NZ334948A - Anthranilic acid derivatives as p-glycoprotein inhibitors useful for the treatment of multi drug-resistant cancers - Google Patents
Anthranilic acid derivatives as p-glycoprotein inhibitors useful for the treatment of multi drug-resistant cancersInfo
- Publication number
- NZ334948A NZ334948A NZ334948A NZ33494897A NZ334948A NZ 334948 A NZ334948 A NZ 334948A NZ 334948 A NZ334948 A NZ 334948A NZ 33494897 A NZ33494897 A NZ 33494897A NZ 334948 A NZ334948 A NZ 334948A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- ring
- halogen
- alkoxy
- r1or11
- Prior art date
Links
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003814 drug Substances 0.000 title abstract 2
- 229940049937 Pgp inhibitor Drugs 0.000 title 1
- 229940079593 drug Drugs 0.000 title 1
- 239000002748 glycoprotein P inhibitor Substances 0.000 title 1
- 208000016691 refractory malignant neoplasm Diseases 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 6
- -1 methylenedioxy Chemical group 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 abstract 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 abstract 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 abstract 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 abstract 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 abstract 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- YJSKZIATOGOJEB-UHFFFAOYSA-N thieno[2,3-b]pyrazine Chemical compound C1=CN=C2SC=CC2=N1 YJSKZIATOGOJEB-UHFFFAOYSA-N 0.000 abstract 2
- 229930192474 thiophene Natural products 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 abstract 1
- 108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 abstract 1
- 101100212791 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YBL068W-A gene Proteins 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 229940127089 cytotoxic agent Drugs 0.000 abstract 1
- 230000003013 cytotoxicity Effects 0.000 abstract 1
- 231100000135 cytotoxicity Toxicity 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000004060 metabolic process Effects 0.000 abstract 1
- 230000036457 multidrug resistance Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
An anthranilic acid derivative of formula (I), wherein: each of R, R1 and R2, which are the same or different, is H, C1-C6 alkyl, OH, C1-C6 alkoxy, halogen, nitro, or, N(R1OR11) wherein each of R1O and R11, which are the same or different, is H or C1-C6 alkyl, or R1 and R2, being attached to adjacent positions of ring b, together form a methylenedioxy or ethylenedioxy group; R3 is H or C1-C6 alkyl; R4 is C1-C6 alkyl or R4 represents -CH2- or -CH2CH2- which is attached either (i) to position 2 of ring b to complete a saturated 5- or 6-membered nitrogen-containing ring fused to ring b or (ii) to the position in ring a adjacent to that to which X, being a single bond, is linked, thereby completing a saturated 5- or 6-membered nitrogen-containing ring fused to ring a; R5 is H, OH or C1-C6 alkyl; X is a direct bond, 0, S, -S-(CH2)p- or -0-(CH2)p- wherein p is an integer of 1 to 6; R6 is H, C1-C6 alkyl or C1-C6 alkoxy; q is 0 or 1; Ar is an unsaturated carbocyclic or heterocyclic group selected from furan, thiophene, pyrrole, indole, isoindole, pyrazole, imidazole, isoxazole, oxazole, isothiazole, thiazole, pyridine, quinoline, quinoxaline, isoquinoline, thienopyrazine, pyran, pyrimidine, pyridazine, pyrazine, purine and triazine which is unsubstituted or substituted by one or more substituents selected from OH, halogen, C1-C6 alkyl, which is unsubstituted or substituted by halogen, C1-C6 alkoxy, nitro and N(R1OR11); each of R7 and R8, which are the same or different, is H, C1-C6 alkyl which is unsubstituted or substituted by one or more halogen atoms, C1-C6 alkoxy, hydroxy, halogen, phenyl, NHOH, nitro, N(R1OR11), or SR12 wherein R12 is H or C1-C6 alkyl; or R7 and R8, when situated on adjacent carbon atoms, form together with the carbon atoms to which they are attached a benzene ring or a methylenedioxy substituent; R9 is phenyl or an unsaturated heterocyclic group selected from furan, thiophene, pyrrole, indole, isoindole, pyrazole, imidazole, isoxazole, oxazole, isothiazole, thiazole, pyridine, quinoline, quinoxaline, isoquinoline, thienopyrazine, pyran, pyrimidine, pyridazine, pyrazine, purine and triazine, each of which is unsubstituted or substituted by C1-C6 alkyl, OH, C1-C alkoxy, halogen, C3-C6 cycloalkyl, phenyl, benzyl, trifluoromethyl, nitro, acetyl, benzoyl or N(R1OR11), or two substituents on adjacent ring positions of the phenyl or heterocyclic group together complete a saturated or unsaturated 6-membered ring or form a methylenedioxy group; n is 0 or 1; and m is 0 or an integer of 1 to 6; Also disclosed are pharmaceutical compositions containing the above compound that can be used as an inhibitor of p-glycoprotein. The compound is useful as a modulator for multidrug resistance, for potentiating the cytotoxicity of a chemotherapeutic agent or enhancing the net absorption, distribution, metabolism or elimination characteristics of a therapeutic agent
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9602552 | 1996-10-18 | ||
| GBGB9717576.4A GB9717576D0 (en) | 1997-08-19 | 1997-08-19 | Pharmaceutical compounds |
| PCT/GB1997/002885 WO1998017648A1 (en) | 1996-10-18 | 1997-10-17 | Anthranilic acid derivatives as multi drug resistance modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ334948A true NZ334948A (en) | 2000-11-24 |
Family
ID=26308635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ334948A NZ334948A (en) | 1996-10-18 | 1997-10-17 | Anthranilic acid derivatives as p-glycoprotein inhibitors useful for the treatment of multi drug-resistant cancers |
Country Status (5)
| Country | Link |
|---|---|
| MY (1) | MY118642A (en) |
| NZ (1) | NZ334948A (en) |
| RU (1) | RU2195454C2 (en) |
| SK (1) | SK284649B6 (en) |
| UA (1) | UA67730C2 (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU1750166C (en) * | 1982-11-28 | 1995-10-20 | Акционерное общество "Научно-исследовательский и проектный институт мономеров с опытным заводом" | Method of synthesis of methylene-bis-anthranilic acid |
| NZ212525A (en) * | 1985-06-24 | 1989-02-24 | Dfc New Zealand Ltd Formerly D | Nitrogen-containing heterocyclic compounds, and pharmaceutical compositions containing such |
| KR100220538B1 (en) * | 1991-01-11 | 1999-09-15 | 뮈쉘 쥐르밀 | Acridine derivatives |
| US5663179A (en) * | 1992-07-10 | 1997-09-02 | Laboratoires Glaxo Sa | Certain isoquinoline derivatives having anti-tumor properties |
-
1997
- 1997-10-16 MY MYPI97004871A patent/MY118642A/en unknown
- 1997-10-17 UA UA99042118A patent/UA67730C2/en unknown
- 1997-10-17 RU RU99109990/04A patent/RU2195454C2/en not_active IP Right Cessation
- 1997-10-17 NZ NZ334948A patent/NZ334948A/en unknown
- 1997-10-17 SK SK509-99A patent/SK284649B6/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MY118642A (en) | 2004-12-31 |
| UA67730C2 (en) | 2004-07-15 |
| SK284649B6 (en) | 2005-08-04 |
| RU2195454C2 (en) | 2002-12-27 |
| SK50999A3 (en) | 2000-08-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |