxy-3-dodecylsulfanylpropyl) hydrogen phosphate Chemical compound C1[C@H](N=[N+]=[N-])[C@@H](COP(O)(=O)OCC(CSCCCCCCCCCCCC)OCCCCCCCCCC)O[C@H]1N1C(=O)NC(=O)C(C)=C1 IBHARWXWOCPXCR-WELGVCPWSA-N 0.000 description 1
KCHSXTFENLKRNX-UHFFFAOYSA-N [2-bis(4-methylphenyl)phosphanyl-1-naphthalen-1-yl-3h-naphthalen-2-yl]-bis(4-methylphenyl)phosphane Chemical group C1=CC(C)=CC=C1P(C1(C(=C2C=CC=CC2=CC1)C=1C2=CC=CC=C2C=CC=1)P(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 KCHSXTFENLKRNX-UHFFFAOYSA-N 0.000 description 1
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
229960004748 abacavir Drugs 0.000 description 1
MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
229960001997 adefovir Drugs 0.000 description 1
WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 description 1
238000011360 adjunctive therapy Methods 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
229960001830 amprenavir Drugs 0.000 description 1
YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
238000011225 antiretroviral therapy Methods 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000011324 bead Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
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 1
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229960003563 calcium carbonate Drugs 0.000 description 1
XAAHAAMILDNBPS-UHFFFAOYSA-L calcium hydrogenphosphate dihydrate Chemical compound O.O.[Ca+2].OP([O-])([O-])=O XAAHAAMILDNBPS-UHFFFAOYSA-L 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 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
229940081733 cetearyl alcohol Drugs 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000002556 chemokine receptor agonist Substances 0.000 description 1
239000002559 chemokine receptor antagonist Substances 0.000 description 1
239000005482 chemotactic factor Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
229940001468 citrate Drugs 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000011284 combination treatment Methods 0.000 description 1
230000009918 complex formation Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
229960001681 croscarmellose sodium Drugs 0.000 description 1
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000009109 curative therapy Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
NXWBOAQGGZVKBT-UHFFFAOYSA-N cyclobutanecarboxamide Chemical compound NC(=O)C1C[CH]C1 NXWBOAQGGZVKBT-UHFFFAOYSA-N 0.000 description 1
TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
229940097362 cyclodextrins Drugs 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
229960005319 delavirdine Drugs 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000011928 denatured alcohol Substances 0.000 description 1
239000007933 dermal patch Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
229940095079 dicalcium phosphate anhydrous Drugs 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
229940042935 dichlorodifluoromethane Drugs 0.000 description 1
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
229960002656 didanosine Drugs 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000007907 direct compression Methods 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000007908 dry granulation Methods 0.000 description 1
229940112141 dry powder inhaler Drugs 0.000 description 1
239000000975 dye Substances 0.000 description 1
XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 1
229960003804 efavirenz Drugs 0.000 description 1
MLILORUFDVLTSP-UHFFFAOYSA-N emivirine Chemical compound O=C1NC(=O)N(COCC)C(CC=2C=CC=CC=2)=C1C(C)C MLILORUFDVLTSP-UHFFFAOYSA-N 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000008387 emulsifying waxe Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
FYXMBQHPFFJHKH-HNNXBMFYSA-N ethyl (3s)-3-[(4,4-difluorocyclohexanecarbonyl)amino]-3-phenylpropanoate Chemical compound N([C@@H](CC(=O)OCC)C=1C=CC=CC=1)C(=O)C1CCC(F)(F)CC1 FYXMBQHPFFJHKH-HNNXBMFYSA-N 0.000 description 1
ATSZQDTVNRNXKB-PPHPATTJSA-N ethyl (3s)-3-amino-3-phenylpropanoate;hydrochloride Chemical compound Cl.CCOC(=O)C[C@H](N)C1=CC=CC=C1 ATSZQDTVNRNXKB-PPHPATTJSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
LLYJISDUHFXOHK-GOCONZMPSA-N ferroptocide Chemical compound C[C@@H]1CC[C@@]23C[C@@H](C(=O)[C@]2([C@@]1([C@@H](C[C@H]([C@@H]3C)C4=CCN5C(=O)N(C(=O)N5C4)C6=CC=CC=C6)OC(=O)CCl)C)O)O LLYJISDUHFXOHK-GOCONZMPSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
229950011117 fozivudine tidoxil Drugs 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000000446 fuel Substances 0.000 description 1
229940050411 fumarate Drugs 0.000 description 1
230000004927 fusion Effects 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
229940049654 glyceryl behenate Drugs 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000005828 hydrofluoroalkanes Chemical class 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000000852 hydrogen donor Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
229960001330 hydroxycarbamide Drugs 0.000 description 1
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
239000002955 immunomodulating agent Substances 0.000 description 1
229940121354 immunomodulator Drugs 0.000 description 1
230000002584 immunomodulator Effects 0.000 description 1
229960001936 indinavir Drugs 0.000 description 1
CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229940124524 integrase inhibitor Drugs 0.000 description 1
239000002850 integrase inhibitor Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940001447 lactate Drugs 0.000 description 1
229960001375 lactose Drugs 0.000 description 1
229960001627 lamivudine Drugs 0.000 description 1
JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 1
239000003446 ligand Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
229960004525 lopinavir Drugs 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
XKIOBYHZFPTKCZ-VIFPVBQESA-N methyl (3s)-3-amino-3-phenylpropanoate Chemical compound COC(=O)C[C@H](N)C1=CC=CC=C1 XKIOBYHZFPTKCZ-VIFPVBQESA-N 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
ABOGULQHPLDMLL-UHFFFAOYSA-N n-(8-benzyl-8-azabicyclo[3.2.1]octan-3-yl)-2-methylpropanamide Chemical compound C1C(NC(=O)C(C)C)CC2CCC1N2CC1=CC=CC=C1 ABOGULQHPLDMLL-UHFFFAOYSA-N 0.000 description 1
YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960000884 nelfinavir Drugs 0.000 description 1
QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 description 1
229960000689 nevirapine Drugs 0.000 description 1
229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
150000003833 nucleoside derivatives Chemical class 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 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
210000000056 organ Anatomy 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000002638 palliative care Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
230000037361 pathway Effects 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
YIQPUIGJQJDJOS-UHFFFAOYSA-N plerixafor Chemical compound C=1C=C(CN2CCNCCCNCCNCCC2)C=CC=1CN1CCCNCCNCCCNCC1 YIQPUIGJQJDJOS-UHFFFAOYSA-N 0.000 description 1
229960002169 plerixafor Drugs 0.000 description 1
230000010287 polarization Effects 0.000 description 1
239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
229940113124 polysorbate 60 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
235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
230000000541 pulsatile effect Effects 0.000 description 1
230000006340 racemization Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 1
230000010076 replication Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229960000311 ritonavir Drugs 0.000 description 1
NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 1
229960001852 saquinavir Drugs 0.000 description 1
QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 1
229960002530 sargramostim Drugs 0.000 description 1
108010038379 sargramostim Proteins 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 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
229960001790 sodium citrate Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
229960001203 stavudine Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229950002920 talviraline Drugs 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical compound OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 description 1
TYYCBAISLMKLMT-UHFFFAOYSA-N tert-butyl 3-amino-3-phenylpropanoate Chemical compound CC(C)(C)OC(=O)CC(N)C1=CC=CC=C1 TYYCBAISLMKLMT-UHFFFAOYSA-N 0.000 description 1
ZGPCDZZHEWGTEU-LBPRGKRZSA-N tert-butyl n-[(1s)-3-oxo-1-phenylpropyl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](CC=O)C1=CC=CC=C1 ZGPCDZZHEWGTEU-LBPRGKRZSA-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
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
SUJUHGSWHZTSEU-FYBSXPHGSA-N tipranavir Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)=C(O)C1)CC1=CC=CC=C1 SUJUHGSWHZTSEU-FYBSXPHGSA-N 0.000 description 1
229960000838 tipranavir Drugs 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
230000006490 viral transcription Effects 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
229960000523 zalcitabine Drugs 0.000 description 1
229960002555 zidovudine Drugs 0.000 description 1
HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- A61P27/16—Otologicals
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Immunology (AREA)
Pulmonology (AREA)
Diabetes (AREA)
Cardiology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Virology (AREA)
Obesity (AREA)
Hospice & Palliative Care (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Hematology (AREA)
Endocrinology (AREA)
Physical Education & Sports Medicine (AREA)
Urology & Nephrology (AREA)
Heart & Thoracic Surgery (AREA)
Rheumatology (AREA)
Molecular Biology (AREA)
Orthopedic Medicine & Surgery (AREA)
AIDS & HIV (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Emergency Medicine (AREA)
Transplantation (AREA)

NO20025227A 2000-05-26 2002-10-31 Tropanderivater nyttige i terapi NO327892B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB0014046A GB0014046D0 (en)	2000-05-26	2000-05-26	Compounds useful in therapy
GB0015835A GB0015835D0 (en)	2000-06-27	2000-06-27	Compounds useful in therapy
PCT/IB2001/000806 WO2001090106A2 (en)	2000-05-26	2001-05-09	Tryasolyl tropane derivatives as ccr5 modulators

Publications (3)

Publication Number	Publication Date
NO20025227L NO20025227L (no)	2002-10-31
NO20025227D0 NO20025227D0 (no)	2002-10-31
NO327892B1 true NO327892B1 (no)	2009-10-12

Family

ID=26244452

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
NO20025227A NO327892B1 (no)	2000-05-26	2002-10-31	Tropanderivater nyttige i terapi
NO2010007C NO2010007I2 (no)	2000-05-26	2010-04-08	N-(IS)-3-I3-isopropyl-5-metyl-4H-1,2,4-triasol-4-yl)-exo-8-azabicyklo[3.2.1]okt-8-yl]-1-fenylpropyl-4,4-difluorcykloheksankarboksamid
NO2020019C NO2020019I1 (no)	2000-05-26	2020-06-30	Maraviroc eventuelt i form av et farmasøytisk akseptabelt salt

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
NO2010007C NO2010007I2 (no)	2000-05-26	2010-04-08	N-(IS)-3-I3-isopropyl-5-metyl-4H-1,2,4-triasol-4-yl)-exo-8-azabicyklo[3.2.1]okt-8-yl]-1-fenylpropyl-4,4-difluorcykloheksankarboksamid
NO2020019C NO2020019I1 (no)	2000-05-26	2020-06-30	Maraviroc eventuelt i form av et farmasøytisk akseptabelt salt

Country Status (51)

Country	Link
EP (3)	EP1284974B1 (de)
JP (2)	JP3693957B2 (de)
KR (2)	KR100523501B1 (de)
CN (2)	CN100355753C (de)
AP (1)	AP1965A (de)
AR (2)	AR028622A1 (de)
AT (2)	ATE260914T1 (de)
AU (2)	AU2001252482B2 (de)
BG (1)	BG65966B1 (de)
BR (1)	BRPI0110955B8 (de)
CA (1)	CA2408909C (de)
CR (1)	CR10145A (de)
CU (1)	CU23288B7 (de)
CY (3)	CY2008006I1 (de)
CZ (1)	CZ299102B6 (de)
DE (3)	DE60102233T2 (de)
DK (2)	DK1526134T3 (de)
DZ (1)	DZ3464A1 (de)
EA (2)	EA007580B1 (de)
EE (1)	EE05110B1 (de)
EG (1)	EG24137A (de)
ES (3)	ES2311126T3 (de)
FR (1)	FR08C0007I2 (de)
GE (1)	GEP20063799B (de)
HK (3)	HK1054927A1 (de)
HR (1)	HRP20020938B1 (de)
HU (1)	HU225810B1 (de)
IL (2)	IL152531A0 (de)
IS (1)	IS2511B (de)
LT (1)	LTC1284974I2 (de)
LU (1)	LU91417I2 (de)
MA (1)	MA26902A1 (de)
ME (1)	ME00555A (de)
MX (1)	MXPA02011631A (de)
MY (3)	MY156920A (de)
NL (1)	NL300338I2 (de)
NO (3)	NO327892B1 (de)
NZ (1)	NZ521477A (de)
OA (1)	OA12264A (de)
PA (1)	PA8517101A1 (de)
PE (1)	PE20011371A1 (de)
PL (1)	PL200551B1 (de)
PT (2)	PT1284974E (de)
RS (2)	RS50904B (de)
SI (2)	SI1526134T1 (de)
SK (1)	SK286129B6 (de)
TN (1)	TNSN01077A1 (de)
TR (1)	TR200400541T4 (de)
TW (1)	TWI230160B (de)
UY (1)	UY26727A1 (de)
WO (1)	WO2001090106A2 (de)

Families Citing this family (40)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GEP20063799B (en) *	2000-05-26	2006-04-25	Pfizer	Tropane derivatives useful in therapy
RU2003137766A (ru) *	2001-06-12	2005-05-20	Ск Корпорейшн (Kr)	Новые фенилалкильные аналоги диаминов и амидов
SE0200919D0 (sv) *	2002-03-25	2002-03-25	Astrazeneca Ab	Chemical compounds
GB0208071D0 (en) *	2002-04-08	2002-05-22	Pfizer Ltd	Tropane derivatives useful in therapy
WO2003084954A1 (en) *	2002-04-08	2003-10-16	Pfizer Limited	Tropane derivatives as ccr5 modulators
US6855724B2 (en)	2002-04-08	2005-02-15	Agouron Pharmaceuticals, Inc.	Tropane derivatives useful in therapy
BR0309982A (pt) *	2002-05-23	2005-03-22	Pfizer	Método para identificação de um ligando, pelo qual o tempo de residência no receptor é medido
WO2004054581A2 (en) *	2002-12-13	2004-07-01	Smithkline Beecham Corporation	Cyclohexyl compounds as ccr5 antagonists
DE10336274A1 (de) *	2003-08-07	2005-03-10	Honeywell Specialty Chemicals	Verfahren zur Herstellung von geminalen Difluoralkanen
NZ545748A (en)	2003-08-29	2010-03-26	Ranbaxy Lab Ltd	Isoxazoline derivatives as inhibitors of phosphodiesterase type-IV
EP1786816A4 (de)	2003-09-10	2009-11-04	Virochem Pharma Inc	Spirohydantoinverbindungen und -verfahren zur modulation von chemokin-rezeptoraktivität
PL1682545T3 (pl)	2003-10-03	2008-04-30	Pfizer	Podstawione imidazopirydyną pochodne tropanu o aktywności antagonisty receptora ccr5 do leczenia hiv i stanu zapalnego
TW200610761A (en) *	2004-04-23	2006-04-01	Astrazeneca Ab	Chemical compounds
RU2006146608A (ru)	2004-06-09	2008-07-20	Ф.Хоффманн-Ля Рош Аг (Ch)	ОКТАГИДРОПИРРОЛО[3,4-с]-ПРОИЗВОДНЫЕ И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ПРОТИВОВИРУСНЫХ АГЕНТОВ
CA2586231A1 (en) *	2004-11-19	2006-05-26	Boehringer Ingelheim International Gmbh	Method for treating hiv infection through co-administration of tipranavir and uk-427, 857
WO2006064340A2 (en) *	2004-12-13	2006-06-22	Pfizer Limited	Process for the preparation of n-acyl beta-aminoaldehydes
US7665658B2 (en)	2005-06-07	2010-02-23	First Data Corporation	Dynamic aggregation of payment transactions
MX2008000984A (es)	2005-07-22	2008-04-04	Progenics Pharm Inc	Metodos para reducir la carga viral en pacientes infectados con vih-1.
CN101291905A (zh)	2005-10-19	2008-10-22	弗·哈夫曼-拉罗切有限公司	苯乙酰胺nnrt抑制剂
AU2007286345B2 (en)	2006-08-16	2012-03-08	F. Hoffmann-La Roche Ag	Non-nucleoside reverse transcriptase inhibitors
US7932235B2 (en)	2006-11-17	2011-04-26	Concert Pharmaceuticals, Inc.	Triazolyl tropane derivatives
ES2550152T3 (es)	2006-12-13	2015-11-04	F. Hoffmann-La Roche Ag	Derivados de 2-(piperidin-4-il)-4-fenoxi-o fenilamino-pirimidina como inhibidores no nucleósidos de transcriptasa inversa
AU2007333667A1 (en) *	2006-12-19	2008-06-26	Auspex Pharmaceuticals, Inc.	Preperation and utility of CCR5 inhibitors
US20080207659A1 (en)	2007-02-15	2008-08-28	Asit Kumar Chakraborti	Inhibitors of phosphodiesterase type 4
WO2008132128A2 (en) *	2007-04-27	2008-11-06	Solvay (Société Anonyme)	Synthesis of a pharmaceutically active compound
US20110059154A1 (en) *	2008-02-29	2011-03-10	Strizki Julie M	Ccr5 antagonists as prophylactics for preventing hiv infection and methods of inhibiting transmission of same
CN101712679B (zh) *	2008-10-08	2013-04-10	中国科学院上海药物研究所	一种酰胺类化合物、其药物组合物及其制备方法和用途
US8592395B2 (en) *	2009-07-24	2013-11-26	Glaxosmithkline Llc	Therapeutic compounds
CN102140104B (zh) *	2010-02-03	2014-11-12	中国科学院上海药物研究所	1-(3-(s)-氨基丙基)-哌啶-4-氨基酰胺类化合物、其药物组合物及其制备方法和用途
BR112012024522A2 (pt)	2010-04-02	2017-08-08	Phivco 1 Llc	combinação, uso de uma combinação, composição farmacêutica, forma de dosagem única , kit, e, método para tratar um distúrbio
CN106977511B (zh) *	2011-12-19	2019-04-12	中国科学院上海药物研究所	一种氨基丙基取代托烷胺类化合物、其药物组合物及其制备方法和用途
EP2912047B1 (de)	2012-10-29	2016-08-24	Cipla Limited	Antivirale phosphonatanaloga und verfahren zur herstellung davon
CZ306455B6 (cs)	2013-04-26	2017-02-01	Zentiva, K.S.	Nový způsob syntézy Maravirocu
CN103497164B (zh) *	2013-09-23	2015-12-23	西安近代化学研究所	一种蒽衍生物及其制备方法
CN104304248B (zh) *	2014-10-23	2016-08-10	西北农林科技大学	3-芳基丙酸酯类化合物作为制备杀螨药物的应用
CN104402883B (zh) *	2014-10-24	2016-04-27	艾琪康医药科技（上海）有限公司	4，4-二氟金刚烷甲酰胺衍生物、药物组合物及其制备方法和用途
CN104387379B (zh) *	2014-11-26	2017-01-11	扬州氟药科技有限公司	一种二氟亚甲基哌啶甲酰胺衍生物及其制备方法和用途
CN104860946A (zh) *	2015-05-14	2015-08-26	湖北生物医药产业技术研究院有限公司	Ccr5拮抗剂的制备方法
CN107879963A (zh) *	2016-09-29	2018-04-06	中国科学院上海药物研究所	新型手性配体、金属螯合物、多种非天然氨基酸、马拉维诺及其关键中间体的合成方法
US11629196B2 (en)	2020-04-27	2023-04-18	Incelldx, Inc.	Method of treating SARS-CoV-2-associated hypercytokinemia by administering a human monoclonal antibody (PRO-140) that inhibits CCR5/CCL5 binding interactions

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5376645A (en)	1990-01-23	1994-12-27	University Of Kansas	Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof
KR0166088B1 (ko)	1990-01-23	1999-01-15	.	수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도
US5648511A (en) *	1990-11-19	1997-07-15	G.D. Searle & Co.	Method for making intermediates useful in the synthesis of retroviral protease inhibitors
FR2676444B1 (fr) *	1991-05-16	1995-03-10	Sanofi Elf	Nouveaux derives d'amino-3 pyridazines actifs sur le systeme nerveux central, procede de preparation et compositions pharmaceutiques en contenant.
GB9310713D0 (en) *	1993-05-24	1993-07-07	Zeneca Ltd	Aryl substituted heterocycles
SK280875B6 (sk) *	1994-04-19	2000-08-14	Neurosearch A/S	Tropánové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a použitie týchto derivátov na výrobu liečiv
GB9523526D0 (en) *	1995-11-17	1996-01-17	Zeneca Ltd	Therapeutic compounds
DE19546462A1 (de) *	1995-12-13	1997-06-19	Bayer Ag	Diarylacetylenketone
AU1208397A (en) *	1995-12-28	1997-07-28	Takeda Chemical Industries Ltd.	Diphenylmethane derivatives as mip-1alpha/rantes receptor antagonists
US6323206B1 (en) *	1996-07-12	2001-11-27	Millennium Pharmaceuticals, Inc.	Chemokine receptor antagonists and methods of use therefor
AU729415B2 (en) *	1996-07-12	2001-02-01	Millennium Pharmaceuticals, Inc.	Chemokine receptor antagonists and methods of use therefor
AU5604998A (en) *	1996-12-13	1998-07-03	Merck & Co., Inc.	Spiro-substituted azacycles as modulators of chemokine receptor activity
WO1998025617A1 (en)	1996-12-13	1998-06-18	Merck & Co., Inc.	Substituted aryl piperazines as modulators of chemokine receptor activity
GB9711643D0 (en)	1997-06-05	1997-07-30	Janssen Pharmaceutica Nv	Glass thermoplastic systems
WO1999004794A1 (en) *	1997-07-25	1999-02-04	Merck & Co., Inc.	Cyclic amine modulators of chemokine receptor activity
IL125658A0 (en) *	1997-08-18	1999-04-11	Hoffmann La Roche	Ccr-3 receptor antagonists
AR013669A1 (es) *	1997-10-07	2001-01-10	Smithkline Beecham Corp	Compuestos y metodos
AU2335699A (en) *	1998-01-21	1999-08-09	Kyowa Hakko Kogyo Co. Ltd.	Chemokine receptor antagonists and methods of use therefor
PE20001420A1 (es) *	1998-12-23	2000-12-18	Pfizer	Moduladores de ccr5
US7217714B1 (en) *	1998-12-23	2007-05-15	Agouron Pharmaceuticals, Inc.	CCR5 modulators
EP1013276A1 (de)	1998-12-23	2000-06-28	Pfizer Inc.	Aminoazacycloalkane als CCR5-Modulatoren
GEP20063799B (en) *	2000-05-26	2006-04-25	Pfizer	Tropane derivatives useful in therapy

2001
- 2001-05-09 GE GEAP2001004960 patent/GEP20063799B/en unknown
- 2001-05-09 SI SI200130862T patent/SI1526134T1/sl unknown
- 2001-05-09 DK DK04004193T patent/DK1526134T3/da active
- 2001-05-09 JP JP2001586293A patent/JP3693957B2/ja not_active Expired - Lifetime
- 2001-05-09 CN CNB2005100068151A patent/CN100355753C/zh not_active Expired - Lifetime
- 2001-05-09 EE EEP200200656A patent/EE05110B1/xx active Protection Beyond IP Right Term
- 2001-05-09 ES ES04004193T patent/ES2311126T3/es not_active Expired - Lifetime
- 2001-05-09 PT PT01925808T patent/PT1284974E/pt unknown
- 2001-05-09 AT AT01925808T patent/ATE260914T1/de active
- 2001-05-09 RS YUP82202 patent/RS50904B/sr unknown
- 2001-05-09 AU AU2001252482A patent/AU2001252482B2/en not_active Expired
- 2001-05-09 AT AT04004193T patent/ATE407134T1/de active
- 2001-05-09 IL IL15253101A patent/IL152531A0/xx unknown
- 2001-05-09 EA EA200401056A patent/EA007580B1/ru not_active IP Right Cessation
- 2001-05-09 ES ES01925808T patent/ES2215129T3/es not_active Expired - Lifetime
- 2001-05-09 HU HU0302474A patent/HU225810B1/hu active Protection Beyond IP Right Term
- 2001-05-09 RS RSP-2009/0438A patent/RS51436B/en unknown
- 2001-05-09 PL PL359267A patent/PL200551B1/pl unknown
- 2001-05-09 TR TR200400541T patent/TR200400541T4/xx unknown
- 2001-05-09 AU AU5248201A patent/AU5248201A/xx active Pending
- 2001-05-09 PT PT04004193T patent/PT1526134E/pt unknown
- 2001-05-09 DE DE2001602233 patent/DE60102233T2/de not_active Expired - Lifetime
- 2001-05-09 ES ES08163025T patent/ES2401812T3/es not_active Expired - Lifetime
- 2001-05-09 WO PCT/IB2001/000806 patent/WO2001090106A2/en active IP Right Grant
- 2001-05-09 KR KR10-2002-7015934A patent/KR100523501B1/ko active IP Right Grant
- 2001-05-09 CA CA 2408909 patent/CA2408909C/en not_active Expired - Lifetime
- 2001-05-09 OA OA1200200343A patent/OA12264A/en unknown
- 2001-05-09 EP EP20010925808 patent/EP1284974B1/de not_active Expired - Lifetime
- 2001-05-09 CN CNB018088287A patent/CN1279040C/zh not_active Expired - Lifetime
- 2001-05-09 DZ DZ013464A patent/DZ3464A1/fr active
- 2001-05-09 BR BRPI0110955A patent/BRPI0110955B8/pt not_active IP Right Cessation
- 2001-05-09 EP EP20080163025 patent/EP1990341B1/de not_active Expired - Lifetime
- 2001-05-09 ME MEP-693/08A patent/ME00555A/xx unknown
- 2001-05-09 KR KR1020057003492A patent/KR100548854B1/ko active IP Right Grant
- 2001-05-09 AP APAP/P/2002/002663A patent/AP1965A/en active
- 2001-05-09 MX MXPA02011631A patent/MXPA02011631A/es active IP Right Grant
- 2001-05-09 SK SK1643-2002A patent/SK286129B6/sk active Protection Beyond IP Right Term
- 2001-05-09 EP EP20040004193 patent/EP1526134B1/de not_active Expired - Lifetime
- 2001-05-09 SI SI200130090T patent/SI1284974T1/xx unknown
- 2001-05-09 NZ NZ521477A patent/NZ521477A/en not_active IP Right Cessation
- 2001-05-09 EA EA200201141A patent/EA005382B1/ru not_active IP Right Cessation
- 2001-05-09 DE DE200812000011 patent/DE122008000011I1/de active Pending
- 2001-05-09 CZ CZ20023806A patent/CZ299102B6/cs not_active IP Right Cessation
- 2001-05-09 DK DK01925808T patent/DK1284974T3/da active
- 2001-05-09 DE DE60135685T patent/DE60135685D1/de not_active Expired - Lifetime
- 2001-05-21 TW TW90112055A patent/TWI230160B/zh active
- 2001-05-22 PA PA8517101A patent/PA8517101A1/es unknown
- 2001-05-22 EG EG20010535A patent/EG24137A/xx active
- 2001-05-23 MY MYPI20094132A patent/MY156920A/en unknown
- 2001-05-23 MY MYPI20041980 patent/MY153023A/en unknown
- 2001-05-23 MY MYPI20012461 patent/MY131019A/en unknown
- 2001-05-24 PE PE2001000476A patent/PE20011371A1/es active IP Right Grant
- 2001-05-24 AR ARP010102486 patent/AR028622A1/es active IP Right Grant
- 2001-05-24 UY UY26727A patent/UY26727A1/es not_active IP Right Cessation
- 2001-05-25 TN TNSN01077 patent/TNSN01077A1/fr unknown
2002
- 2002-09-23 BG BG107140A patent/BG65966B1/bg unknown
- 2002-09-24 IS IS6565A patent/IS2511B/is unknown
- 2002-10-28 IL IL152531A patent/IL152531A/en active Protection Beyond IP Right Term
- 2002-10-28 CU CU20020243A patent/CU23288B7/es unknown
- 2002-10-31 NO NO20025227A patent/NO327892B1/no not_active IP Right Cessation
- 2002-11-14 MA MA26910A patent/MA26902A1/fr unknown
- 2002-11-26 HR HR20020938A patent/HRP20020938B1/xx not_active IP Right Cessation
2003
- 2003-09-30 HK HK03107045A patent/HK1054927A1/xx not_active IP Right Cessation
2005
- 2005-02-15 JP JP2005038062A patent/JP4854970B2/ja not_active Expired - Lifetime
- 2005-11-18 HK HK05110416A patent/HK1078573A1/xx not_active IP Right Cessation
2006
- 2006-10-18 HK HK06111446A patent/HK1090836A1/xx not_active IP Right Cessation
2007
- 2007-03-27 AR ARP070101273 patent/AR060159A2/es unknown
2008
- 2008-02-22 NL NL300338C patent/NL300338I2/nl unknown
- 2008-02-22 LU LU91417C patent/LU91417I2/fr unknown
- 2008-02-25 LT LTPA2008004C patent/LTC1284974I2/lt unknown
- 2008-03-04 FR FR08C0007C patent/FR08C0007I2/fr active Active
- 2008-03-17 CY CY200800006C patent/CY2008006I1/el unknown
- 2008-07-16 CR CR10145A patent/CR10145A/es unknown
- 2008-10-24 CY CY081101203T patent/CY1108451T1/el unknown
2010
- 2010-04-08 NO NO2010007C patent/NO2010007I2/no unknown
2020
- 2020-06-30 NO NO2020019C patent/NO2020019I1/no not_active IP Right Cessation
2022
- 2022-04-19 CY CY2022009C patent/CY2022009I1/el unknown

Also Published As

Publication number	Publication date
IL152531A (en)	2010-05-17
AU5248201A (en)	2001-12-03
ME00555B (me)	2011-12-20
NO2010007I2 (no)	2013-09-09
MXPA02011631A (es)	2003-03-27
ME00555A (en)	2011-12-20
DK1284974T3 (da)	2004-06-07
ES2311126T3 (es)	2009-02-01
AU2001252482B2 (en)	2006-01-19
YU82202A (sh)	2005-11-28
BRPI0110955B1 (pt)	2016-06-28
LTPA2008004I1 (lt)	2020-07-27
CY2008006I2 (el)	2009-11-04
MA26902A1 (fr)	2004-12-20
AP2002002663A0 (en)	2002-12-31
LTC1284974I2 (lt)	2020-11-10
CY2008006I1 (el)	2009-11-04
HUP0302474A2 (hu)	2003-11-28
TR200400541T4 (tr)	2004-04-21
CU23288B7 (es)	2008-06-30
AR060159A2 (es)	2008-05-28
PT1526134E (pt)	2008-10-28
CY1108451T1 (el)	2014-04-09
ES2401812T3 (es)	2013-04-24
PE20011371A1 (es)	2002-01-18
HU225810B1 (en)	2007-10-29
SK16432002A3 (sk)	2004-01-08
LU91417I9 (de)	2019-01-02
CZ20023806A3 (cs)	2004-01-14
ATE260914T1 (de)	2004-03-15
EP1526134B1 (de)	2008-09-03
LU91417I2 (fr)	2008-04-22
FR08C0007I2 (fr)	2009-01-15
MY131019A (en)	2007-07-31
EP1284974B1 (de)	2004-03-03
FR08C0007I1 (de)	2008-04-25
DE60135685D1 (de)	2008-10-16
CA2408909A1 (en)	2001-11-29
CY2022009I2 (el)	2022-05-27
HK1078573A1 (en)	2006-03-17
KR100523501B1 (ko)	2005-10-25
NO20025227L (no)	2002-10-31
ATE407134T1 (de)	2008-09-15
EP1526134A2 (de)	2005-04-27
CN1437599A (zh)	2003-08-20
CN100355753C (zh)	2007-12-19
TNSN01077A1 (fr)	2005-11-10
NL300338I2 (nl)	2008-06-02
CR10145A (es)	2008-08-19
JP3693957B2 (ja)	2005-09-14
ES2215129T3 (es)	2004-10-01
SK286129B6 (sk)	2008-04-07
AU2001252482C1 (en)	2001-12-03
CY2022009I1 (el)	2022-05-27
EP1990341A1 (de)	2008-11-12
DE122008000011I1 (de)	2008-06-05
RS50904B (sr)	2010-08-31
NO2010007I1 (no)	2010-04-08
GEP20063799B (en)	2006-04-25
EE200200656A (et)	2004-06-15
IL152531A0 (en)	2003-05-29
JP4854970B2 (ja)	2012-01-18
UY26727A1 (es)	2001-12-28
PT1284974E (pt)	2004-06-30
OA12264A (en)	2003-11-10
BG107140A (bg)	2003-05-30
HRP20020938B1 (en)	2011-05-31
NL300338I1 (nl)	2008-05-01
HK1090836A1 (en)	2007-01-05
MY156920A (en)	2016-04-15
CZ299102B6 (cs)	2008-04-23
PL359267A1 (en)	2004-08-23
MY153023A (en)	2014-12-31
EP1990341B1 (de)	2013-01-23
CN1680371A (zh)	2005-10-12
EA200201141A1 (ru)	2003-04-24
WO2001090106A3 (en)	2002-03-28
IS6565A (is)	2002-09-24
SI1526134T1 (sl)	2008-12-31
KR20030004417A (ko)	2003-01-14
KR20050046743A (ko)	2005-05-18
PL200551B1 (pl)	2009-01-30
EA005382B1 (ru)	2005-02-24
EP1284974A2 (de)	2003-02-26
BR0110955A (pt)	2003-06-03
HUP0302474A3 (en)	2007-05-29
CN1279040C (zh)	2006-10-11
AP1965A (en)	2009-03-04
KR100548854B1 (ko)	2006-02-02
PA8517101A1 (es)	2002-10-24
BRPI0110955B8 (pt)	2021-05-25
DK1526134T3 (da)	2008-11-17
JP2003534343A (ja)	2003-11-18
AR028622A1 (es)	2003-05-14
EP1526134A3 (de)	2006-11-29
NO2020019I1 (no)	2020-06-30
BG65966B1 (bg)	2010-07-30
SI1284974T1 (en)	2004-08-31
HK1054927A1 (en)	2003-12-19
WO2001090106A2 (en)	2001-11-29
RS20090438A (en)	2010-05-07
RS51436B (en)	2011-04-30
NZ521477A (en)	2004-07-30
HRP20020938A2 (en)	2005-02-28
IS2511B (is)	2009-05-15
EA200401056A1 (ru)	2005-04-28
DE60102233T2 (de)	2005-01-27
TWI230160B (en)	2005-04-01
CA2408909C (en)	2006-06-27
EG24137A (en)	2008-08-06
EE05110B1 (et)	2008-12-15
DE60102233D1 (de)	2004-04-08
JP2005194283A (ja)	2005-07-21
DZ3464A1 (de)	2001-11-29
NO20025227D0 (no)	2002-10-31
EA007580B1 (ru)	2006-12-29

Publication	Publication Date	Title
NO327892B1 (no)	2009-10-12	Tropanderivater nyttige i terapi
US7576097B2 (en)	2009-08-18	Tropane derivatives useful in therapy
AU2001252482A1 (en)	2002-02-21	Triazolyl Tropane Derivatives as CCR5 Modulators
EA004988B1 (ru)	2004-10-28	Азабициклоалканы как модуляторы рецептора хемокинов ccr5
CN1830445B (zh)	2011-04-20	含有具有治疗作用的莨菪烷衍生物的组合物及其多晶型物

Legal Events

Date	Code	Title	Description
2010-05-03	SPCF	Filing of supplementary protection certificate	Free format text: PRODUCT NAME: MARAVIROC EVENTUELT I FORM AV ET FARMASOEYTISK AKSEPTABELT SALT; NAT. REG. NO/DATE: 07/00143-22 20071107; FIRST REG. NO/DATE: C(2007)4383-COR 20070918 Spc suppl protection certif: 2010007 Filing date: 20100408
2013-09-09	SPCG	Granted supplementary protection certificate	Free format text: PRODUCT NAME: MARAVIROC EVENTUELT I FORM AV ET FARMASOEYTISK AKSEPTABELT SALT; NAT. REG. NO/DATE: 07/00143-22 20071107; FIRST REG. NO/DATE: C(2007)4383-COR 20070918 Spc suppl protection certif: 2010007 Filing date: 20100408 Extension date: 20220920
2020-03-30	SPCS	Change of name or address of the owner of a supplementary protection certificate	Owner name: PHIVCO-1 LLC, US Spc suppl protection certif: 2010007
2020-07-13	SPCE	Application to extend a supplementary protection certificate (spc)	Free format text: PRODUCT NAME: MARAVIROC EVENTUELT I FORM AV ET FARMASOEYTISK AKSEPTABELT SALT; REG. NO/DATE: EU/1/07/418/001-010 20071107 Spc suppl protection certif: 2020019 Filing date: 20200630
2021-06-07	MK1K	Patent expired
2021-08-30	SPCG	Granted supplementary protection certificate	Free format text: PRODUCT NAME: MARAVIROC EVENTUELT I FORM AV ET FARMASOEYTISK AKSEPTABELT SALT; REG. NO/DATE: EU/1/07/418/001-010 20071107 Spc suppl protection certif: 2020019 Filing date: 20200630 Extension date: 20230320
2022-10-10	SPCX	Expiry of an spc	Spc suppl protection certif: 2010007 Expiry date: 20220920