NZ334127A - Cryptophycin compounds which disrupt microtubulin systems - Google Patents
Cryptophycin compounds which disrupt microtubulin systemsInfo
- Publication number
- NZ334127A NZ334127A NZ334127A NZ33412797A NZ334127A NZ 334127 A NZ334127 A NZ 334127A NZ 334127 A NZ334127 A NZ 334127A NZ 33412797 A NZ33412797 A NZ 33412797A NZ 334127 A NZ334127 A NZ 334127A
- Authority
- NZ
- New Zealand
- Prior art keywords
- group
- alkyl
- ring
- lower alkyl
- hydrogen
- Prior art date
Links
- PSNOPSMXOBPNNV-VVCTWANISA-N cryptophycin 1 Chemical class C1=C(Cl)C(OC)=CC=C1C[C@@H]1C(=O)NC[C@@H](C)C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@H](C)[C@@H]2[C@H](O2)C=2C=CC=CC=2)C/C=C/C(=O)N1 PSNOPSMXOBPNNV-VVCTWANISA-N 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 125000001072 heteroaryl group Chemical group 0.000 abstract 3
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 206010017533 Fungal infection Diseases 0.000 abstract 1
- 208000031888 Mycoses Diseases 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000006307 alkoxy benzyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 229940034982 antineoplastic agent Drugs 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 125000004069 aziridinyl group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 150000002118 epoxides Chemical group 0.000 abstract 1
- 125000006498 halo alkoxy benzyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000006289 hydroxybenzyl group Chemical group 0.000 abstract 1
- -1 or OR31 Chemical compound 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003553 thiiranes Chemical group 0.000 abstract 1
- 125000005208 trialkylammonium group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The cryptophycin compounds of formula I disrupt microtubulin systems. The compounds can be used as anti-neoplastic agents and for treating fungal infections. In formula I; Ar is selected from the group consisting of phenyl, any simple unsubstituted aromatic, simple substituted aromatic, optionally substituted heteroaromatic group, heterocyclic, C1-12 alkyl, C2-12 alkenyl, C2-12 alkynyl, NR51R52, COR52, OR53 or other group; wherein R51 is selected from the group consisting of hydrogen and C1-3 alkyl; R52 is selected from the group consisting of hydrogen and C1-3 alkyl; R53 is selected from the group consisting of C1-12 alkyl; R1 and R2 are each independently selected from the group consisting of halogen, monalkylamino, dialkylamino, trialkylammonium, alkylthio, dialkylsulfonium, sulfate, phosphate, or OR31, SR31, NR31, OH, SH, or other group; wherein R31is P, S, C1-12 alkyl, B, an amino acid or other group; or R1 and R2 may be taken together with C-18 and C-19 to form an epoxide ring, an aziridine ring, an episulfide ring, a sulfate ring, a cyclopropyl ring or mono(C1-6)alkyl-phosphate ring; or R1 and R2 may be taken together to form a second bond between C-18 and C-19; R3 is a lower alkyl group; R4 is H or OH; R5 is H or OH; or R4 and R5 may be taken together to form a second bond between C13 and C14; R6 is a substituent selected from the group consisting of benzyl, hydroxybenzyl, alkoxybenzyl, halohydroxybenzyl, dihalohydroxybenzyl, haloalkoxybenzyl, or dihaloalkyoxybenzyl group, B-ring heteroaromatic, substituted heteroaromatic, B-ring (C1-6 alkyl, (C3-8) cycloalkyl, substituted C3-8 cycloalkyl, substituted (C1-6) alkyl, or other group; R7 is selected from the group consisting of NR51R52, R53NR51R57, OR53, H and a lower alkyl group; wherein R57 is H, halogen or C1-12 alkyl; R8 is H or a lower alkyl group; or R7 and R8 can form a cyclopropyl ring; R9 is selected from the group consisting of H, a lower alkyl group, unsaturated lower alkyl, lower alkyl-C3-5 cycloalkyl, and benzyl; R10 is H or a lower alkyl group; R11 is selected from the group consisting of hydrogen, OH, lower alkyl group, optionally substituted phenyl, or optionally substituted benzyl; Rl4 is selected from the group consisting of hydrogen and lower alkyl; R30 is hydrogen or C1-6 alkyl; or R30 may be taken together with the N at C-ll to form a 3 to 7 membered cyclic ring; R50 is hydrogen or a carbonyl group; X is selected from the group consisting of 0, C, S, NH and alkylamino; and Y is selected from the group consisting of C, O, NH, S, SO, SO2 and alkylamino.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2581696P | 1996-08-30 | 1996-08-30 | |
| US3953097P | 1997-03-03 | 1997-03-03 | |
| US4002997P | 1997-03-04 | 1997-03-04 | |
| US3905697P | 1997-03-10 | 1997-03-10 | |
| PCT/US1997/015240 WO1998008505A1 (en) | 1996-08-30 | 1997-08-29 | Pharmaceutical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ334127A true NZ334127A (en) | 2000-07-28 |
Family
ID=27487440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ334127A NZ334127A (en) | 1996-08-30 | 1997-08-29 | Cryptophycin compounds which disrupt microtubulin systems |
Country Status (4)
| Country | Link |
|---|---|
| KR (1) | KR100505779B1 (en) |
| HU (1) | HU227195B1 (en) |
| NZ (1) | NZ334127A (en) |
| PL (1) | PL331919A1 (en) |
-
1997
- 1997-08-29 HU HU9904141A patent/HU227195B1/en not_active IP Right Cessation
- 1997-08-29 KR KR10-1999-7001655A patent/KR100505779B1/en active IP Right Grant
- 1997-08-29 PL PL97331919A patent/PL331919A1/en unknown
- 1997-08-29 NZ NZ334127A patent/NZ334127A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL331919A1 (en) | 1999-08-16 |
| HUP9904141A1 (en) | 2000-03-28 |
| HUP9904141A3 (en) | 2001-08-28 |
| KR20000035919A (en) | 2000-06-26 |
| KR100505779B1 (en) | 2005-08-04 |
| HU227195B1 (en) | 2010-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RENW | Renewal (renewal fees accepted) | ||
| ASS | Change of ownership |
Owner name: WAYNE STATE UNIVERSITY, US Free format text: OLD OWNER(S): ELI LILLY AND COMPANY; UNIVERSITY OF HAWAII; WAYNE STATE UNIVERSITY Owner name: UNIVERSITY OF HAWAII, US Free format text: OLD OWNER(S): ELI LILLY AND COMPANY; UNIVERSITY OF HAWAII; WAYNE STATE UNIVERSITY |
|
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| EXPY | Patent expired |