AR031844A1 - Resolucion enzimatica de moduladores selectivos de receptores de estrogenos - Google Patents
Resolucion enzimatica de moduladores selectivos de receptores de estrogenosInfo
- Publication number
- AR031844A1 AR031844A1 ARP010102123A ARP010102123A AR031844A1 AR 031844 A1 AR031844 A1 AR 031844A1 AR P010102123 A ARP010102123 A AR P010102123A AR P010102123 A ARP010102123 A AR P010102123A AR 031844 A1 AR031844 A1 AR 031844A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- optionally substituted
- independently selected
- ring
- substituents independently
- Prior art date
Links
- 230000002255 enzymatic effect Effects 0.000 title 1
- 125000001424 substituent group Chemical group 0.000 abstract 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 102000004190 Enzymes Human genes 0.000 abstract 2
- 108090000790 Enzymes Proteins 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000002837 carbocyclic group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 102000004882 Lipase Human genes 0.000 abstract 1
- 108090001060 Lipase Proteins 0.000 abstract 1
- 239000004367 Lipase Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 239000012062 aqueous buffer Substances 0.000 abstract 1
- -1 bicyclic amine Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000006196 deacetylation Effects 0.000 abstract 1
- 238000003381 deacetylation reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 235000019421 lipase Nutrition 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/16—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing two or more hetero rings
- C12P17/165—Heterorings having nitrogen atoms as the only ring heteroatoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
- C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero ring
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/16—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing two or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y301/00—Hydrolases acting on ester bonds (3.1)
- C12Y301/01—Carboxylic ester hydrolases (3.1.1)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y301/00—Hydrolases acting on ester bonds (3.1)
- C12Y301/01—Carboxylic ester hydrolases (3.1.1)
- C12Y301/01013—Sterol esterase (3.1.1.13)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Physical Education & Sports Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Analytical Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Un procedimiento para la preparacion de un compuesto de formula 1 en la que A se selecciona de CH2 y NR; B, D y E se seleccionan independientemente de CH y N; Y es (a) fenilo, opcionalmente sustituido con 1-3 sustituyentes seleccionados independientemente de R4; (b) naftilo, opcionalmente sustituido con 1-3 sustituyentes seleccionados independientemente de R4; (c) cicloalquilo (C3-8), opcionalmente sustituido con 1-2 sustituyentes seleccionados independientemente de R4; (d) cicloalquinilo (C3-8), opcionalmente sustituido con 1-2 sustituyentes seleccionados independientemente de R4; (e) un heterociclo de cinco miembros que contiene hasta dos heteroátomos seleccionados del grupo constituido por -O-, -NR2- y -S(O)n-, opcionalmente sustituido con 1-3 sustituyentes seleccionados independientemente de R4, (f) un heterociclo de seis miembros que contiene hasta dos heteroátomos seleccionados del grupo constituido por -O-, -NR2- y -S(O)n-, opcionalmente sustituido con 1-3 sustituyentes seleccionados independientemente de R4; o (g) un sistema de anillo bicíclico constituido por un anillo heterocíclico de cinco a seis miembros condensado con un anillo fenilo, conteniendo el citado anillo heterocíclico hasta dos heteroátomos seleccionados del grupo constituido por -O-, -NR2-, NR2- y -S(O)n-, opcionalmente sustituido con 1-3 sustituyentes seleccionados independientemente de R4; Z1 es (a) -(CH2)pW(CH2)q-; (b) -O(CH2)pCR5R6-; (c)-O(CH2)pW(CH2)q; (d) -OCHR2CHR3-; o (e)-SCHR2CHR3-; G es (a) -NR7R8; (b) formula (2) en la que n es 0, 1 o 2; m es 1, 2 o 3; Z2 es -NH-, -O-, -S-, o -CH2-; opcionalmente condensado sobre átomos de carbono adyacentes con uno o dos anillos fenilo y sustituido opcional e independientemente sobre carbono con uno a tres sustituyentes y opcional e independientemente, sobre nitrogeno con un sustituyente químicamente adecuado seleccionado de R4; o (c) una amina bicíclica que contiene de cinco a doce átomos de carbono, que forma un puente o está condensada, y opcionalmente sustituida con 1-3 sustituyentes seleccionados independientemente de R4; Z1 y G combinados pueden ser formula (3); W es (a) -CH2-; (b) -CH=CH-; (c) -O-; (d) -O-; (d) -NR2-; (e) -S(O)n-; (f) >C=O, (g) -CR2(OH)-; (h) -CONR2-; (i) -NR2CO-; (j) formula (4) o (k) ûCsC-; R es hidrogeno o alquilo (C1-6); R2 y R3 son independientemente (a) hidrogeno; o (b) alquilo (C1-4); R4 es (a) hidrogeno; (b) halogeno; (c) alquilo (C1-6); (d) alcoxi (C1-4); (e) aciloxi (C1-4); (f) alquiltio (C1-4); (g) alquilsulfinilo (C1-4); (h) alquilsulfonilo (C1-4); (i) hidroxialquilo (C1-4); (j) arilalquilo (C1-4); (k) -CO2H; (l) -CN; (m) -CONHOR; (n) -SO2NHR; (o) -NH2; (p) alquil (C1-4) amino; (q) dialquil (C1-4) amino; (r) -NHSO2R; (s) -NO2; (t) -arilo; o (u) -OH: R5 y R6 son independientemente alquilo (C1-8) o forman conjuntamente un anillo carbocíclico C3-10; R7 y R8 son independientemente (a) fenilo; (b) un anillo carbocíclico (C3-10) saturado o insaturado (c) un anillo heterocíclico (C3-10) que contiene hasta dos heteroátomos, seleccionados de O-, -N- y -S-; (d) H, (e) alquilo C1-6; o (f) forman un anillo de 3 a 8 miembros que contienen nitrogeno con R5 o R6; R7 y R8 en forma lineal o de anillo pueden estar opcionalmente sustituidos con hasta tres sustituyentes seleccionados independientemente de alquilo (C1-6), halogeno, alcoxi, hidroxi, y carboxi; el anillo formado por R7 y R8 puede estar opcionalmente condensado con un anillo fenilo; ( )e y ( )n son (CH2)e y (CH2)n respectivamente; e es 0, 1 o 2;; m es 1, 2 o 3; n es 0, 1 o 2; p es 0, 1, 2, o 3; q es 0, 1 , 2 o 3; y los isomeros opticos y geométricos de éste; caracterizado porque comprende la desacetilacion selectiva de un compuesto de formula (5) en la que R1 es alquilo (C1-6), alquenilo (C2-6), alquinilo (C2-6), estando los grupos alquilo, alquenilo o alquinilo (C2-6) opcionalmente sustituidos con uno a tres halo, en presencia de una enzima hidrolítica y una solucion tampon acuosa. un procedimiento caracterizado porque la enzima hidrolítica es una lipasa.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20241800P | 2000-05-08 | 2000-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR031844A1 true AR031844A1 (es) | 2003-10-08 |
Family
ID=22749787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP010102123A AR031844A1 (es) | 2000-05-08 | 2001-05-04 | Resolucion enzimatica de moduladores selectivos de receptores de estrogenos |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US6828134B2 (es) |
| EP (1) | EP1156120B1 (es) |
| JP (1) | JP2002000293A (es) |
| KR (1) | KR100488385B1 (es) |
| CN (1) | CN1322842A (es) |
| AR (1) | AR031844A1 (es) |
| AT (1) | ATE346159T1 (es) |
| AU (1) | AU782597B2 (es) |
| BR (1) | BR0101802A (es) |
| CA (1) | CA2346426C (es) |
| CZ (1) | CZ20011576A3 (es) |
| DE (1) | DE60124616T2 (es) |
| ES (1) | ES2274854T3 (es) |
| HK (1) | HK1040264A1 (es) |
| HU (1) | HUP0101874A3 (es) |
| ID (1) | ID30106A (es) |
| IL (2) | IL168341A (es) |
| MX (1) | MXPA01004626A (es) |
| PL (1) | PL347407A1 (es) |
| RU (1) | RU2213778C2 (es) |
| SG (1) | SG100688A1 (es) |
| TW (1) | TWI237059B (es) |
| YU (1) | YU31101A (es) |
| ZA (1) | ZA200103666B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8853423B2 (en) | 2010-06-17 | 2014-10-07 | Seragon Pharmaceuticals, Inc. | Indane estrogen receptor modulators and uses thereof |
| CN109750013B (zh) * | 2019-03-27 | 2023-01-13 | 云南师范大学 | 一种脂肪酶突变体及其制备方法和应用 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4814282A (en) * | 1984-05-03 | 1989-03-21 | Abbott Laboratories | Centrifuge for two-dimensional centrifugation |
| DE3638762A1 (de) | 1986-11-13 | 1988-05-26 | Schering Ag | Racematspaltung von 7(alpha)-acyloxy-6ss-hydroxy-methyl-2-oxabicyclo (3.3.0)octan-3-onen durch stereospezifische enzymatische acylat-hydrolyse |
| US5248609A (en) * | 1986-11-13 | 1993-09-28 | Schering Aktiengesellschaft | Racemic separation of 7α-acyloxy-6β-hydroxymethyl-2-oxabicyclo[3.]-octan-3-ones by stereospecific enzymatic acylate hydrolysis |
| CA1319144C (en) * | 1986-11-14 | 1993-06-15 | Quirico Branca | Tetrahydronaphthalene derivatives |
| US5106750A (en) * | 1988-08-30 | 1992-04-21 | G. D. Searle & Co. | Enantio- and regioselective synthesis of organic compounds using enol esters as irreversible transacylation reagents |
| WO1991007501A1 (en) * | 1989-11-13 | 1991-05-30 | Pfizer Inc. | Enzymatic resolution of endo-bicyclo[2.2.1]heptan-2-ol and derived pharmaceutical agents |
| TW383306B (en) * | 1992-12-22 | 2000-03-01 | Lilly Co Eli | New use of 2-phenyl-3-aroylbenzothiophenes in lowering serum cholesterol |
| GB9304256D0 (en) * | 1993-03-03 | 1993-04-21 | Chiros Ltd | Arylalkanoic acid resolution |
| FR2724184B1 (fr) * | 1994-09-05 | 1997-01-03 | Rhone Poulenc Chimie | Procede de resolution d'un melange d'alcools stereoisomeres |
| US5589482A (en) * | 1994-12-14 | 1996-12-31 | Pfizer Inc. | Benzo-thiophene estrogen agonists to treat prostatic hyperplasia |
| US5552412A (en) * | 1995-01-09 | 1996-09-03 | Pfizer Inc | 5-substitued-6-cyclic-5,6,7,8-tetrahydronaphthalen2-ol compounds which are useful for treating osteoporosis |
| UA51676C2 (uk) | 1995-11-02 | 2002-12-16 | Пфайзер Інк. | (-)цис-6(s)-феніл-5(r)[4-(2-піролідин-1-ілетокси)феніл]-5,6,7,8-тетрагідронафталін-2-ол d-тартрат, спосіб його одержання, спосіб лікування захворювань, що піддаються лікуванню агоністами естрогену, та фармацевтична композиція |
| IL120266A (en) * | 1996-02-28 | 2005-05-17 | Pfizer | Use of estrogen antagonists and estrogen agonists in the preparation of medicaments for inhibiting pathological conditions |
| AU8058398A (en) * | 1997-06-17 | 1999-01-04 | Schering Corporation | Enzymatic kinetic resolution of an intermediate useful for preparing substitutedtricyclics |
| ATE265853T1 (de) * | 1998-06-16 | 2004-05-15 | Pfizer Prod Inc | Kombinationstherapeutika, enthaltend einen selektiven östrogenrezeptormodulator und prostaglandin e2 |
| PA8475901A1 (es) | 1998-06-16 | 2000-05-24 | Pfizer Prod Inc | Terapia de combinacion para la fragilidad musculoesqueletica |
| ID23459A (id) | 1998-08-28 | 2000-04-27 | Pfizer Prod Inc | Biotransformasi mikroba |
| US6180375B1 (en) | 1999-08-27 | 2001-01-30 | Pfizer Inc. | Microbial biotransformation |
-
2001
- 2001-04-19 ES ES01303554T patent/ES2274854T3/es not_active Expired - Lifetime
- 2001-04-19 DE DE60124616T patent/DE60124616T2/de not_active Expired - Fee Related
- 2001-04-19 EP EP01303554A patent/EP1156120B1/en not_active Expired - Lifetime
- 2001-04-19 AT AT01303554T patent/ATE346159T1/de not_active IP Right Cessation
- 2001-04-26 YU YU31101A patent/YU31101A/sh unknown
- 2001-04-26 CN CN01117132A patent/CN1322842A/zh active Pending
- 2001-04-30 IL IL168341A patent/IL168341A/en not_active IP Right Cessation
- 2001-04-30 IL IL142881A patent/IL142881A/en not_active IP Right Cessation
- 2001-05-02 TW TW090110515A patent/TWI237059B/zh not_active IP Right Cessation
- 2001-05-04 ID IDP00200100361D patent/ID30106A/id unknown
- 2001-05-04 CZ CZ20011576A patent/CZ20011576A3/cs unknown
- 2001-05-04 AR ARP010102123A patent/AR031844A1/es unknown
- 2001-05-04 CA CA002346426A patent/CA2346426C/en not_active Expired - Fee Related
- 2001-05-07 PL PL01347407A patent/PL347407A1/xx not_active Application Discontinuation
- 2001-05-07 ZA ZA200103666A patent/ZA200103666B/xx unknown
- 2001-05-07 AU AU43758/01A patent/AU782597B2/en not_active Ceased
- 2001-05-07 US US09/850,545 patent/US6828134B2/en not_active Expired - Fee Related
- 2001-05-07 HU HU0101874A patent/HUP0101874A3/hu unknown
- 2001-05-07 RU RU2001112671/13A patent/RU2213778C2/ru not_active IP Right Cessation
- 2001-05-07 KR KR10-2001-0024679A patent/KR100488385B1/ko not_active Expired - Fee Related
- 2001-05-07 MX MXPA01004626A patent/MXPA01004626A/es active IP Right Grant
- 2001-05-07 JP JP2001136141A patent/JP2002000293A/ja active Pending
- 2001-05-08 BR BR0101802-7A patent/BR0101802A/pt not_active IP Right Cessation
- 2001-05-08 SG SG200102673A patent/SG100688A1/en unknown
-
2002
- 2002-03-14 HK HK02101977.3A patent/HK1040264A1/zh unknown
-
2004
- 2004-03-02 US US10/791,462 patent/US7351567B2/en not_active Expired - Fee Related
-
2007
- 2007-06-28 US US11/769,776 patent/US20070249025A1/en not_active Abandoned
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