BR9811679A - Antifúngicos de 1,3-dioxolanos 2,4,4-trissubstituìdos. - Google Patents
Antifúngicos de 1,3-dioxolanos 2,4,4-trissubstituìdos.Info
- Publication number
- BR9811679A BR9811679A BR9811679-7A BR9811679A BR9811679A BR 9811679 A BR9811679 A BR 9811679A BR 9811679 A BR9811679 A BR 9811679A BR 9811679 A BR9811679 A BR 9811679A
- Authority
- BR
- Brazil
- Prior art keywords
- aryl
- alkyl
- antifungals
- hydrogen
- independently
- Prior art date
Links
- 229940121375 antifungal agent Drugs 0.000 title abstract 3
- 125000006091 1,3-dioxolane group Chemical class 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract 1
- 125000000815 N-oxide group Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- -1 nitro, cyano, amino, hydroxy Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Patente de Invenção: <B>"ANTIFúNGICOS DE 1,3-DIOXOLANOS 2,4,4-TRISSUBSTITUìDOS"<D>. A invenção refere-se a novos compostos de fórmula (I), a uma forma N-óxido, a um sal de adição de ácido farmaceuticamente aceitável ou a uma forma estereoquimicamente isomérica dos compostos, nos quais n é zero, 1, 2 ou 3; X é N ou CH; cada R¹ independentemente é halo, nitro, ciano, amino, hidroxi, C~ 1-4~ alquila, C~ 1-4~ alquiloxi ou trifluormetila; R² é hidrogênio; C~ 3-7~ alquenila; C~ 3-7~ alquinila, arila; C~ 3-7~ cicloalquila; opcionalmente C~ 1-6~ alquila substituída; R³ e R^ 4^ cada um independentemente são hidrogênio, C~ 1-6~ alquila, C~ 3-7~ cicloalquila ou arila; ou R³ e R^ 4^ tomados juntamente formam um radical bivalente -R³ -R^ 4^- de fórmula (a), (b), (c), (d) ou (e), onde R^ 5a^, R^ 5b^, R^ 5c^ e R^ 5d^, cada um independentemente, são hidrogênio, C~ 1-6~ alquila ou arila; e arila é fenila opcionalmente substituída; como antifúngicos; sua preparação, composições que contêm os compostos e seu uso como medicamento.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97202181 | 1997-07-11 | ||
| PCT/EP1998/004194 WO1999002523A1 (en) | 1997-07-11 | 1998-07-07 | 2,4,4-trisubstituted-1,3-dioxolane antifungals |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| BR9811679A true BR9811679A (pt) | 2000-09-19 |
| BRPI9811679B1 BRPI9811679B1 (pt) | 2016-10-18 |
| BRPI9811679B8 BRPI9811679B8 (pt) | 2021-05-25 |
Family
ID=8228553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI9811679A BRPI9811679B8 (pt) | 1997-07-11 | 1998-07-07 | antifúngicos de 1-{4-[4-(4-{[4-fenil-4-(1 h-1,2,4-triazol-1-ilmetil)-1,3-dioxolan-2-il]metóxi}fenil)piperazin-1-il]fenil}imidazolidin-2-onas substituídas |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US6387906B1 (pt) |
| EP (1) | EP1068200B1 (pt) |
| KR (1) | KR100540460B1 (pt) |
| AP (1) | AP1379A (pt) |
| AR (1) | AR015130A1 (pt) |
| AT (1) | ATE289303T1 (pt) |
| AU (1) | AU749760B2 (pt) |
| BG (1) | BG64314B1 (pt) |
| BR (1) | BRPI9811679B8 (pt) |
| CA (1) | CA2295090C (pt) |
| CZ (1) | CZ297453B6 (pt) |
| DE (1) | DE69829082T2 (pt) |
| DK (1) | DK1068200T3 (pt) |
| EA (1) | EA002828B1 (pt) |
| EE (1) | EE04155B1 (pt) |
| ES (1) | ES2238765T3 (pt) |
| GE (1) | GEP20033054B (pt) |
| HR (1) | HRP20000007B1 (pt) |
| HU (1) | HU225159B1 (pt) |
| ID (1) | ID23783A (pt) |
| IL (1) | IL133919A (pt) |
| MY (1) | MY118844A (pt) |
| NO (1) | NO318328B1 (pt) |
| NZ (1) | NZ501982A (pt) |
| PL (1) | PL193703B1 (pt) |
| PT (1) | PT1068200E (pt) |
| SI (1) | SI1068200T1 (pt) |
| SK (1) | SK285321B6 (pt) |
| TR (1) | TR200000154T2 (pt) |
| TW (1) | TW593312B (pt) |
| UA (1) | UA71543C2 (pt) |
| WO (1) | WO1999002523A1 (pt) |
| ZA (1) | ZA986160B (pt) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19945982A1 (de) * | 1999-09-24 | 2001-03-29 | Knoll Ag | Geschwindigkeitsbestimmte Partikel |
| US20040086567A1 (en) * | 2002-10-30 | 2004-05-06 | Pawan Seth | Bioequivalent composition of itraconazole and a hydrophilic polymer |
| CN102015582A (zh) * | 2008-03-03 | 2011-04-13 | 施泰福实验室股份有限公司 | 光学纯二元醇和二氧戊环化合物的制备方法 |
| US8431699B2 (en) * | 2009-02-27 | 2013-04-30 | Vertichem Corporation | Method for manufacture of 2-oxoimidazolidines |
| CN105777486B (zh) * | 2016-03-30 | 2018-09-11 | 浙江大学宁波理工学院 | 一种2-[2-(2，4-二氟苯基)-2-丙烯-1-基]-1，3-丙二醇的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4218458A (en) * | 1978-06-23 | 1980-08-19 | Janssen Pharmaceutica, N.V. | Heterocyclic derivatives of (4-aryloxy-methyl-1,3-dioxolan-2-yl)methyl-1H-imidazoles and 1H-1,2,4-triazoles |
| US4619931A (en) * | 1983-02-28 | 1986-10-28 | Janssen Pharmaceutica, N.V. | [[4-[4-(4-phenyl-1-piperazinyl)phenoxymethyl]-1,3-dioxolan-2-yl]methyl]-1H-imidazoles and 1H-1,2,4-triazoles |
| CA1292472C (en) * | 1985-12-03 | 1991-11-26 | Alfonsus Guilielmus Knaeps | Derivatives of ¬¬4-¬4-(4-phenyl-1-piperazinyl)- phenoxymethyl|-1,3-dioxolan-2-yl|methyl|-1h-imidazoles and 1h-1,2,4-triazoles |
| US4788190A (en) * | 1986-12-24 | 1988-11-29 | Schering Corporation | 2,4,4-tri- and 2,2,4,4-tetra substituted-1,3-dioxolane antifungal, antiallergy compounds |
| NZ233502A (en) * | 1989-06-09 | 1991-11-26 | Janssen Pharmaceutica Nv | 4-(1,2,4-triazole- or imidazole-phenyl-substituted) -1-(1,3-dioxolan-4-ylmethoxyphenyl) piperazine derivatives; preparatory processes: fungicidal and antiviral compositions |
| IL103558A0 (en) | 1991-10-30 | 1993-03-15 | Schering Corp | Tri-substituted tetrahydrofuran antifungals |
| DK0741737T3 (da) * | 1994-01-24 | 2000-05-22 | Janssen Pharmaceutica Nv | Vandopløslige antifugale azoler |
-
1998
- 1998-07-06 TW TW087110868A patent/TW593312B/zh not_active IP Right Cessation
- 1998-07-07 HR HR20000007A patent/HRP20000007B1/xx not_active IP Right Cessation
- 1998-07-07 US US09/462,588 patent/US6387906B1/en not_active Expired - Lifetime
- 1998-07-07 MY MYPI98003075A patent/MY118844A/en unknown
- 1998-07-07 ES ES98940160T patent/ES2238765T3/es not_active Expired - Lifetime
- 1998-07-07 CA CA002295090A patent/CA2295090C/en not_active Expired - Lifetime
- 1998-07-07 DE DE69829082T patent/DE69829082T2/de not_active Expired - Lifetime
- 1998-07-07 HU HU0004459A patent/HU225159B1/hu unknown
- 1998-07-07 UA UA2000010162A patent/UA71543C2/uk unknown
- 1998-07-07 CZ CZ0463799A patent/CZ297453B6/cs not_active IP Right Cessation
- 1998-07-07 TR TR2000/00154T patent/TR200000154T2/xx unknown
- 1998-07-07 GE GEAP19985200A patent/GEP20033054B/en unknown
- 1998-07-07 EP EP98940160A patent/EP1068200B1/en not_active Expired - Lifetime
- 1998-07-07 AP APAP/P/2000/001730A patent/AP1379A/en active
- 1998-07-07 DK DK98940160T patent/DK1068200T3/da active
- 1998-07-07 AT AT98940160T patent/ATE289303T1/de active
- 1998-07-07 WO PCT/EP1998/004194 patent/WO1999002523A1/en not_active Ceased
- 1998-07-07 AU AU88576/98A patent/AU749760B2/en not_active Expired
- 1998-07-07 IL IL13391998A patent/IL133919A/en not_active IP Right Cessation
- 1998-07-07 PT PT98940160T patent/PT1068200E/pt unknown
- 1998-07-07 PL PL98338009A patent/PL193703B1/pl unknown
- 1998-07-07 ID IDW20000032A patent/ID23783A/id unknown
- 1998-07-07 KR KR1019997012503A patent/KR100540460B1/ko not_active Expired - Lifetime
- 1998-07-07 SI SI9830764T patent/SI1068200T1/xx unknown
- 1998-07-07 SK SK1841-99A patent/SK285321B6/sk not_active IP Right Cessation
- 1998-07-07 NZ NZ501982A patent/NZ501982A/xx not_active IP Right Cessation
- 1998-07-07 EA EA200000116A patent/EA002828B1/ru not_active IP Right Cessation
- 1998-07-07 EE EEP200000020A patent/EE04155B1/xx unknown
- 1998-07-07 BR BRPI9811679A patent/BRPI9811679B8/pt not_active IP Right Cessation
- 1998-07-10 ZA ZA9806160A patent/ZA986160B/xx unknown
- 1998-07-10 AR ARP980103376A patent/AR015130A1/es active IP Right Grant
-
1999
- 1999-12-10 BG BG103982A patent/BG64314B1/bg unknown
-
2000
- 2000-01-10 NO NO20000114A patent/NO318328B1/no not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BR9916827A (pt) | Derivados de quinolina 1,2-anelados | |
| BR9804504A (pt) | Isoquinolina-3-carboxamidas substituìdas, sua preparação e seu uso como substâncias farmacêuticas | |
| BR9916282A (pt) | Composto, uso de um um composto e método de tratamento | |
| TR199902606T2 (xx) | Farnesil transferaz� engelleyici kinazolinonlar. | |
| BR9806752A (pt) | Ftalazinonas. | |
| DK1140918T3 (da) | Thrombininhibitorer | |
| BR9913592A (pt) | Compostos, processo de preparação dos compostos, e, composições farmacêuticas | |
| BR0307409A (pt) | Compostos de hidrazida de ácido 2-furanocarboxìlico, composições farmacêuticas contendo os mesmos e uso dos mesmos para preparação de um agente preventivo ou terapêutico | |
| BR0010476A (pt) | Compostos derivados do 4,5,6,7-tetrahidroindazol e seu uso como agentes antitumorais | |
| FI862210A0 (fi) | Imidazoheterocykliska foereningar och foerfarande foer deras framstaellning. | |
| BR9915401A (pt) | Derivados de pirimidinilbenzimidazol e triazinilbenzimidazol e fungicida agrìcola/hortìcola | |
| BR9909197A (pt) | Derivados 1,3,5-triazina tri-substituìdos para o tratamento de infecções por hiv | |
| BR9810021A (pt) | Derivados 9-oxima-eritromicina | |
| CY1106522T1 (el) | Ετepοκυκλικη ενωση και αντικαρκινικο μεσο που πepιεχει την ιδια ως δραστικο συστατικο | |
| BR9808843A (pt) | Derivados de quinolinona 1,8-anelados inibidores da farnesil transferase substituìdos com imidazóis ligados em n ou em c | |
| BR9807339A (pt) | Derivados 3-piperidil-4-oxoquinazolina e composições farmacêuticas compreendendo os mesmos. | |
| BR9813124A (pt) | Compostos indol 2,3-substituìdos como inibidores cox-2 | |
| BR9811769A (pt) | Tetraidro gama-carbolinas | |
| BR9910448A (pt) | Azóis solúveis em água como antifúngicos de amplo aspectro | |
| BR9814376A (pt) | Composto ou um pró-medicamento correspondente, ou um sal farmaceuticamente aceitável ou solvato de um tal composto ou um pró-medicamento deste, uso destes, composição farmacêutica, processo para o tratamento de um paciente humano ou animal não humano sofrendo de, ou sujeito a, condições que podem ser melhoradas pela admnistração de um inibidor da adesão celular mediada por &4ß1, e, resina | |
| BR9811679A (pt) | Antifúngicos de 1,3-dioxolanos 2,4,4-trissubstituìdos. | |
| BR0002505A (pt) | Derivados de 4-arilpiperidina para o tratamento de prurido | |
| BR9810314A (pt) | Derivados de 5-substituìdo-1,2,4-tiadiazolila que inibem de angiogênese | |
| BR9908861A (pt) | Ciclooctadepsipeptìdeos e seu uso para o combate de endoparasitas | |
| BR9809643A (pt) | Compostos heterocìclicos, seu processo de preparo e as composições farmacêuticas que os contêm |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B07A | Application suspended after technical examination (opinion) [chapter 7.1 patent gazette] | ||
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B09B | Patent application refused [chapter 9.2 patent gazette] |
Free format text: INDEFERIMENTO DO PRESENRTE PEDIDO PERMANECE O OBICE AO PATENTEAMENTO POIS A MATERIA PLEITEADA CONTINUA EM DESACORDO COM OS ARTIGOS 8O E 13 DA LPI |
|
| B12B | Appeal against refusal [chapter 12.2 patent gazette] | ||
| B07E | Notification of approval relating to section 229 industrial property law [chapter 7.5 patent gazette] |
Free format text: NOTIFICACAO DE ANUENCIA RELACIONADA COM O ART 229 DA LPI |
|
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |
Free format text: PRAZO DE VALIDADE: 10 (DEZ) ANOS CONTADOS A PARTIR DE 18/10/2016, OBSERVADAS AS CONDICOES LEGAIS. |
|
| B16C | Correction of notification of the grant [chapter 16.3 patent gazette] |
Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 07/07/1998 OBSERVADAS AS CONDICOES LEGAIS. PATENTE CONCEDIDA CONFORME ADI 5.529/DF |
|
| B21A | Patent or certificate of addition expired [chapter 21.1 patent gazette] |
Free format text: PATENTE EXTINTA EM 07/07/2018 |