AR024600A1 - PREPARATION OF CYCLOPENTANE AND CYCLOPENTENE COMPOUNDS SUBSTITUTED AND CERTAIN INTERMEDIARIES - Google Patents
PREPARATION OF CYCLOPENTANE AND CYCLOPENTENE COMPOUNDS SUBSTITUTED AND CERTAIN INTERMEDIARIESInfo
- Publication number
- AR024600A1 AR024600A1 ARP000103274A ARP000103274A AR024600A1 AR 024600 A1 AR024600 A1 AR 024600A1 AR P000103274 A ARP000103274 A AR P000103274A AR P000103274 A ARP000103274 A AR P000103274A AR 024600 A1 AR024600 A1 AR 024600A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- substituted
- cyclopentane
- isoxazoline
- Prior art date
Links
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title abstract 6
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 title abstract 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical group C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- -1 cyclopentane compound Chemical class 0.000 abstract 4
- 150000002547 isoxazolines Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 150000001940 cyclopentanes Chemical class 0.000 abstract 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 101150009274 nhr-1 gene Proteins 0.000 abstract 2
- 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 abstract 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical compound [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 abstract 1
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 abstract 1
- 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 abstract 1
- 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 101150111293 cor-1 gene Proteins 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002433 cyclopentenyl group Chemical class C1(=CCCC1)* 0.000 abstract 1
- 229940042406 direct acting antivirals neuraminidase inhibitors Drugs 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000003971 isoxazolinyl group Chemical group 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 101150058824 queH gene Proteins 0.000 abstract 1
- 238000006268 reductive amination reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002911 sialidase inhibitor Substances 0.000 abstract 1
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/16—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Compuestos de ciclopentano y ciclopenteno sustituidos que son utiles como inhibidores de la neuraminidasa representados por las siguientes formulas (1) y(2), donde cada R1 es individualmente alquilo o alquilo sustituido, alquenilo o alquenilo sustituido de 1-6 átomos de carbono, o H; cada uno de R2 y R3 esindividualmente alquilo o alquenilo de 1-8 átomos de carbono, cicloalquilo o cicloalquilo sustituido de 4-8 átomos de carbono, arilo o arilo sustituido,arilalquilo o arilalquilo sustituido,o Hcon la condicion de que por lo menos uno de R2 y R3 sea otro que H;X es NHR1, NHC (=NH) NHR4 donde R4 es H, alquilo de1-6 átomos de carbono, OR1, COR1, COOR1, CN o NO2; A es H, F, OR1, OCOR1, -OOCNHR1, NHR1, o NHCOOR1; y sales aceptables para uso farmacéutico de los mismos. Esposible preparar los compuestos de formula (1) donde A es H a partir de derivados de isoxazolina novedosos representados por la formula (3), donde R2 y R3tienen los valores definidos anteriormente y donde cada uno de Y y Zes individualmente COOR1 o H con la condicion de que por lo menos uno de Y y Z sea otro queH. Los derivados de isoxazolina de acuerdo con la formula (3) se preparan de acuerdo con el siguiente procedimiento: Se hace reaccionar a un oxido de nitrilodela formula (4) con ciertos derivados de ciclopentano. Se puede preparar el compuesto ciclopentano de formula (1) a partir de los derivados de isoxazolina utsupra reduciendo los derivados de isoxazolina de formula (3) para formar un derivado aminoalcohol. Se hace reaccionar el compuesto aminoalcohol de formula (5)con un anhídrido o haluro ácido de un ácido carboxílico para dar un compuesto acilado. Después, el grupo alcohol del compuesto acilado se convierte en gruposaliente que a su vez es desplazado por amoníaco o guanidina para dar compuestos de formula (1) o se desplaza al grupo saliente con un ion azida que a su vezse convierte en la guanidina usando un compuesto NH2. En un proceso alternativo para preperar el compuesto ciclopentano deformula (1), se convierte en cetonaun compuesto isoxazolina de formula (3) abriendo su anillo isoxazolina Se somete a la cetona a una aminacion reductiva de la conversion al producto final comoSubstituted cyclopentane and cyclopentene compounds that are useful as neuraminidase inhibitors represented by the following formulas (1) and (2), where each R1 is individually substituted alkyl or alkyl, alkenyl or substituted alkenyl of 1-6 carbon atoms, or H; each of R2 and R3 is individually alkyl or alkenyl of 1-8 carbon atoms, cycloalkyl or substituted cycloalkyl of 4-8 carbon atoms, aryl or substituted aryl, arylalkyl or substituted arylalkyl, or H with the proviso that at least one of R2 and R3 is other than H; X is NHR1, NHC (= NH) NHR4 where R4 is H, alkyl of 1-6 carbon atoms, OR1, COR1, COOR1, CN or NO2; A is H, F, OR1, OCOR1, -OOCNHR1, NHR1, or NHCOOR1; and salts acceptable for pharmaceutical use thereof. It is possible to prepare the compounds of formula (1) where A is H from novel isoxazoline derivatives represented by formula (3), where R2 and R3 have the values defined above and where each of Y and Z individually COOR1 or H with the condition that at least one of Y and Z is another queH. The isoxazoline derivatives according to the formula (3) are prepared according to the following procedure: The nitrile oxide formula (4) is reacted with certain cyclopentane derivatives. The cyclopentane compound of formula (1) can be prepared from the isoxazoline derivatives utsupra by reducing the isoxazoline derivatives of formula (3) to form an amino alcohol derivative. The amino alcohol compound of formula (5) is reacted with an acid anhydride or halide of a carboxylic acid to give an acylated compound. Then, the alcohol group of the acylated compound is converted into a salient group which in turn is displaced by ammonia or guanidine to give compounds of formula (1) or is displaced to the leaving group with an azide ion which in turn is converted into guanidine using a NH2 compound. In an alternative process to prepare the cyclopentane deformula compound (1), it is converted into ketone or an isoxazoline compound of formula (3) by opening its isoxazoline ring. The ketone is subjected to a reductive amination of the conversion to the final product as
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14084099P | 1999-06-28 | 1999-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR024600A1 true AR024600A1 (en) | 2002-10-16 |
Family
ID=22493015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP000103274A AR024600A1 (en) | 1999-06-28 | 2000-06-28 | PREPARATION OF CYCLOPENTANE AND CYCLOPENTENE COMPOUNDS SUBSTITUTED AND CERTAIN INTERMEDIARIES |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1189862A1 (en) |
| JP (1) | JP2003530306A (en) |
| AR (1) | AR024600A1 (en) |
| AU (1) | AU6056600A (en) |
| CA (1) | CA2377287A1 (en) |
| WO (1) | WO2001000558A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001062242A1 (en) * | 2000-02-24 | 2001-08-30 | Biocryst Pharmaceuticals, Inc. | Prodrugs of substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors |
| WO2002092555A1 (en) * | 2001-05-11 | 2002-11-21 | Sankyo Company, Limited | Sialic acid derivatives |
| CN101367750B (en) * | 2007-08-14 | 2012-05-23 | 中国人民解放军军事医学科学院毒物药物研究所 | (1S,2S,3S,4R)-3-[(1S)-1-acet-ammonia-2-ethyl-butyl]-4- guanidino-2-hydroxyl-cyclopentyl-1-carboxylic acid aqua compound and medical uses thereof |
| CN102584637B (en) * | 2011-01-17 | 2014-07-09 | 天津药物研究院 | Peramivir hydrate crystal, preparation method, medical compound and usage thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR016162A1 (en) * | 1997-12-17 | 2001-06-20 | Biocryst Pharm Inc | SUBSTITUTED CYCLOPENTANE AND CYCLOPENTENE COMPOUNDS THAT ARE USEFUL AS INHIBITORS OF NEURAMINIDASE AND COMPOSITION THAT CONTAINS THEM. |
-
2000
- 2000-06-28 AR ARP000103274A patent/AR024600A1/en unknown
- 2000-06-28 AU AU60566/00A patent/AU6056600A/en not_active Abandoned
- 2000-06-28 CA CA002377287A patent/CA2377287A1/en not_active Abandoned
- 2000-06-28 WO PCT/US2000/017685 patent/WO2001000558A1/en not_active Ceased
- 2000-06-28 JP JP2001506972A patent/JP2003530306A/en active Pending
- 2000-06-28 EP EP00946871A patent/EP1189862A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001000558A1 (en) | 2001-01-04 |
| JP2003530306A (en) | 2003-10-14 |
| EP1189862A1 (en) | 2002-03-27 |
| CA2377287A1 (en) | 2001-01-04 |
| AU6056600A (en) | 2001-01-31 |
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