WO1998009951B1 - Intermediates for making hiv-protease inhibitors and methods of making hiv-protease inhibitors - Google Patents
Intermediates for making hiv-protease inhibitors and methods of making hiv-protease inhibitorsInfo
- Publication number
- WO1998009951B1 WO1998009951B1 PCT/US1997/015468 US9715468W WO9809951B1 WO 1998009951 B1 WO1998009951 B1 WO 1998009951B1 US 9715468 W US9715468 W US 9715468W WO 9809951 B1 WO9809951 B1 WO 9809951B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- formula
- compound
- aryl
- alkyl
- Prior art date
Links
Abstract
HIV-protease inhibitors inhibit or block the biological activity of the HIV-protease enzyme, causing the replication of the HIV virus to terminate. These compounds can be prepared by the novel methods of the present invention using the novel inventive compounds and intermediates of formula (3). R1 and X are defined in the claims
Claims
1. A compound of formula 3:
wherein R, is heteroaryl; or a group of formula 8
wherein each R3 is independently an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; or further wherein R1 is a group of formula 10.
R40
^
R5 -R5
wherein R4 and each R5 independently are an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; and
X is OH; OR7, wherein R7 is alkyl or aryl; halogen; pseudohalogen; OSO2R8, wherein R8 is alkyi or aryl; heteroaryl bonded through the heteroatom; or
- -
N-hydroxyheterocyclic bonded through the-oxygen, with the proviso that when R^ is CH3C(O)-, X cannot be -OH; or a pharmaceutically acceptable salt or solvate thereof.
2. A compound according to claim 1 , wherein R1 is -C(O)CH3.
3. A compound according to claim 2, wherein X is Cl.
4. A compound according to claim 1 , wherein X is Cl.
5. A compound of formula 2:
wherein R1 is a heteroaryl group; or a group of formula 8
wherein R2 is a C2 to C8 alkyl group, a cycloalkyl group, a heterocycloaikyl group, or O-R6, wherein R6 is an alkyl group, an aralkyl group, or an aryl group; or further wherein R1 is a group of formula 9
wherein each R3 independently is an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; or further wherein R1 is a group of formula 10
-67-
RR0 ^ R«
wherein R4 and each R5 independently are an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; or a pharmaceutically acceptable salt or solvate thereof.
6. A method of making a compound of formula 2:
comprising: adding under sufficient conditions a suitable protecting group R, to a compound of formula 1
wherein R., is a heteroaryl group; or a group of formula 8
wherein R2 is a C2 to C8 alkyl group, a cycloalkyl group, a heterocycloaikyl group, or O-R6, wherein R6 is an alkyl group, an aralkyl group, or an aryl group; ■ or further wherein R1 is a group of formula 9
wherein each R3 is independently an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; or further wherein R^ is a group of formula 10
R40.
^
wherein R4 and each R5 independently are an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; to form the compound of formula 2.
7. A method of making a compound of formula 3
comprising: adding under sufficient conditions a suitable protecting group R and a leaving group X to a compound of formula 1
wherein R1 is heteroaryl; or a group of formula 8
0
R.
wherein R2 is an alkyl group, a cycloalkyl group, a heterocycloaikyl group, or O-R6, wherein R6 is an alkyl group, an aralkyl group, or an aryl group;
- -
or further wherein R^ is a group of formula 9
wherein each R3 is independently an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; or further wherein R., is a group of formula 10
R40. R ^
wherein R4 and each R5 independently are an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; and
X is OH; OR7, wherein R7 is alkyl or aryl; halogen; pseudohalogen; OSO2R8, wherein R8 is alkyl or aryl; heteroaryl bonded through the heteroatom; or N-hydroxyheterocyclic bonded through the oxygen, with the proviso that when R1 is CH3C(O)- , X cannot be -OH; to form the compound of formula 3.
8. A method according to claim 7, wherein R, is -C(O)CH3.
9. A method according to claim 7, wherein X is Cl.
10. A method according to claim 9, wherein R1 is -C(O)CH3.
11. A method of making a compound of formula 3
wherein R^ is heteroaryl; or a group of formula 8
0
R,
wherein R2 is an alkyl group, a cycloalkyl group, a heterocycloaikyl group, or O-R6, wherein R6 is an alkyl group, an aralkyl group, or an aryl group; or further wherein R is a group of formula 9
wherein each R3 is independently an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; or further wherein R., is a group of formula 10
RΛ
R ^, ϊ C
- *
wherein R4 and each R5 independently are an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; and
X is OH; OR7, wherein R7 is alkyl or aryl; halogen; pseudohalogen; OSO2R8, wherein R8 is alkyi or aryl; heteroaryl bonded through the heteroatom; or N-hydroxyheterocyclic bonded through the oxygen, with the proviso that when R., is CH3C(0)-, X cannot be -OH;
to form the compound of formula 3.
12. A method according to claim 11 , wherein X is Cl.
13. A method of making a compound of formula 4
comprising: converting under sufficient conditions a compound of formula 3
wherein R1 is heteroaryl; or a group of formula 8
O
R.
wherein R2 is an alkyl group, a cycloalkyl group, a heterocycloaikyl group, or O-R6 wherein R6 is an alkyl group, an aralkyl group, or an aryl group;
- -
or further wherein R^ is a group of formula 9
wherein each R3 independently is an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; or further wherein R1 is a group of formula 10
RR0 ^ R-.
wherein R4 and each R5 independently are an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; and
X is OH; OR7, wherein R7 is alkyl or aryl; halogen; pseudohalogen; OSO2R8, wherein R8 is alkyl or aryl; heteroaryl bonded through the heteroatom; or N-hydroxyheterocyclic bonded through the oxygen, to the compound of formula 4.
14. A method according to claim 13, wherein R., is -C(0)CH3.
15. A method according to claim 13, wherein X is Cl.
16. A method according to claim 15, wherein R1 is -C(0)CH3.
17. A method of making a compound of 'formula 4
-73-
comprising: deprotecting a compound of formula 5
and adding to the deprotected compound of formula 5, under sufficient conditions, a compound of formula 3:
wherein R1 is heteroaryl; or a group of formula 8
wherein R2 is an alkyl group, a cycloalkyl group, a heterocycloaikyl group, or O-R6, wherein R6 is an alkyl group, an aralkyl group, or an aryl group; or further wherein R1 is a group of formula 9
wherein each R3 independently is an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; or further wherein R1 is a group of formula 10
R40. R, ^
Rfi
wherein R4 and each R5 independently are an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; and
X is OH; OR7, wherein R7 is alkyl or aryl; halogen; pseudohalogen; OSO2R8, wherein R8 is alkyl or aryl; heteroaryl bonded through the heteroatom; or N-hydroxyheterocyclic bonded through the oxygen, to form the compound of formula 4.
18. A method according to claim 17, wherein R^ is -C(O)CH3.
19. A method according to claim 17, wherein X is Cl.
20. A method according to claim 19, wherein R1 is -C(O)CH3.
21. A method of making a compound of formula 4
comprising: combining under sufficient conditions a compound of formula 3:
wherein R2 is an alkyl group, a cycloalkyl group, a heterocycloaikyl group, or O-R6, wherein R6 is an alkyl group, an aralkyl group, or an aryl group; or further wherein R1 is a group of formula 9
wherein R4 and each R5 independently are an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; and
X is OH; OR7, wherein R7 is alkyl or aryl; halogen; pseudohalogen; OSO2R8 wherein R8 is alkyl or aryl; heteroaryl bonded through the heteroatom; or N-hydroxyheterocyclic bonded through the oxygen, with a compound of formula 6
to obtain the compound of formula 4.
- -
22. A method according to claim 21 , wherein R^ is -C(O)CH3.
23. A method according to claim 21 , wherein X is Cl.
24. A method according to claim 23, wherein R is -C(O)CH3.
25. A method of making a compound of formula 7
comprising: converting under sufficient conditions a compound of formula 4
(a) contacting the compound of formula 4 with an organic solvent;
(b) contacting the compound of formula 4 with methanesulfonic acid under conditions sufficient to form a compound of formula 7; and
(c) spray drying the compound of formula 7.
26. A method according to claim 25, wherein the organic solvent is ethanol.
- -
27. A method of making a compound of formula 7
comprising: converting under sufficient conditions a compound of formula 4
to the compound of formula 7 by:
(a) combining the compound of formula 4, a suitable solvent, and methanesulfonic acid to form the compound of formula 7, the compound of formula 7 being dissolved in solution;
(b) adding a first antisolvent to the solution containing the compound of formula 7;
(c) agitating the compound of formula 7 and the first antisolvent to form a product having a solid phase and a liquid phase; and
(d) filtering and washing the product with a second antisolvent, the second antisolvent being the same as or different from the first antisolvent, to obtain a solid.
28. A method according to claim 27, the method additionally comprising:
(e) drying the solid.
29. A method according to claim 27, wherein the suitable solvent is tetrahydrofuran.
30. A method according to claim 27, wherein the first antisolvent is diethyl ether.
31. A method of making a compound of formula 4
comprising: converting under sufficient conditions a compound of formula 2
wherein R is heteroaryl; or a group of formula 8
wherein each R3 independently is an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; or further wherein R is a group of formula 10
R40. R.
*R«
wherein R4 and each R5 independently are an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; to the compound of formula 4.
32. A method according to claim 31 , wherein R is -C(O)CH3.
33. A method of making a compound of formula 7
comprising: deprotecting a compound of formula 5
adding to the deprotected compound of formula 5, under sufficient conditions, a compound of formula 3:
wherein R1 is heteroaryl; or a group of formula 8
wherein R2 is an alkyl group, a cycloalkyl group, a heterocycloaikyl group, or O-R6, wherein R6 is an alkyl group, an aralkyl group, or an aryl group; or further wherein R1 is a group of formula 9
wherein each R3 independently is an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; or further wherein R., is a group of formula 10
wherein R4 and each R5 independently are an alkyl group, a cycloalkyl group, a heterocycloaikyl group, an aryl group, or a heteroaryl group; and
X is OH; OR7, wherein R7 is alkyl or aryl; halogen; pseudohalogen; OSO2R8, wherein R8 is alkyl or aryl; heteroaryl bonded through the heteroatom; or N-hydroxyheterocyclic bonded through the oxygen, to form a compound of formula 4:
and converting the compound of formula 4 to the compound of formula 7.
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| UA99041906A UA67727C2 (en) | 1996-09-05 | 1997-04-09 | Intermediate compounds for preparation of hiv-protease inhibitors and methods for the preparation of hiv-protease inhibitors |
| EP97941402A EP0927165B1 (en) | 1996-09-05 | 1997-09-04 | Intermediates for making hiv-protease inhibitors and methods of making hiv-protease inhibitors |
| EA199900257A EA002051B1 (en) | 1996-09-05 | 1997-09-04 | Methods of making hiv-protease inhibitors |
| SK282-99A SK284899B6 (en) | 1996-09-05 | 1997-09-04 | Intermediates for preparing HIV-protease inhibitors and process for preparing the HIV-protease inhibitors |
| IL12856797A IL128567A (en) | 1996-09-05 | 1997-09-04 | Intermediates for preparing hiv-protease inhibitor nelfinavir, process for their preparation and methods of preparing nelfinavir |
| AU43317/97A AU740369B2 (en) | 1995-09-26 | 1997-09-04 | Intermediates for making HIV-protease inhibitors and methods of making HIV-protease inhibitors |
| DK97941402T DK0927165T3 (en) | 1996-09-05 | 1997-09-04 | Intermediates for the preparation of HIV protease inhibitors and method for producing HIV protease inhibitors |
| SI9730719T SI1361216T1 (en) | 1996-09-05 | 1997-09-04 | Method of making a HIV-Protease inhibitor |
| DE69726298T DE69726298T2 (en) | 1996-09-05 | 1997-09-04 | INTERMEDIATE PRODUCTS FOR THE PRODUCTION OF HIV PROTEASE INHIBITORS AND METHOD FOR THE PRODUCTION OF HIV PROTEASE INHIBITORS |
| JP51283198A JP4149000B2 (en) | 1996-09-05 | 1997-09-04 | Intermediate for producing HIV-protease inhibitor and method for producing HIV-protease inhibitor |
| SI9730605T SI0927165T1 (en) | 1996-09-05 | 1997-09-04 | Intermediates for making hiv-protease inhibitors and methods of making hiv-protease inhibitors |
| AT97941402T ATE254603T1 (en) | 1996-09-05 | 1997-09-04 | INTERMEDIATE PRODUCTS FOR PRODUCING HIV PROTEASE INHIBITORS AND METHOD FOR PRODUCING HIV PROTEASE INHIBITORS |
| NZ334909A NZ334909A (en) | 1996-09-05 | 1997-09-04 | Intermediates for making HIV protease inhibitors |
| CA002264756A CA2264756A1 (en) | 1996-09-05 | 1997-09-04 | Intermediates for making hiv-protease inhibitors and methods of making hiv-protease inhibitors |
| BR9713192-0A BR9713192A (en) | 1996-09-05 | 1997-09-04 | Intermediates for making HIV protease inhibitors and methods of making HIV protease inhibitors |
| SK90-2005A SK285278B6 (en) | 1996-09-05 | 1997-09-04 | Method of making HIV-Protease inhibitor |
| APAP/P/1999/001497A AP1322A (en) | 1996-09-05 | 1997-09-04 | Intermediates for making HIV- protease inhibitors and methods of making HIV protease inhibitors. |
| APAP/P/2003/002938A AP2003002938A0 (en) | 1996-09-05 | 1997-09-04 | Intermediates for making HIV- protease inhibitors and methods of making HIV protease inhibitors. |
| PL331801A PL198408B1 (en) | 1996-09-05 | 1997-09-04 | Intermediate compounds for use in production of hiv protease inhibitors and method of obtaining such inhibitors |
| EEP199900109A EE04465B1 (en) | 1996-09-05 | 1997-09-04 | Intermediates for the preparation of HIV protease inhibitors and methods for the preparation of HIV protease inhibitors |
| IS4982A IS2030B (en) | 1996-09-05 | 1999-02-19 | Intermediates for the construction of HIV protease inhibitors and methods for the construction of HIV protease inhibitors |
| NO19991072A NO313287B1 (en) | 1996-09-05 | 1999-03-04 | Methods for Preparing HIV Protease Inhibitors |
| BG103305A BG64793B1 (en) | 1996-09-05 | 1999-04-02 | Intermediate compounds for the preparation of hiv protease inhibitors and methods for the preparation of hiv protease inhibitors |
| AU14736/02A AU766155B2 (en) | 1995-09-26 | 2002-01-31 | Intermediates for making HIV-protease inhibitors and methods of making HIV-protease inhibitors |
| JP2007280974A JP2008056693A (en) | 1996-09-05 | 2007-10-29 | Intermediate for production of hiv-protease inhibitor, and method for producing hiv-protease inhibitor |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70841196A | 1996-09-05 | 1996-09-05 | |
| US08/708,411 | 1996-09-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO1998009951A2 WO1998009951A2 (en) | 1998-03-12 |
| WO1998009951A3 WO1998009951A3 (en) | 1998-07-09 |
| WO1998009951B1 true WO1998009951B1 (en) | 1998-08-13 |
Family
ID=24845703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1997/015468 WO1998009951A2 (en) | 1995-09-26 | 1997-09-04 | Intermediates for making hiv-protease inhibitors and methods of making hiv-protease inhibitors |
Country Status (32)
| Country | Link |
|---|---|
| EP (2) | EP1361216B1 (en) |
| JP (3) | JP4149000B2 (en) |
| KR (1) | KR100563289B1 (en) |
| CN (2) | CN1305854C (en) |
| AP (2) | AP1322A (en) |
| AT (2) | ATE309990T1 (en) |
| AU (2) | AU740369B2 (en) |
| BG (2) | BG64793B1 (en) |
| BR (1) | BR9713192A (en) |
| CA (1) | CA2264756A1 (en) |
| CZ (2) | CZ298175B6 (en) |
| DE (2) | DE69734689T2 (en) |
| DK (2) | DK1361216T3 (en) |
| EA (1) | EA002051B1 (en) |
| EE (1) | EE04465B1 (en) |
| ES (2) | ES2252586T3 (en) |
| GE (1) | GEP20022799B (en) |
| HU (1) | HUP0000028A3 (en) |
| IL (1) | IL128567A (en) |
| IS (1) | IS2030B (en) |
| NO (1) | NO313287B1 (en) |
| NZ (1) | NZ334909A (en) |
| OA (1) | OA10988A (en) |
| PL (2) | PL198408B1 (en) |
| PT (1) | PT927165E (en) |
| SG (1) | SG94780A1 (en) |
| SI (2) | SI1361216T1 (en) |
| SK (2) | SK285278B6 (en) |
| TR (1) | TR199900473T2 (en) |
| UA (1) | UA67727C2 (en) |
| WO (1) | WO1998009951A2 (en) |
| YU (1) | YU11599A (en) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0641038A (en) * | 1992-07-17 | 1994-02-15 | Mitsubishi Kasei Corp | Carboxylic acid derivative |
| US5484926A (en) * | 1993-10-07 | 1996-01-16 | Agouron Pharmaceuticals, Inc. | HIV protease inhibitors |
| JPH07248183A (en) * | 1994-03-11 | 1995-09-26 | Osaka Gas Co Ltd | Bathroom and clothing drying room |
| JP3298293B2 (en) * | 1994-03-14 | 2002-07-02 | 松下電器産業株式会社 | Garbage processing machine |
| WO1996028423A1 (en) * | 1995-03-15 | 1996-09-19 | Sankyo Company, Limited | Dipeptide compounds having ahpba structure |
| EP0983999B8 (en) * | 1995-09-26 | 2005-06-08 | Japan Tobacco Inc. | Process for producing amide derivatives and intermediates |
| US5962704A (en) * | 1995-09-26 | 1999-10-05 | Japan Tobacco Inc. | Production of amide derivatives and intermediate compounds therefor |
| PT984000E (en) * | 1995-09-26 | 2009-02-06 | Agouron Pharma | Process for producing amide derivatives and intermediate compounds |
| WO1997030993A1 (en) * | 1996-02-24 | 1997-08-28 | Basf Aktiengesellschaft | Pyrazole-4-yl-hetaroyl derivatives as herbicides |
-
1997
- 1997-04-09 UA UA99041906A patent/UA67727C2/en unknown
- 1997-09-04 CZ CZ20070084A patent/CZ298175B6/en not_active IP Right Cessation
- 1997-09-04 YU YU11599A patent/YU11599A/en unknown
- 1997-09-04 AP APAP/P/1999/001497A patent/AP1322A/en active
- 1997-09-04 CZ CZ0071699A patent/CZ298174B6/en not_active IP Right Cessation
- 1997-09-04 NZ NZ334909A patent/NZ334909A/en unknown
- 1997-09-04 AP APAP/P/2003/002938A patent/AP2003002938A0/en unknown
- 1997-09-04 EP EP03013275A patent/EP1361216B1/en not_active Expired - Lifetime
- 1997-09-04 GE GEAP19974736A patent/GEP20022799B/en unknown
- 1997-09-04 EE EEP199900109A patent/EE04465B1/en not_active IP Right Cessation
- 1997-09-04 EP EP97941402A patent/EP0927165B1/en not_active Expired - Lifetime
- 1997-09-04 SI SI9730719T patent/SI1361216T1/en unknown
- 1997-09-04 DE DE69734689T patent/DE69734689T2/en not_active Expired - Fee Related
- 1997-09-04 AT AT03013275T patent/ATE309990T1/en not_active IP Right Cessation
- 1997-09-04 SI SI9730605T patent/SI0927165T1/en unknown
- 1997-09-04 DK DK03013275T patent/DK1361216T3/en active
- 1997-09-04 EA EA199900257A patent/EA002051B1/en not_active IP Right Cessation
- 1997-09-04 HU HU0000028A patent/HUP0000028A3/en unknown
- 1997-09-04 ES ES03013275T patent/ES2252586T3/en not_active Expired - Lifetime
- 1997-09-04 PL PL331801A patent/PL198408B1/en not_active IP Right Cessation
- 1997-09-04 PL PL381445A patent/PL201758B1/en not_active IP Right Cessation
- 1997-09-04 SG SG200101308A patent/SG94780A1/en unknown
- 1997-09-04 BR BR9713192-0A patent/BR9713192A/en not_active Application Discontinuation
- 1997-09-04 ES ES97941402T patent/ES2210573T3/en not_active Expired - Lifetime
- 1997-09-04 DE DE69726298T patent/DE69726298T2/en not_active Expired - Fee Related
- 1997-09-04 CN CNB2004100073691A patent/CN1305854C/en not_active Expired - Fee Related
- 1997-09-04 TR TR1999/00473T patent/TR199900473T2/en unknown
- 1997-09-04 DK DK97941402T patent/DK0927165T3/en active
- 1997-09-04 WO PCT/US1997/015468 patent/WO1998009951A2/en active IP Right Grant
- 1997-09-04 SK SK90-2005A patent/SK285278B6/en not_active IP Right Cessation
- 1997-09-04 KR KR1019997001902A patent/KR100563289B1/en not_active Expired - Fee Related
- 1997-09-04 AT AT97941402T patent/ATE254603T1/en not_active IP Right Cessation
- 1997-09-04 JP JP51283198A patent/JP4149000B2/en not_active Expired - Fee Related
- 1997-09-04 CA CA002264756A patent/CA2264756A1/en not_active Abandoned
- 1997-09-04 CN CNB971984484A patent/CN1183117C/en not_active Expired - Fee Related
- 1997-09-04 AU AU43317/97A patent/AU740369B2/en not_active Ceased
- 1997-09-04 SK SK282-99A patent/SK284899B6/en not_active IP Right Cessation
- 1997-09-04 PT PT97941402T patent/PT927165E/en unknown
- 1997-09-04 IL IL12856797A patent/IL128567A/en not_active IP Right Cessation
-
1999
- 1999-02-19 IS IS4982A patent/IS2030B/en unknown
- 1999-03-03 OA OA9900049A patent/OA10988A/en unknown
- 1999-03-04 NO NO19991072A patent/NO313287B1/en not_active IP Right Cessation
- 1999-04-02 BG BG103305A patent/BG64793B1/en unknown
-
2002
- 2002-01-31 AU AU14736/02A patent/AU766155B2/en not_active Ceased
-
2006
- 2006-01-18 BG BG109411A patent/BG65237B1/en unknown
-
2007
- 2007-10-29 JP JP2007280974A patent/JP2008056693A/en not_active Withdrawn
- 2007-10-29 JP JP2007280975A patent/JP2008088178A/en active Pending
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