WO1994020463A1 - Novel distamycin analogues - Google Patents
Novel distamycin analogues Download PDFInfo
- Publication number
- WO1994020463A1 WO1994020463A1 PCT/EP1994/000557 EP9400557W WO9420463A1 WO 1994020463 A1 WO1994020463 A1 WO 1994020463A1 EP 9400557 W EP9400557 W EP 9400557W WO 9420463 A1 WO9420463 A1 WO 9420463A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pyrrol
- methyl
- carboxyamido
- chloroethyl
- bis
- Prior art date
Links
- 0 C*C1=CC(C)C(*)=C1 Chemical compound C*C1=CC(C)C(*)=C1 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/14—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
Definitions
- n is 0 or an integer ranging from 1 to 4 is 0 or an integer ranging from 1 to 4 A is selected from the group consisting of : acyclic, aromatic or heterocyclic residue
- B is selected from the group consisting of : a simple chemical bond, -C0-NH-CH(R 3 )-, -NH-C0-CH(R 3 )- wherein R ⁇ is H or the side chain of a natural alpha-aminocarboxylic acid;
- Antibiotic dystamicine is a known compound of formula (II) :
- antiviral and antitumoral agents nowadays used in therapy are characterized by serious side effects, limiting their use in a large number of cases which on the contrary should take advantage from the therapy; moreover therapeutical progresses are necessary in the clinical treatment of important solid tumors, as for example pulmonary tumors and ovarian tumors, not responding adequately to any treatment nowadays in use.
- a requisite for the therapeutic progress in this particular field is therefore the discovery of compounds having molecular moieties allowing them to increase the selectivity in inhibiting viral proliferation and the proliferation of tumoral rather than healthy cells.
- the present invention has the aim to render available new antitumoral and antiviral compounds and in particular compounds
- the invention refers to pharmaceutical compositions containing the above mentioned compounds , or pharmaceutically acceptable salts thereof formed with inorganic acids such as hydrochloric, hydrobromic, sulfuric, nitric and the like or with organic acids such as acetic, propionic, succinic, malonic, citric, tartaric, ethansulfonic, p-toluensulfonic and the like.
- inorganic acids such as hydrochloric, hydrobromic, sulfuric, nitric and the like
- organic acids such as acetic, propionic, succinic, malonic, citric, tartaric, ethansulfonic, p-toluensulfonic and the like.
- n is as above defined m is zero or an integer comprised between 1 and 3>
- A cyclohexyl, p-phenylene, 1-methylpyrrole, thiophene, thiazole, imidazole, furan, isoxazole, oxazole, triazole, pyridine, pyrrole.
- B is a simple bond, or when it is a -CO-NH-CH(R )- group or a -NH-
- R is preferably methyl, isobutyl, sec-butyl, hydroxymethyl , mercaptomethyl , carbamoylmethyl , benzyl, 4- hydroxybenzyl , 5-imidazolylmethyl, 2-carbamoylethyl , 2- methylthioethyl, 1-hydroxyethyl, 3 ⁇ guanidinopropyl , 4-aminobutyl R ⁇ and R 2 represent preferably an ethyl group, 2-hydroxyethyl , 2- chloroethyl , methansulf onylethyl .
- B is a chemical bond or the -NHCOCH(R )- group, wherein R? is as above defined, and m, A, R ⁇ and R 2 are as above defined, with a compound of formula (VI)
- DCC diclohexylcarbodiimide
- EDC l-dimethylaminopropyl
- hydrochlorate hydroxybenzotriazole or BOP (benzotriazol-1- iloxy(dimethylaminophosphoniumhexafluoride phosphate) or by using a reactive derivative of the acids (III) and (IV) as for example an acylchloride , an acylimidazole , an acylazide or an active ester, such as 2, 4 , 5 trichlorophenoxyester or N-oxysuccinimidoester, or an anhydride thereof .
- condensing agents as DCC (dicyclohexylcarbodiimide) or EDC [l-dimethylaminopropyl) -3 ⁇ ethylcarbodiimide hydrochlorate]
- BOP benzotriazol-1- iloxy(dimethylaminophosphoniumhexafluoride phosphat
- amidation reactions are carried out using molar ratio of from 1 : 1 to 1 :3 in an inert organic solvent as for example dimethyl sulf oxide , hexamethyl phosphotriamide , dimethylacetamide , or preferably dimethyl formamide in the presence of a condensing agent as above described and of N- hydroxybenzotriazole or BOP and in the presence of an organic base as triethylamine , diisopropylethylamine and l , 8-bis (dimethylamino) - naphthalene.
- an inert organic solvent as for example dimethyl sulf oxide , hexamethyl phosphotriamide , dimethylacetamide , or preferably dimethyl formamide in the presence of a condensing agent as above described and of N- hydroxybenzotriazole or BOP and in the presence of an organic base as triethylamine , diisopropylethylamine and l , 8-bis
- the reaction temperature may be comprised between -10 C and 50 C and the time required for the reaction ranges from 2 to 48 hours .
- the reaction of the compound of formula ( III) or the compound of formula (VII) with the compound, of formula ( IV) may be carried out using a reactive derivative of the compound of formula ( III) or of the compound of formula (VII ) of the above mentioned type , and therefore accomplishing the reaction in a biphasic system water- organic solvent as Schotten-Baumann amidation or in an organic solvent as for example a hydroxyde, a carbonate or a bicarbonate of an alkaline metal , preferably sodium , potassium , barium or an organic base as triethylamine, diisopropylamine , pyridine or N,N dimethylaminopyridine .
- a compound of formula ( IX) wherein A, m, R ⁇ , R R and Re are as above defined can be prepared by reacting a compound of formula (VIII) wherein A, m, R 1 and R 2 are as above defined or its reactive derivative with a compound of formula (X)
- a reactive compound of an acid of formula (VIII) can be the same already reported in the present application for the compound of formula (III) or for the compound of formula (VII) and the reaction can be accomplished under similar conditions to those reported for the amidation reaction of a compound of formula (III) or a compound of formula (VII) with a compound of formula (IV).
- the compounds of formula (X) either are commercially available or can be prepared by the conventional processes starting from the corresponding aminoacids as described for example in E. Gross, J. Meienhofer, The Peptides V. 3, p. 102-132, 198I, Academic Press.
- A, R ⁇ and R are as above defined, namely compounds of formula (XI)
- a compound having formula (XII) wherein A, m, R- R 2 , R and Rg are as above defined can be prepared by reacting a compound of formula
- a reactive derivative of an acid of formula (XIII) can be the same as reported in this application for the compound having formula (III) or for the compound having formula (VII) and the reaction can be carried out under similar conditions to those reported for the amidation reaction of a compound of formula (III) or a compound of formula (VII) with a compound of formula (IV).
- a compound of formula (IV) either is a commercially available compound or can be prepared by the known methods [Gazzetta Chimica Italiana, 99, 632 (1969)].
- a compound of formula (VI) can be prepared according to the methods described in the International Patent application No. WO 93/13739 published on 22nd July 1993 in the name of the same applicant and herein reported by reference.
- the compounds of the present invention have antitumoral and antiviral activity, in particular they show high cytotoxicity levels against the tumoral cellular lines.
- the present invention relates to pharmaceutical compositions comprising as active principle a compound of general formula (I) or a pharmaceutically acceptable salt thereof with a pharmaceutically acceptable vehicle or diluent.
- a therapeutically effective amount of the compound of formula (I) according to the invention is combined with an inert and pharmaceutically acceptable vehicle.
- Conventional vehicles can be used and the compositions can be prepared using the conventional techniques.
- the compounds according to the present invention are useful for human and animal therapeutical treatment.
- the compounds according to the present invention are useful as antitumoral and / or antiviral agents when administered to patients in a therapeutically effective amount, for example a suitable dosage for the administation to adult patients can vary from about 0.1 and 100 mg per unitary dose from one to 4 times a day.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6519534A JPH08508720A (ja) | 1993-03-01 | 1994-02-25 | ピロールーアミジン化合物およびその薬剤的に受容できる塩、その製造法ならびにこれを含む医薬組成物 |
KR1019950703699A KR960701007A (ko) | 1993-03-01 | 1994-02-25 | 피롤-아미딘계 화합물 및 약제학적으로 허용 가능한 그 염, 그 제조방법 및 상기 화합물을 포함하는 약제조성물 |
EP94909068A EP0690840A1 (en) | 1993-03-01 | 1994-02-25 | Novel distamycin analogues |
AU62068/94A AU6206894A (en) | 1993-03-01 | 1994-02-25 | Novel distamycin analogues |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITFI93A000030 | 1993-03-01 | ||
ITFI930030A IT1271456B (it) | 1993-03-01 | 1993-03-01 | Composti pirrol-amidinici, e loro sali farmaceuticamente accettabili, processi di preparazione e composizioni farmaceutiche che li contengono |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1994020463A1 true WO1994020463A1 (en) | 1994-09-15 |
WO1994020463B1 WO1994020463B1 (en) | 1994-10-27 |
Family
ID=11350335
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1994/000557 WO1994020463A1 (en) | 1993-03-01 | 1994-02-25 | Novel distamycin analogues |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP0690840A1 (it) |
JP (1) | JPH08508720A (it) |
KR (1) | KR960701007A (it) |
AU (1) | AU6206894A (it) |
CA (1) | CA2157187A1 (it) |
IT (1) | IT1271456B (it) |
WO (1) | WO1994020463A1 (it) |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996005196A1 (en) * | 1994-08-08 | 1996-02-22 | Pharmacia S.P.A. | Distamycin a analogues as antitumour or antiviral agents |
WO1998021202A1 (en) * | 1996-11-11 | 1998-05-22 | Pharmacia & Upjohn S.P.A. | Benzoheterocyclic distamycin derivatives, process for preparing them, and their use as antitumor and antiviral agents |
WO1999050266A1 (en) * | 1998-03-27 | 1999-10-07 | Pharmacia & Upjohn S.P.A. | Benzoheterocyclic distamycin derivatives, process for preparing them, and their use as antitumor agents |
US5998140A (en) * | 1996-07-31 | 1999-12-07 | The Scripps Research Institute | Complex formation between dsDNA and oligomer of cyclic heterocycles |
WO2000006541A1 (en) * | 1998-07-30 | 2000-02-10 | Pharmacia & Upjohn S.P.A. | Sulfurated distamycin derivatives, process for preparing them, and their use as antitumor agents |
US6090947A (en) * | 1996-02-26 | 2000-07-18 | California Institute Of Technology | Method for the synthesis of pyrrole and imidazole carboxamides on a solid support |
US6143901A (en) * | 1996-07-31 | 2000-11-07 | Genesoft, Inc. | Complex formation between dsDNA and pyrrole imidazole polyamides |
US6472537B1 (en) | 1996-02-26 | 2002-10-29 | California Institute Of Technology | Polyamides for binding in the minor groove of double stranded DNA |
US6506906B1 (en) | 1996-02-26 | 2003-01-14 | California Institute Of Technology | Preparation and use of bifunctional molecules having DNA sequence binding specificity |
US6555692B1 (en) | 1996-02-26 | 2003-04-29 | California Institute Of Technology | Preparation and use of bifunctional molecules having DNA sequence binding specificity |
US6555693B2 (en) | 2000-03-16 | 2003-04-29 | Genesoft, Inc. | Charged compounds comprising a nucleic acid binding moiety and uses therefor |
US6559125B1 (en) | 2000-01-28 | 2003-05-06 | California Institute Of Technology | Polyamide-alkylator conjugates and related products and method |
US6635417B1 (en) | 1996-07-31 | 2003-10-21 | California Institute Of Technology | Complex formation between DSDNA and oligomer of cyclic heterocycles |
US7049061B1 (en) | 1996-02-26 | 2006-05-23 | California Institute Of Technology | Stereochemical control of the DNA binding affinity, sequence specificity, and orientation-preference of chiral hairpin polyamides in the minor groove |
US7078536B2 (en) | 2001-03-14 | 2006-07-18 | Genesoft Pharmaceuticals, Inc. | Charged compounds comprising a nucleic acid binding moiety and uses therefor |
US7122626B2 (en) | 2001-04-26 | 2006-10-17 | Genesoft Pharmceuticals, Inc. | Halogen-substitued thienyl compounds |
US7129214B2 (en) | 2002-12-10 | 2006-10-31 | Oscient Pharmaceuticals Corporation | Antibacterial compounds having a (pyrrole carboxamide)-(benzamide)-(imidazole carboxamide) motif |
US7265129B2 (en) | 2002-10-25 | 2007-09-04 | Genesoft Pharmaceuticals, Inc. | Anti-infective biaryl compounds |
US7348427B2 (en) | 2001-06-13 | 2008-03-25 | Genesoft Pharmaceuticals, Inc. | Antipathogenic benzamide compounds |
US7498349B2 (en) | 2002-08-02 | 2009-03-03 | Genesoft Pharmaceuticals, Inc. | Biaryl compounds having anti-infective activity |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0246868A1 (en) * | 1986-05-20 | 1987-11-25 | FARMITALIA CARLO ERBA S.r.l. | Site specific alkylating agents |
EP0388948A1 (en) * | 1989-03-23 | 1990-09-26 | FARMITALIA CARLO ERBA S.r.l. | Acryloyl substituted pyrrole derivatives |
WO1993013739A2 (en) * | 1992-01-10 | 1993-07-22 | A. Menarini Industrie Farmaceutiche Riunite S.R.L. | Retroreverse pyrrole-amidino oligopeptide anticancer agent analogues, preparation of same, and pharmaceutical compositions containing such analogues |
-
1993
- 1993-03-01 IT ITFI930030A patent/IT1271456B/it active IP Right Grant
-
1994
- 1994-02-25 EP EP94909068A patent/EP0690840A1/en not_active Withdrawn
- 1994-02-25 KR KR1019950703699A patent/KR960701007A/ko not_active Application Discontinuation
- 1994-02-25 CA CA002157187A patent/CA2157187A1/en not_active Abandoned
- 1994-02-25 AU AU62068/94A patent/AU6206894A/en not_active Abandoned
- 1994-02-25 WO PCT/EP1994/000557 patent/WO1994020463A1/en not_active Application Discontinuation
- 1994-02-25 JP JP6519534A patent/JPH08508720A/ja active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0246868A1 (en) * | 1986-05-20 | 1987-11-25 | FARMITALIA CARLO ERBA S.r.l. | Site specific alkylating agents |
EP0388948A1 (en) * | 1989-03-23 | 1990-09-26 | FARMITALIA CARLO ERBA S.r.l. | Acryloyl substituted pyrrole derivatives |
WO1993013739A2 (en) * | 1992-01-10 | 1993-07-22 | A. Menarini Industrie Farmaceutiche Riunite S.R.L. | Retroreverse pyrrole-amidino oligopeptide anticancer agent analogues, preparation of same, and pharmaceutical compositions containing such analogues |
Non-Patent Citations (3)
Title |
---|
ARCAMONE, F.; LAZZARI, E.; MENOZZI, M.; SORANZO, C.; VERINI, M. A.: "Synthesis, DNA binding and antiviral activity of distamycin analogs containing different heterocyclic moieties", ANTI-CANCER DRUG DES., vol. 1, no. 3, 1986, pages 235 - 244 * |
ARCAMONE, FEDERICO MARIA; ANIMATI, FABIO; BARBIERI, BRUNELLA; CONFIGLIACCHI, EMANUELA; D'ALESSIO, ROBERTO; GERONI, CRISTINA; GIULI: "Synthesis, DNA-binding properties, and antitumor activity of novel distamycin derivatives", JOURNAL OF MEDICINAL CHEMISTRY., vol. 32, no. 4, 1989, WASHINGTON US, pages 774 - 778 * |
MONTECUCCO, ALESSANDRA; LESTINGI, MARTA; ROSSIGNOL, JEAN MICHEL; ELDER, RHODERICK H.; CIARROCCHI, GIOVANNI: "Lack of discrimination between DNA ligases I and III by two classes of inhibitors, anthracyclines and distamycins", BIOCHEM. PHARMACOLOG., vol. 45, no. 7, 1993, pages 1536 - 1539 * |
Cited By (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996005196A1 (en) * | 1994-08-08 | 1996-02-22 | Pharmacia S.P.A. | Distamycin a analogues as antitumour or antiviral agents |
US7049061B1 (en) | 1996-02-26 | 2006-05-23 | California Institute Of Technology | Stereochemical control of the DNA binding affinity, sequence specificity, and orientation-preference of chiral hairpin polyamides in the minor groove |
US6683189B1 (en) | 1996-02-26 | 2004-01-27 | California Institute Of Technology | Method for the synthesis of pyrrole and imidazole carboxamides on a solid support |
US6555692B1 (en) | 1996-02-26 | 2003-04-29 | California Institute Of Technology | Preparation and use of bifunctional molecules having DNA sequence binding specificity |
US6545162B1 (en) | 1996-02-26 | 2003-04-08 | California Institute Of Technology | Method for the synthesis of pyrrole and imidazole carboxamides on a solid support |
US6090947A (en) * | 1996-02-26 | 2000-07-18 | California Institute Of Technology | Method for the synthesis of pyrrole and imidazole carboxamides on a solid support |
US6506906B1 (en) | 1996-02-26 | 2003-01-14 | California Institute Of Technology | Preparation and use of bifunctional molecules having DNA sequence binding specificity |
US6472537B1 (en) | 1996-02-26 | 2002-10-29 | California Institute Of Technology | Polyamides for binding in the minor groove of double stranded DNA |
US6303312B1 (en) | 1996-07-31 | 2001-10-16 | California Institute Of Technology | Complex formation between dsDNA and oligomer of cyclic heterocycles |
US6143901A (en) * | 1996-07-31 | 2000-11-07 | Genesoft, Inc. | Complex formation between dsDNA and pyrrole imidazole polyamides |
US5998140A (en) * | 1996-07-31 | 1999-12-07 | The Scripps Research Institute | Complex formation between dsDNA and oligomer of cyclic heterocycles |
US6635417B1 (en) | 1996-07-31 | 2003-10-21 | California Institute Of Technology | Complex formation between DSDNA and oligomer of cyclic heterocycles |
US6153642A (en) * | 1996-11-11 | 2000-11-28 | Pharmacia & Upjohn S.P.A. | Benzoheterocyclic distamycin derivatives, process for preparing them, and their use as antitumor and antiviral agents |
WO1998021202A1 (en) * | 1996-11-11 | 1998-05-22 | Pharmacia & Upjohn S.P.A. | Benzoheterocyclic distamycin derivatives, process for preparing them, and their use as antitumor and antiviral agents |
US6458768B1 (en) | 1998-03-27 | 2002-10-01 | Pharmacia & Upjohn, S.P.A. | Benzoheterocyclic distamycin derivatives, process for preparing them, and their use as antitumor agents |
WO1999050266A1 (en) * | 1998-03-27 | 1999-10-07 | Pharmacia & Upjohn S.P.A. | Benzoheterocyclic distamycin derivatives, process for preparing them, and their use as antitumor agents |
WO2000006541A1 (en) * | 1998-07-30 | 2000-02-10 | Pharmacia & Upjohn S.P.A. | Sulfurated distamycin derivatives, process for preparing them, and their use as antitumor agents |
US6559125B1 (en) | 2000-01-28 | 2003-05-06 | California Institute Of Technology | Polyamide-alkylator conjugates and related products and method |
US6555693B2 (en) | 2000-03-16 | 2003-04-29 | Genesoft, Inc. | Charged compounds comprising a nucleic acid binding moiety and uses therefor |
US7301037B2 (en) | 2000-03-16 | 2007-11-27 | Genesoft, Inc. | Charged compounds comprising a nucleic acid binding moiety and uses therefor |
US7078536B2 (en) | 2001-03-14 | 2006-07-18 | Genesoft Pharmaceuticals, Inc. | Charged compounds comprising a nucleic acid binding moiety and uses therefor |
US7122626B2 (en) | 2001-04-26 | 2006-10-17 | Genesoft Pharmceuticals, Inc. | Halogen-substitued thienyl compounds |
US7498405B2 (en) | 2001-04-26 | 2009-03-03 | Genesoft Pharmaceuticals, Inc. | Halogen-substituted thienyl compounds |
US7348427B2 (en) | 2001-06-13 | 2008-03-25 | Genesoft Pharmaceuticals, Inc. | Antipathogenic benzamide compounds |
US7498349B2 (en) | 2002-08-02 | 2009-03-03 | Genesoft Pharmaceuticals, Inc. | Biaryl compounds having anti-infective activity |
US7265129B2 (en) | 2002-10-25 | 2007-09-04 | Genesoft Pharmaceuticals, Inc. | Anti-infective biaryl compounds |
US7129214B2 (en) | 2002-12-10 | 2006-10-31 | Oscient Pharmaceuticals Corporation | Antibacterial compounds having a (pyrrole carboxamide)-(benzamide)-(imidazole carboxamide) motif |
US7642245B2 (en) | 2002-12-10 | 2010-01-05 | Oscient Pharmaceuticals Corporation | Antibacterial compounds having a (pyrrole carboxamide)-(benzamide)-(imidazole carboxamide) motif |
Also Published As
Publication number | Publication date |
---|---|
EP0690840A1 (en) | 1996-01-10 |
ITFI930030A1 (it) | 1994-09-01 |
KR960701007A (ko) | 1996-02-24 |
JPH08508720A (ja) | 1996-09-17 |
IT1271456B (it) | 1997-05-28 |
ITFI930030A0 (it) | 1993-03-01 |
AU6206894A (en) | 1994-09-26 |
CA2157187A1 (en) | 1994-09-15 |
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