AU707644B2 - Cyclopropylindoles and their seco precursors, and their use as prodrugs - Google Patents
Cyclopropylindoles and their seco precursors, and their use as prodrugs Download PDFInfo
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- AU707644B2 AU707644B2 AU67109/96A AU6710996A AU707644B2 AU 707644 B2 AU707644 B2 AU 707644B2 AU 67109/96 A AU67109/96 A AU 67109/96A AU 6710996 A AU6710996 A AU 6710996A AU 707644 B2 AU707644 B2 AU 707644B2
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- 238000010369 molecular cloning Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 210000005170 neoplastic cell Anatomy 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- UOWVMDUEMSNCAV-WYENRQIDSA-N rachelmycin Chemical compound C1([C@]23C[C@@H]2CN1C(=O)C=1NC=2C(OC)=C(O)C4=C(C=2C=1)CCN4C(=O)C1=CC=2C=4CCN(C=4C(O)=C(C=2N1)OC)C(N)=O)=CC(=O)C1=C3C(C)=CN1 UOWVMDUEMSNCAV-WYENRQIDSA-N 0.000 description 1
- 239000012217 radiopharmaceutical Substances 0.000 description 1
- 229940121896 radiopharmaceutical Drugs 0.000 description 1
- 230000002799 radiopharmaceutical effect Effects 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000001177 retroviral effect Effects 0.000 description 1
- 150000008223 ribosides Chemical class 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000002741 site-directed mutagenesis Methods 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- SJMDMGHPMLKLHQ-UHFFFAOYSA-N tert-butyl 2-aminoacetate Chemical compound CC(C)(C)OC(=O)CN SJMDMGHPMLKLHQ-UHFFFAOYSA-N 0.000 description 1
- UCERYJRYDLVOAD-UHFFFAOYSA-N tert-butyl 2-chloro-5-nitrobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC([N+]([O-])=O)=CC=C1Cl UCERYJRYDLVOAD-UHFFFAOYSA-N 0.000 description 1
- KIDSZNLTRZMEIH-UHFFFAOYSA-N tert-butyl 3-(chloromethyl)-6-nitro-2,3-dihydroindole-1-carboxylate Chemical compound C1=C([N+]([O-])=O)C=C2N(C(=O)OC(C)(C)C)CC(CCl)C2=C1 KIDSZNLTRZMEIH-UHFFFAOYSA-N 0.000 description 1
- YRFIRTPJPOONQE-UHFFFAOYSA-N tert-butyl 3-(hydroxymethyl)-6-nitro-2,3-dihydroindole-1-carboxylate Chemical compound C1=C([N+]([O-])=O)C=C2N(C(=O)OC(C)(C)C)CC(CO)C2=C1 YRFIRTPJPOONQE-UHFFFAOYSA-N 0.000 description 1
- DUNFNBQQWYQKFE-UHFFFAOYSA-N tert-butyl 4-formylbenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(C=O)C=C1 DUNFNBQQWYQKFE-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 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
- C07D401/14—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 three or more hetero rings
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9516943.9A GB9516943D0 (en) | 1995-08-18 | 1995-08-18 | Novel cyclopropylindoles and their secoprecursors,and their use as prodrugs |
| GB9516943 | 1995-08-18 | ||
| PCT/NZ1996/000083 WO1997007097A1 (en) | 1995-08-18 | 1996-08-19 | Cyclopropylindoles and their seco precursors, and their use as prodrugs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU6710996A AU6710996A (en) | 1997-03-12 |
| AU707644B2 true AU707644B2 (en) | 1999-07-15 |
Family
ID=10779431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU67109/96A Ceased AU707644B2 (en) | 1995-08-18 | 1996-08-19 | Cyclopropylindoles and their seco precursors, and their use as prodrugs |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5985909A (https=) |
| EP (1) | EP0850220A1 (https=) |
| JP (1) | JPH11511113A (https=) |
| AU (1) | AU707644B2 (https=) |
| CA (1) | CA2229264A1 (https=) |
| GB (1) | GB9516943D0 (https=) |
| NZ (1) | NZ315410A (https=) |
| WO (1) | WO1997007097A1 (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ334344A (en) * | 1996-09-12 | 2000-08-25 | Cancer Res Campaign Tech | benzo[e]indole and pyrrolo[3,2-e]indole compounds and their use as prodrugs |
| US6130237A (en) * | 1996-09-12 | 2000-10-10 | Cancer Research Campaign Technology Limited | Condensed N-aclyindoles as antitumor agents |
| GB9712370D0 (en) | 1997-06-14 | 1997-08-13 | Aepact Ltd | Therapeutic systems |
| EP0887348A1 (en) * | 1997-06-25 | 1998-12-30 | Boehringer Mannheim Italia S.p.A. | Bis-Indole derivatives having antimetastatic activity, a process for their preparation and pharmaceutical compositions containing them |
| US6410584B1 (en) * | 1998-01-14 | 2002-06-25 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells with indole derivatives |
| GB9818730D0 (en) | 1998-08-27 | 1998-10-21 | Univ Portsmouth | Collections of compounds |
| DE69930328T2 (de) | 1998-08-27 | 2006-12-14 | Spirogen Ltd., Ryde | Dimere Pyrrolobenzodiazepine |
| US6909006B1 (en) * | 1999-08-27 | 2005-06-21 | Spirogen Limited | Cyclopropylindole derivatives |
| EP2357009A1 (en) | 2002-07-15 | 2011-08-17 | Board of Regents, The University of Texas System | Duramycin peptide binding to anionic phospholipids and aminophospholipids conjugates and their use in treating viral infections |
| GB0226593D0 (en) | 2002-11-14 | 2002-12-24 | Consultants Ltd | Compounds |
| ZA200507752B (en) * | 2003-03-28 | 2007-01-31 | Threshold Pharmaceuticals Inc | Compositions and methods for treating cancer |
| GB0321295D0 (en) | 2003-09-11 | 2003-10-15 | Spirogen Ltd | Synthesis of protected pyrrolobenzodiazepines |
| CN102746336B (zh) | 2005-06-29 | 2015-08-19 | 施瑞修德制药公司 | 氨基磷酸酯烷化剂前体药物 |
| EP1994000B1 (en) * | 2006-02-02 | 2017-08-23 | Syntarga B.V. | Water-soluble cc-1065 analogs and their conjugates |
| GB0619325D0 (en) * | 2006-09-30 | 2006-11-08 | Univ Strathclyde | New compounds |
| EP2114157B1 (en) * | 2006-12-26 | 2021-05-26 | ImmunoGenesis, Inc. | Phosphoramidate alkylator prodrug for the treatment of cancer |
| US9901567B2 (en) | 2007-08-01 | 2018-02-27 | Syntarga B.V. | Substituted CC-1065 analogs and their conjugates |
| US20090118031A1 (en) * | 2007-11-01 | 2009-05-07 | Qualizza Gregory K | Shaft Structure with Configurable Bending Profile |
| ES2572356T3 (es) | 2007-11-09 | 2016-05-31 | Peregrine Pharmaceuticals Inc | Composiciones de anticuerpos dirigidos contra VEGF y procedimientos |
| UY31506A1 (es) * | 2007-12-03 | 2009-08-03 | Derivados de indolinona y procedimiento para su preparacion | |
| AU2009320481C1 (en) | 2008-11-03 | 2016-12-08 | Syntarga B.V. | Novel CC-1065 analogs and their conjugates |
| AU2011243294C1 (en) | 2010-04-21 | 2015-12-03 | Syntarga B.V. | Novel conjugates of CC-1065 analogs and bifunctional linkers |
| US9056874B2 (en) | 2012-05-04 | 2015-06-16 | Novartis Ag | Complement pathway modulators and uses thereof |
| EP2970269B1 (en) | 2013-03-14 | 2017-04-19 | Novartis AG | 2-(1h-indol-4-ylmethyl)-3h-imidazo[4,5-b]pyridine-6-carbonitrile derivatives as complement factor b inhibitors useful for the treatment of ophthalmic diseases |
| EP3089963A1 (en) | 2013-10-30 | 2016-11-09 | Novartis AG | 2-benzyl-benzimidazole complement factor b inhibitors and uses thereof |
| AU2015205574B2 (en) | 2014-01-10 | 2019-08-15 | Byondis B.V. | Method for purifying Cys-linked antibody-drug conjugates |
| AU2022238571A1 (en) | 2021-03-18 | 2023-09-14 | Seagen Inc. | Selective drug release from internalized conjugates of biologically active compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0340243B1 (en) * | 1986-12-19 | 1994-09-28 | The Upjohn Company | Cc-1065 analogs |
| GB8705477D0 (en) * | 1987-03-09 | 1987-04-15 | Carlton Med Prod | Drug delivery systems |
| GB8919607D0 (en) * | 1989-08-30 | 1989-10-11 | Wellcome Found | Novel entities for cancer therapy |
| AU648313B2 (en) * | 1990-04-25 | 1994-04-21 | Pharmacia & Upjohn Company | Novel CC-1065 analogs |
| CA2122036C (en) * | 1991-10-23 | 2002-09-17 | Gillian Anlezark | Bacterial nitroreductase for the reduction of cb 1954 and analogues thereof to a cytotoxic form |
| NZ240785A (en) * | 1991-11-28 | 1995-08-28 | Cancer Res Campaign Tech | Substituted nitro aniline derivatives and medicaments |
| GB9314960D0 (en) * | 1992-07-23 | 1993-09-01 | Zeneca Ltd | Chemical compounds |
| GB9323008D0 (en) * | 1993-11-05 | 1994-01-05 | Connors Thomas | Improvements relating to cancer therapy |
-
1995
- 1995-08-18 GB GBGB9516943.9A patent/GB9516943D0/en active Pending
-
1996
- 1996-08-19 CA CA002229264A patent/CA2229264A1/en not_active Abandoned
- 1996-08-19 US US09/011,883 patent/US5985909A/en not_active Expired - Fee Related
- 1996-08-19 WO PCT/NZ1996/000083 patent/WO1997007097A1/en not_active Ceased
- 1996-08-19 JP JP8531337A patent/JPH11511113A/ja not_active Withdrawn
- 1996-08-19 EP EP96927217A patent/EP0850220A1/en not_active Withdrawn
- 1996-08-19 NZ NZ315410A patent/NZ315410A/xx unknown
- 1996-08-19 AU AU67109/96A patent/AU707644B2/en not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| J. AM. CHEM. SOC (1990) 112, PAGES 8961-8971 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US5985909A (en) | 1999-11-16 |
| GB9516943D0 (en) | 1995-10-18 |
| AU6710996A (en) | 1997-03-12 |
| WO1997007097A1 (en) | 1997-02-27 |
| EP0850220A1 (en) | 1998-07-01 |
| NZ315410A (en) | 1999-07-29 |
| CA2229264A1 (en) | 1997-02-27 |
| JPH11511113A (ja) | 1999-09-28 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PC | Assignment registered |
Owner name: AUCKLAND UNISERVICES LIMITED Free format text: FORMER OWNER WAS: CANCER RESEARCH CAMPAIGN TECHNOLOGY LIMITED |