WO2002079137A8 - Interleukin-1 and tumor necrosis factor-alpha modulators and their enantiomers, their synthesis and use - Google Patents
Interleukin-1 and tumor necrosis factor-alpha modulators and their enantiomers, their synthesis and useInfo
- Publication number
- WO2002079137A8 WO2002079137A8 PCT/US2002/009591 US0209591W WO02079137A8 WO 2002079137 A8 WO2002079137 A8 WO 2002079137A8 US 0209591 W US0209591 W US 0209591W WO 02079137 A8 WO02079137 A8 WO 02079137A8
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- hydrogen
- alkenyl
- halogen
- alkyls
- Prior art date
Links
- 102000000589 Interleukin-1 Human genes 0.000 title abstract 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title 1
- 108010082786 Interleukin-1alpha Proteins 0.000 title 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 title 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000002431 hydrogen Chemical group 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 8
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 150000002367 halogens Chemical class 0.000 abstract 6
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 6
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 abstract 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 4
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001266 acyl halides Chemical class 0.000 abstract 2
- 239000002246 antineoplastic agent Substances 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000000651 prodrug Substances 0.000 abstract 2
- 229940002612 prodrug Drugs 0.000 abstract 2
- 150000003511 tertiary amides Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 108010002352 Interleukin-1 Proteins 0.000 abstract 1
- 206010054094 Tumour necrosis Diseases 0.000 abstract 1
- 208000036142 Viral infection Diseases 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000001093 anti-cancer Effects 0.000 abstract 1
- 150000003950 cyclic amides Chemical class 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 208000026278 immune system disease Diseases 0.000 abstract 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003334 secondary amides Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 1
- 238000010189 synthetic method Methods 0.000 abstract 1
- 230000009385 viral infection Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/58—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/05—Alcohols containing rings other than six-membered aromatic rings
- C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/35—Unsaturated compounds having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Novel compounds are disclosed that have specific chemical structures, and prodrug esters and acid-addition salts thereof, that are useful as Interleukin-1 and Tumor Necrosis Factor-a modulators, and thus are useful in the treatment of various diseases. Wherein the R groups are defined as follows: if any R3-R5, R7, R8, R11-R13 is not hydrogen, R2 or R6 or R9 is not methyl, or R10 is not CH2, then R1 is selected from the group consisting of hydrogen, a halogen, COOH, C1-C12 carboxylic acids, C1-C12 acyl halides, C1-C12 acyl residues, C1-C12 esters, C1-C12 secondary amides, (C1-C12)(C1-C12) tertiary amides, (C1-C12)(C1-C12) cyclic amides, (C1-C12) amines, C1-C12 alcohols, (C1-C12)(C1-C12) ethers, C1-C12 alkyls, C1-C12 substituted alkyls, C2-C12 alkenyls, C2-C12 substituted alkenyls, and C5-C12 aryls. If all R3-R5, R7, R8, R11-R13 are hydrogen, R2, R6, and R9 are each methyl, and R10 is CH2, then R1 is selected from hydrogen, a halogen, C1-C12 carboxylic acids, C1-C12 acyl halides, C1-C12 acyl residues, C2-C12 esters, C2-C12 secondary amides, (C1-C12)(C1-C12) tertiary amides, C2-C12 alcohols, (C1-C12)(C1-C12) ethers other than methyl-acetyl ether, C2-C12 alkyls, C1-C12 substituted alkyls, C2-C12 alkenyls, C2-C12 substituted alkenyls, and C2-C12 aryls. R2 and R9 are each separately selected from hydrogen, a halogen, C1-C12 alkyl, C1-C12 substituted alkyls, C2-C12 alkenyl, C2-C12 substituted alkenyl, C2 - C12 alkynyl, C1-C12 acyl, C1-C12 alcohol, and C5-C12 aryl. R3-R5, R7, R8, and R11-R13 are each separately selected from hydrogen, a halogen, C1-C12 alkyl, C1-C12 substituted alkyls, C2-C12 alkenyl, C2-C12 substituted alkenyl, C2-C12 alkynyl, and C5-C12 aryl. R6 is selected from hydrogen, a halogen, C1-C12 alkyl, C1-C12 substituted alkyls, C2-C12 alkenyl, C2-C12 substituted alkenyl, and C2-C12 alkynyl. R10 is selected from hydrogen, a halogen, CH2, C1-C6 alkyl, C1-C6 substituted alkyl, C2-C6 alkenyl, C2-C6 substituted alkenyl, C1-C12 alcohol, and C5-C12 aryl. Pharmaceutical compositions comprising, and uses of, therapeutically effective amounts of the aove compounds and their prodrug esters, and a pharmaceutically acceptable carrier, are also disclosed, and are useful as, for example, anti-inflammatory analgesics, in treating immune disorders, as anti-cancer and anti-tumor agents, and in the treatment of cardiovascular disease, skin redness, and viral infection. Completely synthetic and semi-synthetic methods of making these compounds and their analogs, are also disclosed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2002255963A AU2002255963A1 (en) | 2001-03-28 | 2002-03-27 | Interleukin-1 and tumor necrosis factor-alpha modulators and their enantiomers, their synthesis and use |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27938101P | 2001-03-28 | 2001-03-28 | |
| US60/279,381 | 2001-03-28 | ||
| US27995201P | 2001-03-29 | 2001-03-29 | |
| US60/279,952 | 2001-03-29 | ||
| US33203101P | 2001-11-21 | 2001-11-21 | |
| US60/332,031 | 2001-11-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO2002079137A1 WO2002079137A1 (en) | 2002-10-10 |
| WO2002079137A8 true WO2002079137A8 (en) | 2002-11-07 |
| WO2002079137A9 WO2002079137A9 (en) | 2004-05-27 |
Family
ID=27403065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2002/009591 WO2002079137A1 (en) | 2001-03-28 | 2002-03-27 | Interleukin-1 and tumor necrosis factor-alpha modulators and their enantiomers, their synthesis and use |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU2002255963A1 (en) |
| WO (1) | WO2002079137A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1178952T5 (en) | 1999-05-14 | 2008-03-17 | Univ California | New Modulators of Interleukin 1 and Tumor Necrosis Factor α, Synthesis of Said Modulators and Methods of Using Said Modulators |
| US7893299B2 (en) * | 2005-07-21 | 2011-02-22 | Nereus Pharmaceuticals, Inc. | Interleukin-1 and tumor necrosis factor-αmodulators; syntheses of such modulators and methods of using such modulators |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0145941B1 (en) * | 1994-06-13 | 1998-08-17 | 김은영 | Pharmaceutical composition comprising interleukin-1 and acantosan useful for inhibiting production of tumor necrosis factor-alpha |
| DE69913497T2 (en) * | 1998-01-26 | 2004-09-16 | Sae Han Pharm. Co., Ltd. | DITERPENDER DERIVATIVES AND ANTI-INFLAMMATORY PAINTS THAT CONTAIN THEM |
| DK1178952T5 (en) * | 1999-05-14 | 2008-03-17 | Univ California | New Modulators of Interleukin 1 and Tumor Necrosis Factor α, Synthesis of Said Modulators and Methods of Using Said Modulators |
-
2002
- 2002-03-27 WO PCT/US2002/009591 patent/WO2002079137A1/en not_active Application Discontinuation
- 2002-03-27 AU AU2002255963A patent/AU2002255963A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002079137A1 (en) | 2002-10-10 |
| AU2002255963A1 (en) | 2002-10-15 |
| WO2002079137A9 (en) | 2004-05-27 |
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