OA10864A - Compounds useful for the inhibition of the replication of hiv-1 and hiv-1 mutants - Google Patents

Compounds useful for the inhibition of the replication of hiv-1 and hiv-1 mutants Download PDF

Info

Publication number: OA10864A
Authority: OA; OAPI
Prior art keywords: hiv; methyl; compound; compounds; reaction mixture
Prior art date: 1995-11-30

Application number

OA9800070A

Other languages

English (en)

Inventor

Walter Gerhard Brouwer

Ewa Maria Osika

Benjamin James Pierce

Original Assignee

Uniroyal Chem Co Inc

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.)

1995-11-30

Filing date

1998-05-29

Publication date

2003-02-18

1998-05-29 Application filed by Uniroyal Chem Co Inc filed Critical Uniroyal Chem Co Inc

2003-02-18 Publication of OA10864A publication Critical patent/OA10864A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 51
230000005764 inhibitory process Effects 0.000 title abstract description 3
230000010076 replication Effects 0.000 title abstract description 3
241000713772 Human immunodeficiency virus 1 Species 0.000 claims abstract description 23
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 16
208000015181 infectious disease Diseases 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
241000720945 Hosta Species 0.000 claims 3
239000008194 pharmaceutical composition Substances 0.000 claims 3
102100034343 Integrase Human genes 0.000 abstract description 21
108010092799 RNA-directed DNA polymerase Proteins 0.000 abstract description 21
208000030507 AIDS Diseases 0.000 abstract description 5
238000000338 in vitro Methods 0.000 abstract description 2
238000001727 in vivo Methods 0.000 abstract description 2
238000011321 prophylaxis Methods 0.000 abstract description 2
208000011580 syndromic disease Diseases 0.000 abstract description 2
230000001225 therapeutic effect Effects 0.000 abstract description 2
201000010099 disease Diseases 0.000 abstract 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
-1 ester compounds Chemical class 0.000 description 43
239000011541 reaction mixture Substances 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
239000007787 solid Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
239000000243 solution Substances 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
230000000840 anti-viral effect Effects 0.000 description 8
230000000052 comparative effect Effects 0.000 description 8
239000002904 solvent Substances 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229960000443 hydrochloric acid Drugs 0.000 description 6
235000011167 hydrochloric acid Nutrition 0.000 description 6
NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
241000700605 Viruses Species 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000004113 cell culture Methods 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
229960001407 sodium bicarbonate Drugs 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
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235000019439 ethyl acetate Nutrition 0.000 description 4
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 4
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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AFFZVBHMMXZNKE-UHFFFAOYSA-N 2-methylfuran-3-carbonyl chloride Chemical compound CC=1OC=CC=1C(Cl)=O AFFZVBHMMXZNKE-UHFFFAOYSA-N 0.000 description 3
DFTNCGRDYHINDS-UHFFFAOYSA-N 3-bromo-2-methylthiophene Chemical compound CC=1SC=CC=1Br DFTNCGRDYHINDS-UHFFFAOYSA-N 0.000 description 3
KEXOQPIZCSACLO-UHFFFAOYSA-N 4-chloro-3-(3-methylbut-2-enoxy)aniline Chemical compound CC(C)=CCOC1=CC(N)=CC=C1Cl KEXOQPIZCSACLO-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
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238000001704 evaporation Methods 0.000 description 3
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229960000689 nevirapine Drugs 0.000 description 3
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
HDMHBHNRWDNNCD-UHFFFAOYSA-N 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)thymine Chemical compound OCCOCN1C(=O)NC(=O)C(C)=C1SC1=CC=CC=C1 HDMHBHNRWDNNCD-UHFFFAOYSA-N 0.000 description 2
LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 2
BUMGQSCPTLELLS-UHFFFAOYSA-N 2-chloro-5-nitrophenol Chemical compound OC1=CC([N+]([O-])=O)=CC=C1Cl BUMGQSCPTLELLS-UHFFFAOYSA-N 0.000 description 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
CFGQZVOVFIZRMN-UHFFFAOYSA-N 2-methylfuran-3-carboxylic acid Chemical compound CC=1OC=CC=1C(O)=O CFGQZVOVFIZRMN-UHFFFAOYSA-N 0.000 description 2
OGAJGUIMFMRGRB-UHFFFAOYSA-N 3,5-dibromo-2-methylthiophene Chemical compound CC=1SC(Br)=CC=1Br OGAJGUIMFMRGRB-UHFFFAOYSA-N 0.000 description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
RCSLUNOLLUVOOG-NSHDSACASA-N 4-chloro-8-methyl-7-(3-methyl-but-2-enyl)-6,7,8,9-tetrahydro-2h-2,7,9a-triaza-benzo[cd]azulene-1-thione Chemical compound C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC(Cl)=CC1=C32 RCSLUNOLLUVOOG-NSHDSACASA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
235000008529 Ziziphus vulgaris Nutrition 0.000 description 2
244000126002 Ziziphus vulgaris Species 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229940125890 compound Ia Drugs 0.000 description 2
239000000824 cytostatic agent Substances 0.000 description 2
230000001085 cytostatic effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
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CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
WTTIBCHOELPGFK-LBPRGKRZSA-N r82150 Chemical compound C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC=CC1=C32 WTTIBCHOELPGFK-LBPRGKRZSA-N 0.000 description 2
239000002516 radical scavenger Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000017960 syncytium formation Effects 0.000 description 2
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ASOMNDIOOKDVDC-UHFFFAOYSA-N 1h-indol-2-yl-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl]methanone Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=CC=C3C=2)CC1 ASOMNDIOOKDVDC-UHFFFAOYSA-N 0.000 description 1
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CRZJPEIBPQWDGJ-UHFFFAOYSA-N 2-chloro-1,1-dimethoxyethane Chemical compound COC(CCl)OC CRZJPEIBPQWDGJ-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
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125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
YZHIXLCGPOTQNB-UHFFFAOYSA-N 2-methyl-furan-3-carbothioic acid [4-chloro-3-(3-methyl-but-2-enyloxy)-phenyl]-amide Chemical compound C1=C(Cl)C(OCC=C(C)C)=CC(NC(=S)C2=C(OC=C2)C)=C1 YZHIXLCGPOTQNB-UHFFFAOYSA-N 0.000 description 1
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125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
UVRZFSXLZABFGH-UHFFFAOYSA-N 3,5-dibromo-3-methyl-2h-thiophene Chemical compound CC1(Br)CSC(Br)=C1 UVRZFSXLZABFGH-UHFFFAOYSA-N 0.000 description 1
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101150065749 Churc1 gene Proteins 0.000 description 1
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208000031886 HIV Infections Diseases 0.000 description 1
241000725303 Human immunodeficiency virus Species 0.000 description 1
101900297506 Human immunodeficiency virus type 1 group M subtype B Reverse transcriptase/ribonuclease H Proteins 0.000 description 1
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IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
150000001721 carbon Chemical class 0.000 description 1
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239000000969 carrier Substances 0.000 description 1
239000003518 caustics Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000012228 culture supernatant Substances 0.000 description 1
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230000035772 mutation Effects 0.000 description 1
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230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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238000001228 spectrum Methods 0.000 description 1
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JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Virology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
AIDS & HIV (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Furan Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

OA9800070A 1995-11-30 1998-05-29 Compounds useful for the inhibition of the replication of hiv-1 and hiv-1 mutants OA10864A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/565,493 US5696151A (en)	1995-11-30	1995-11-30	Compounds useful for the inhibition of the replication of HIV-1 and HIV-1 mutants

Publications (1)

Publication Number	Publication Date
OA10864A true OA10864A (en)	2003-02-18

Family

ID=24258853

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9800070A OA10864A (en)	1995-11-30	1998-05-29	Compounds useful for the inhibition of the replication of hiv-1 and hiv-1 mutants

Country Status (20)

Country	Link
US (1)	US5696151A (de)
EP (1)	EP0874839B1 (de)
JP (1)	JP3027771B2 (de)
KR (1)	KR100505841B1 (de)
CN (1)	CN1098847C (de)
AP (1)	AP902A (de)
AT (1)	ATE224382T1 (de)
AU (1)	AU704086B2 (de)
BR (1)	BR9611838A (de)
CA (1)	CA2237194C (de)
DE (1)	DE69623819T2 (de)
DK (1)	DK0874839T3 (de)
ES (1)	ES2183986T3 (de)
HU (1)	HU223660B1 (de)
NZ (1)	NZ324118A (de)
OA (1)	OA10864A (de)
PT (1)	PT874839E (de)
TW (1)	TW448169B (de)
WO (1)	WO1997019940A1 (de)
ZA (1)	ZA969490B (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6143780A (en) *	1999-09-17	2000-11-07	Uniroyal Chemical Company, Inc.	N-arylmethylthioanilide compounds useful for the inhibition of the replication of HIV
US6017947A (en) *	1999-09-17	2000-01-25	Brouwer; Walter Gerhard	Heterocyclic carbodithioperoxyimidic compounds useful for the inhibition of the replication of HIV
US6498254B1 (en) *	2001-10-29	2002-12-24	Uniroyal Chemical Company, Inc.	Antiretroviral compounds and compositions
US7064139B2 (en) *	2001-10-29	2006-06-20	Uniroyal Chemical Company, Inc.	Method for treating retroviral infections
DE102008015033A1 (de)	2008-03-17	2009-09-24	Aicuris Gmbh & Co. Kg	Substituierte (Pyrazolyl-carbonyl)imidazolidinone und ihre Verwendung
DE102008015032A1 (de)	2008-03-17	2009-09-24	Aicuris Gmbh & Co. Kg	Substituierte Pyrazolamide und ihre Verwendung
DE102008062878A1 (de) *	2008-12-17	2010-06-24	Aicuris Gmbh & Co. Kg	Substituierte Furancarboxamide und ihre Verwendung
DE102008062863A1 (de)	2008-12-17	2010-06-24	Aicuris Gmbh & Co. Kg	Substituierte (Thiophenyl-carbonyl)imidazolidinone und ihre Verwendung
CN101987842A (zh) *	2009-07-31	2011-03-23	上海开拓者医药发展有限公司	一种2-甲基噻吩衍生物的制备方法
WO2016012424A1 (en) *	2014-07-24	2016-01-28	Bayer Cropscience Aktiengesellschaft	Fungicidal pyrazole derivatives

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5268389A (en) *	1989-10-16	1993-12-07	Uniroyal Chemical Company, Inc.	Thiocarboxylate ester compounds compositions containing the same
US5968910A (en) *	1994-11-30	1999-10-19	Jan M. R. Balzarini	Compositions containing two or three inhibitors of different HIV reverse transcriptases

1995
- 1995-11-30 US US08/565,493 patent/US5696151A/en not_active Expired - Lifetime
1996
- 1996-11-08 TW TW085113662A patent/TW448169B/zh not_active IP Right Cessation
- 1996-11-12 ZA ZA969490A patent/ZA969490B/xx unknown
- 1996-11-15 CA CA002237194A patent/CA2237194C/en not_active Expired - Lifetime
- 1996-11-15 AU AU11199/97A patent/AU704086B2/en not_active Expired
- 1996-11-15 AP APAP/P/1998/001245A patent/AP902A/en active
- 1996-11-15 NZ NZ324118A patent/NZ324118A/xx not_active IP Right Cessation
- 1996-11-15 AT AT96942010T patent/ATE224382T1/de active
- 1996-11-15 BR BR9611838A patent/BR9611838A/pt active Search and Examination
- 1996-11-15 PT PT96942010T patent/PT874839E/pt unknown
- 1996-11-15 EP EP96942010A patent/EP0874839B1/de not_active Expired - Lifetime
- 1996-11-15 HU HU9901990A patent/HU223660B1/hu active IP Right Grant
- 1996-11-15 ES ES96942010T patent/ES2183986T3/es not_active Expired - Lifetime
- 1996-11-15 KR KR10-1998-0703958A patent/KR100505841B1/ko not_active Expired - Lifetime
- 1996-11-15 CN CN96198705A patent/CN1098847C/zh not_active Expired - Lifetime
- 1996-11-15 WO PCT/US1996/018394 patent/WO1997019940A1/en not_active Ceased
- 1996-11-15 DK DK96942010T patent/DK0874839T3/da active
- 1996-11-15 DE DE69623819T patent/DE69623819T2/de not_active Expired - Lifetime
- 1996-11-15 JP JP9520533A patent/JP3027771B2/ja not_active Expired - Lifetime
1998
- 1998-05-29 OA OA9800070A patent/OA10864A/en unknown

Also Published As

Publication number	Publication date
DE69623819T2 (de)	2003-05-28
CN1203596A (zh)	1998-12-30
AU1119997A (en)	1997-06-19
ZA969490B (en)	1997-06-02
EP0874839A1 (de)	1998-11-04
HUP9901990A2 (en)	2000-07-28
DE69623819D1 (de)	2002-10-24
AP902A (en)	2000-11-23
KR19990071682A (ko)	1999-09-27
HUP9901990A3 (en)	2000-08-28
CN1098847C (zh)	2003-01-15
CA2237194C (en)	2006-06-13
HU223660B1 (hu)	2004-11-29
US5696151A (en)	1997-12-09
AP9801245A0 (en)	1998-06-30
BR9611838A (pt)	1999-03-09
CA2237194A1 (en)	1997-06-05
NZ324118A (en)	1999-02-25
ES2183986T3 (es)	2003-04-01
EP0874839B1 (de)	2002-09-18
JPH11504657A (ja)	1999-04-27
WO1997019940A1 (en)	1997-06-05
DK0874839T3 (da)	2003-01-27
TW448169B (en)	2001-08-01
AU704086B2 (en)	1999-04-15
PT874839E (pt)	2003-02-28
ATE224382T1 (de)	2002-10-15
JP3027771B2 (ja)	2000-04-04
KR100505841B1 (ko)	2005-12-14
HK1016601A1 (en)	1999-11-05

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