NO313287B1 - Fremgangsmåter for fremstilling av HIV-protease inhibitorer - Google Patents
Fremgangsmåter for fremstilling av HIV-protease inhibitorer Download PDFInfo
- Publication number
- NO313287B1 NO313287B1 NO19991072A NO991072A NO313287B1 NO 313287 B1 NO313287 B1 NO 313287B1 NO 19991072 A NO19991072 A NO 19991072A NO 991072 A NO991072 A NO 991072A NO 313287 B1 NO313287 B1 NO 313287B1
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- Norway
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- group
- formula
- compound
- alkyl
- aryl
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- 238000000034 method Methods 0.000 title claims description 55
- 239000004030 hiv protease inhibitor Substances 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 132
- 125000000217 alkyl group Chemical group 0.000 claims description 91
- 125000003118 aryl group Chemical group 0.000 claims description 76
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
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- 238000006243 chemical reaction Methods 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 20
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- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 239000012296 anti-solvent Substances 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
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- 125000005842 heteroatom Chemical group 0.000 claims description 13
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- -1 hydroxybenzotriazole ester Chemical class 0.000 description 66
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- 229940125898 compound 5 Drugs 0.000 description 7
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- 229940122440 HIV protease inhibitor Drugs 0.000 description 2
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229950009390 symclosene Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- KBMBVTRWEAAZEY-UHFFFAOYSA-N trisulfane Chemical compound SSS KBMBVTRWEAAZEY-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/26—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
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/287—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70841196A | 1996-09-05 | 1996-09-05 | |
| PCT/US1997/015468 WO1998009951A2 (en) | 1996-09-05 | 1997-09-04 | Intermediates for making hiv-protease inhibitors and methods of making hiv-protease inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO991072L NO991072L (no) | 1999-03-04 |
| NO991072D0 NO991072D0 (no) | 1999-03-04 |
| NO313287B1 true NO313287B1 (no) | 2002-09-09 |
Family
ID=24845703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19991072A NO313287B1 (no) | 1996-09-05 | 1999-03-04 | Fremgangsmåter for fremstilling av HIV-protease inhibitorer |
Country Status (33)
| Country | Link |
|---|---|
| EP (2) | EP0927165B1 (xx) |
| JP (3) | JP4149000B2 (xx) |
| KR (1) | KR100563289B1 (xx) |
| CN (2) | CN1183117C (xx) |
| AP (2) | AP2003002938A0 (xx) |
| AT (2) | ATE254603T1 (xx) |
| AU (2) | AU740369B2 (xx) |
| BG (2) | BG64793B1 (xx) |
| BR (1) | BR9713192A (xx) |
| CA (1) | CA2264756A1 (xx) |
| CZ (2) | CZ298175B6 (xx) |
| DE (2) | DE69734689T2 (xx) |
| DK (2) | DK1361216T3 (xx) |
| EA (1) | EA002051B1 (xx) |
| EE (1) | EE04465B1 (xx) |
| ES (2) | ES2210573T3 (xx) |
| GE (1) | GEP20022799B (xx) |
| HK (1) | HK1062171A1 (xx) |
| HU (1) | HUP0000028A3 (xx) |
| IL (1) | IL128567A (xx) |
| IS (1) | IS2030B (xx) |
| NO (1) | NO313287B1 (xx) |
| NZ (1) | NZ334909A (xx) |
| OA (1) | OA10988A (xx) |
| PL (2) | PL198408B1 (xx) |
| PT (1) | PT927165E (xx) |
| SG (1) | SG94780A1 (xx) |
| SI (2) | SI1361216T1 (xx) |
| SK (2) | SK284899B6 (xx) |
| TR (1) | TR199900473T2 (xx) |
| UA (1) | UA67727C2 (xx) |
| WO (1) | WO1998009951A2 (xx) |
| YU (1) | YU11599A (xx) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0641038A (ja) * | 1992-07-17 | 1994-02-15 | Mitsubishi Kasei Corp | カルボン酸誘導体 |
| US5484926A (en) * | 1993-10-07 | 1996-01-16 | Agouron Pharmaceuticals, Inc. | HIV protease inhibitors |
| JPH07248183A (ja) * | 1994-03-11 | 1995-09-26 | Osaka Gas Co Ltd | 浴室兼用衣類乾燥室 |
| JP3298293B2 (ja) * | 1994-03-14 | 2002-07-02 | 松下電器産業株式会社 | 厨芥処理機 |
| WO1996028423A1 (fr) * | 1995-03-15 | 1996-09-19 | Sankyo Company, Limited | Composes dipeptidiques de structure ahpba |
| AU717637B2 (en) * | 1995-09-26 | 2000-03-30 | Agouron Pharmaceuticals, Inc. | Production of amide derivatives and intermediates therefor |
| WO1997011938A1 (fr) * | 1995-09-26 | 1997-04-03 | Japan Tobacco Inc. | Procede de production de derives amides et de leurs intermediaires |
| US5962704A (en) * | 1995-09-26 | 1999-10-05 | Japan Tobacco Inc. | Production of amide derivatives and intermediate compounds therefor |
| US5925767A (en) * | 1996-02-24 | 1999-07-20 | Basf Aktiengesellschaft | Pyrazole-4-yl-hetaroyl derivatives as herbicides |
-
1997
- 1997-04-09 UA UA99041906A patent/UA67727C2/uk unknown
- 1997-09-04 EP EP97941402A patent/EP0927165B1/en not_active Expired - Lifetime
- 1997-09-04 CN CNB971984484A patent/CN1183117C/zh not_active Expired - Fee Related
- 1997-09-04 SI SI9730719T patent/SI1361216T1/sl unknown
- 1997-09-04 KR KR1019997001902A patent/KR100563289B1/ko not_active IP Right Cessation
- 1997-09-04 CZ CZ20070084A patent/CZ298175B6/cs not_active IP Right Cessation
- 1997-09-04 SK SK282-99A patent/SK284899B6/sk not_active IP Right Cessation
- 1997-09-04 ES ES97941402T patent/ES2210573T3/es not_active Expired - Lifetime
- 1997-09-04 DK DK03013275T patent/DK1361216T3/da active
- 1997-09-04 SK SK90-2005A patent/SK285278B6/sk not_active IP Right Cessation
- 1997-09-04 AP APAP/P/2003/002938A patent/AP2003002938A0/en unknown
- 1997-09-04 SI SI9730605T patent/SI0927165T1/xx unknown
- 1997-09-04 AT AT97941402T patent/ATE254603T1/de not_active IP Right Cessation
- 1997-09-04 EE EEP199900109A patent/EE04465B1/xx not_active IP Right Cessation
- 1997-09-04 PL PL331801A patent/PL198408B1/pl not_active IP Right Cessation
- 1997-09-04 CN CNB2004100073691A patent/CN1305854C/zh not_active Expired - Fee Related
- 1997-09-04 YU YU11599A patent/YU11599A/sh unknown
- 1997-09-04 BR BR9713192-0A patent/BR9713192A/pt not_active Application Discontinuation
- 1997-09-04 WO PCT/US1997/015468 patent/WO1998009951A2/en active IP Right Grant
- 1997-09-04 PL PL381445A patent/PL201758B1/pl not_active IP Right Cessation
- 1997-09-04 NZ NZ334909A patent/NZ334909A/en unknown
- 1997-09-04 DK DK97941402T patent/DK0927165T3/da active
- 1997-09-04 SG SG200101308A patent/SG94780A1/en unknown
- 1997-09-04 PT PT97941402T patent/PT927165E/pt unknown
- 1997-09-04 TR TR1999/00473T patent/TR199900473T2/xx unknown
- 1997-09-04 EP EP03013275A patent/EP1361216B1/en not_active Expired - Lifetime
- 1997-09-04 ES ES03013275T patent/ES2252586T3/es not_active Expired - Lifetime
- 1997-09-04 DE DE69734689T patent/DE69734689T2/de not_active Expired - Fee Related
- 1997-09-04 HU HU0000028A patent/HUP0000028A3/hu unknown
- 1997-09-04 CZ CZ0071699A patent/CZ298174B6/cs not_active IP Right Cessation
- 1997-09-04 AT AT03013275T patent/ATE309990T1/de not_active IP Right Cessation
- 1997-09-04 CA CA002264756A patent/CA2264756A1/en not_active Abandoned
- 1997-09-04 JP JP51283198A patent/JP4149000B2/ja not_active Expired - Fee Related
- 1997-09-04 AU AU43317/97A patent/AU740369B2/en not_active Ceased
- 1997-09-04 DE DE69726298T patent/DE69726298T2/de not_active Expired - Fee Related
- 1997-09-04 AP APAP/P/1999/001497A patent/AP1322A/en active
- 1997-09-04 IL IL12856797A patent/IL128567A/en not_active IP Right Cessation
- 1997-09-04 EA EA199900257A patent/EA002051B1/ru not_active IP Right Cessation
- 1997-09-04 GE GEAP19974736A patent/GEP20022799B/en unknown
-
1999
- 1999-02-19 IS IS4982A patent/IS2030B/is unknown
- 1999-03-03 OA OA9900049A patent/OA10988A/en unknown
- 1999-03-04 NO NO19991072A patent/NO313287B1/no not_active IP Right Cessation
- 1999-04-02 BG BG103305A patent/BG64793B1/bg unknown
-
2002
- 2002-01-31 AU AU14736/02A patent/AU766155B2/en not_active Ceased
-
2004
- 2004-05-12 HK HK04103309A patent/HK1062171A1/xx not_active IP Right Cessation
-
2006
- 2006-01-18 BG BG109411A patent/BG65237B1/bg unknown
-
2007
- 2007-10-29 JP JP2007280974A patent/JP2008056693A/ja not_active Withdrawn
- 2007-10-29 JP JP2007280975A patent/JP2008088178A/ja active Pending
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Legal Events
| Date | Code | Title | Description |
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| MM1K | Lapsed by not paying the annual fees |