SK5642000A3 - CRYSTALLINE POLYMORPHIC FORM OF 1,3-DICYCLOPROPYLMETHYL-8-AMINOì (54) XANTHINE, PROCESS FOR ITS PRODUCTION, PHARMACEUTICALì - Google Patents
CRYSTALLINE POLYMORPHIC FORM OF 1,3-DICYCLOPROPYLMETHYL-8-AMINOì (54) XANTHINE, PROCESS FOR ITS PRODUCTION, PHARMACEUTICALì Download PDFInfo
- Publication number
- SK5642000A3 SK5642000A3 SK564-2000A SK5642000A SK5642000A3 SK 5642000 A3 SK5642000 A3 SK 5642000A3 SK 5642000 A SK5642000 A SK 5642000A SK 5642000 A3 SK5642000 A3 SK 5642000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- dicyclopropylmethyl
- polymorphic form
- xanthine
- amino
- crystalline polymorphic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- 230000008569 process Effects 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 229940075420 xanthine Drugs 0.000 title claims description 3
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title claims 4
- KSPYMJJKQMWWNB-UHFFFAOYSA-N cipamfylline Chemical compound O=C1N(CC2CC2)C(=O)C=2NC(N)=NC=2N1CC1CC1 KSPYMJJKQMWWNB-UHFFFAOYSA-N 0.000 claims abstract description 35
- 238000011282 treatment Methods 0.000 claims abstract description 22
- 201000010099 disease Diseases 0.000 claims abstract description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
- 230000001404 mediated effect Effects 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims abstract 3
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims abstract 3
- 239000013078 crystal Substances 0.000 claims description 87
- 238000001816 cooling Methods 0.000 claims description 39
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 23
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 12
- 238000001237 Raman spectrum Methods 0.000 claims description 12
- 238000010521 absorption reaction Methods 0.000 claims description 11
- 238000000862 absorption spectrum Methods 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- 238000002441 X-ray diffraction Methods 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 230000003247 decreasing effect Effects 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 229950002405 cipamfylline Drugs 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 229910052739 hydrogen Inorganic materials 0.000 description 25
- 239000001257 hydrogen Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- 238000001228 spectrum Methods 0.000 description 25
- 125000004429 atom Chemical group 0.000 description 22
- 210000004027 cell Anatomy 0.000 description 22
- 238000002474 experimental method Methods 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 230000003993 interaction Effects 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- 238000002329 infrared spectrum Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 230000009102 absorption Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000010583 slow cooling Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000004566 IR spectroscopy Methods 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 229910002804 graphite Inorganic materials 0.000 description 6
- 239000010439 graphite Substances 0.000 description 6
- 238000002372 labelling Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 238000012937 correction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000002424 x-ray crystallography Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 101100438156 Arabidopsis thaliana CAD7 gene Proteins 0.000 description 3
- 101150071647 CAD4 gene Proteins 0.000 description 3
- 101100322652 Catharanthus roseus ADH13 gene Proteins 0.000 description 3
- 101100087088 Catharanthus roseus Redox1 gene Proteins 0.000 description 3
- 238000000958 atom scattering Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910003460 diamond Inorganic materials 0.000 description 3
- 239000010432 diamond Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- 239000000852 hydrogen donor Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 101100508413 Caenorhabditis elegans ifc-1 gene Proteins 0.000 description 1
- 238000005079 FT-Raman Methods 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 229920003350 Spectratech® Polymers 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 210000000270 basal cell Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- -1 cyclopropyl methylene Chemical group 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000005489 elastic deformation Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003696 structure analysis method Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000012982 x-ray structure analysis Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
-
- 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
- A61P37/08—Antiallergic agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6323897P | 1997-10-23 | 1997-10-23 | |
| PCT/US1998/022451 WO1999020625A1 (en) | 1997-10-23 | 1998-10-23 | Novel polymorphic forms of cipamfylline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK5642000A3 true SK5642000A3 (en) | 2000-09-12 |
Family
ID=22047900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK564-2000A SK5642000A3 (en) | 1997-10-23 | 1998-10-23 | CRYSTALLINE POLYMORPHIC FORM OF 1,3-DICYCLOPROPYLMETHYL-8-AMINOì (54) XANTHINE, PROCESS FOR ITS PRODUCTION, PHARMACEUTICALì |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US6583283B1 (id) |
| EP (1) | EP1025103A4 (id) |
| JP (1) | JP2001520228A (id) |
| KR (1) | KR20010031246A (id) |
| CN (1) | CN1280579A (id) |
| AP (1) | AP2000001793A0 (id) |
| AR (1) | AR015190A1 (id) |
| AU (1) | AU751561B2 (id) |
| BG (1) | BG104368A (id) |
| BR (1) | BR9814099A (id) |
| CA (1) | CA2306980A1 (id) |
| CO (1) | CO4990930A1 (id) |
| DZ (1) | DZ2629A1 (id) |
| EA (1) | EA003445B1 (id) |
| HU (1) | HUP0100019A3 (id) |
| ID (1) | ID23885A (id) |
| IL (1) | IL135711A0 (id) |
| MA (1) | MA24682A1 (id) |
| NO (1) | NO20002012L (id) |
| NZ (1) | NZ504051A (id) |
| PE (1) | PE122599A1 (id) |
| PL (1) | PL340257A1 (id) |
| SA (1) | SA99191117A (id) |
| SK (1) | SK5642000A3 (id) |
| TR (1) | TR200001109T2 (id) |
| UY (2) | UY25220A1 (id) |
| WO (1) | WO1999020625A1 (id) |
| ZA (1) | ZA989622B (id) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL364135A1 (en) | 2001-01-31 | 2004-12-13 | Pfizer Products Inc. | Nicotinamide biaryl derivatives useful as inhibitors of pde4 isozymes |
| BR0116850A (pt) | 2001-01-31 | 2004-02-25 | Pfizer Prod Inc | Derivados de amida de ácido tiazolil-, oxazolil-, pirrolil- e imidazolil- úteis como inibidores de isoenzimas de pde4 |
| CN1527830A (zh) | 2001-01-31 | 2004-09-08 | �Ʒ� | 用作pde4同工酶的抑制剂的醚衍生物 |
| US7250518B2 (en) | 2001-01-31 | 2007-07-31 | Pfizer Inc. | Nicotinamide acids, amides, and their mimetics active as inhibitors of PDE4 isozymes |
| AR040233A1 (es) | 2002-05-31 | 2005-03-23 | Schering Corp | Polimorfos inhibidores de xantina fosfodiesterasa v |
| CA2565965A1 (en) | 2004-05-06 | 2006-07-27 | Plexxikon, Inc. | Pde4b inhibitors and uses therefor |
| EP1786813A2 (en) | 2004-09-03 | 2007-05-23 | Plexxikon, Inc. | Bicyclic heteroaryl pde4b inhibitors |
| US7435818B2 (en) * | 2005-09-20 | 2008-10-14 | Scinopharm Taiwan, Ltd. | Crystal forms of irinotecan hydrochloride |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8906792D0 (en) | 1989-03-23 | 1989-05-10 | Beecham Wuelfing Gmbh & Co Kg | Treatment and compounds |
| GB9020921D0 (en) * | 1990-09-26 | 1990-11-07 | Beecham Group Plc | Novel compounds |
| GB9020959D0 (en) * | 1990-09-26 | 1990-11-07 | Beecham Group Plc | Novel compounds |
-
1998
- 1998-10-21 DZ DZ980239A patent/DZ2629A1/xx active
- 1998-10-21 MA MA25309A patent/MA24682A1/fr unknown
- 1998-10-21 AR ARP980105252A patent/AR015190A1/es not_active Application Discontinuation
- 1998-10-22 ZA ZA989622A patent/ZA989622B/xx unknown
- 1998-10-23 AU AU12744/99A patent/AU751561B2/en not_active Ceased
- 1998-10-23 TR TR2000/01109T patent/TR200001109T2/xx unknown
- 1998-10-23 BR BR9814099-0A patent/BR9814099A/pt not_active IP Right Cessation
- 1998-10-23 US US09/529,865 patent/US6583283B1/en not_active Expired - Fee Related
- 1998-10-23 HU HU0100019A patent/HUP0100019A3/hu unknown
- 1998-10-23 EP EP98956156A patent/EP1025103A4/en not_active Withdrawn
- 1998-10-23 EA EA200000448A patent/EA003445B1/ru not_active IP Right Cessation
- 1998-10-23 CO CO98061838A patent/CO4990930A1/es unknown
- 1998-10-23 UY UY25220A patent/UY25220A1/es not_active Application Discontinuation
- 1998-10-23 PL PL98340257A patent/PL340257A1/xx unknown
- 1998-10-23 ID IDW20000714A patent/ID23885A/id unknown
- 1998-10-23 PE PE1998001002A patent/PE122599A1/es not_active Application Discontinuation
- 1998-10-23 KR KR1020007004228A patent/KR20010031246A/ko not_active Ceased
- 1998-10-23 CN CN98810380A patent/CN1280579A/zh active Pending
- 1998-10-23 IL IL13571198A patent/IL135711A0/xx unknown
- 1998-10-23 SK SK564-2000A patent/SK5642000A3/sk unknown
- 1998-10-23 WO PCT/US1998/022451 patent/WO1999020625A1/en not_active Ceased
- 1998-10-23 JP JP2000516967A patent/JP2001520228A/ja not_active Withdrawn
- 1998-10-23 CA CA002306980A patent/CA2306980A1/en not_active Abandoned
- 1998-10-23 AP APAP/P/2000/001793A patent/AP2000001793A0/en unknown
- 1998-10-23 NZ NZ504051A patent/NZ504051A/xx unknown
-
1999
- 1999-02-04 UY UY25380A patent/UY25380A1/es not_active IP Right Cessation
- 1999-02-27 SA SA99191117A patent/SA99191117A/ar unknown
-
2000
- 2000-04-17 NO NO20002012A patent/NO20002012L/no not_active Application Discontinuation
- 2000-04-21 BG BG104368A patent/BG104368A/xx unknown
-
2002
- 2002-04-18 US US10/125,754 patent/US20020173648A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EA200000448A1 (ru) | 2000-10-30 |
| UY25380A1 (es) | 1999-11-17 |
| HUP0100019A2 (hu) | 2002-01-28 |
| ZA989622B (en) | 1999-04-23 |
| AP2000001793A0 (en) | 2000-06-30 |
| SA99191117A (ar) | 2005-12-03 |
| CO4990930A1 (es) | 2000-12-26 |
| AU1274499A (en) | 1999-05-10 |
| PE122599A1 (es) | 2000-02-12 |
| TR200001109T2 (tr) | 2000-09-21 |
| DZ2629A1 (fr) | 2003-03-08 |
| AR015190A1 (es) | 2001-04-18 |
| NO20002012D0 (no) | 2000-04-17 |
| CN1280579A (zh) | 2001-01-17 |
| CA2306980A1 (en) | 1999-04-29 |
| JP2001520228A (ja) | 2001-10-30 |
| HUP0100019A3 (en) | 2003-01-28 |
| BR9814099A (pt) | 2000-10-10 |
| WO1999020625A1 (en) | 1999-04-29 |
| NO20002012L (no) | 2000-04-17 |
| AU751561B2 (en) | 2002-08-22 |
| EP1025103A4 (en) | 2001-11-14 |
| NZ504051A (en) | 2003-02-28 |
| BG104368A (en) | 2001-02-28 |
| MA24682A1 (fr) | 1999-07-01 |
| KR20010031246A (ko) | 2001-04-16 |
| IL135711A0 (en) | 2001-05-20 |
| US6583283B1 (en) | 2003-06-24 |
| US20020173648A1 (en) | 2002-11-21 |
| UY25220A1 (es) | 2001-08-27 |
| ID23885A (id) | 2000-05-25 |
| EP1025103A1 (en) | 2000-08-09 |
| PL340257A1 (en) | 2001-01-29 |
| EA003445B1 (ru) | 2003-06-26 |
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