AR100032A1 - Derivados antibacterianos de 1h-indazol y 1h-indol - Google Patents
Derivados antibacterianos de 1h-indazol y 1h-indolInfo
- Publication number
- AR100032A1 AR100032A1 ARP140104742A ARP140104742A AR100032A1 AR 100032 A1 AR100032 A1 AR 100032A1 AR P140104742 A ARP140104742 A AR P140104742A AR P140104742 A ARP140104742 A AR P140104742A AR 100032 A1 AR100032 A1 AR 100032A1
- Authority
- AR
- Argentina
- Prior art keywords
- hydroxymethyl
- cycloprop
- methyl
- cyclopropyl
- trans
- Prior art date
Links
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
- 230000000844 anti-bacterial effect Effects 0.000 title 1
- -1 trifluoromethoxy, amino Chemical group 0.000 abstract 31
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 abstract 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005133 alkynyloxy group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000004990 dihydroxyalkyl group Chemical group 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 abstract 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 abstract 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000005309 thioalkoxy group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13198338 | 2013-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR100032A1 true AR100032A1 (es) | 2016-09-07 |
Family
ID=49880464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP140104742A AR100032A1 (es) | 2013-12-19 | 2014-12-18 | Derivados antibacterianos de 1h-indazol y 1h-indol |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US9624206B2 (https=) |
| EP (1) | EP3083567B1 (https=) |
| JP (1) | JP6407288B2 (https=) |
| KR (1) | KR20160098503A (https=) |
| CN (1) | CN105829288B (https=) |
| AR (1) | AR100032A1 (https=) |
| AU (1) | AU2014368619B2 (https=) |
| BR (1) | BR112016014115A8 (https=) |
| CA (1) | CA2933604A1 (https=) |
| CL (1) | CL2016001524A1 (https=) |
| EA (1) | EA030730B1 (https=) |
| ES (1) | ES2666130T3 (https=) |
| IL (1) | IL246201A0 (https=) |
| MA (1) | MA39189A1 (https=) |
| MX (1) | MX360983B (https=) |
| PH (1) | PH12016501102A1 (https=) |
| PL (1) | PL3083567T3 (https=) |
| SG (1) | SG11201605014YA (https=) |
| TR (1) | TR201807881T4 (https=) |
| TW (1) | TW201609641A (https=) |
| WO (1) | WO2015091741A1 (https=) |
| ZA (1) | ZA201604968B (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR097617A1 (es) | 2013-09-13 | 2016-04-06 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos del 2h-indazol |
| AR099612A1 (es) | 2014-03-04 | 2016-08-03 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona |
| CA2948077A1 (en) | 2014-05-16 | 2015-11-19 | Actelion Pharmaceuticals Ltd | Antibacterial quinazoline-4(3h)-one derivatives |
| KR20170086079A (ko) | 2014-11-19 | 2017-07-25 | 액테리온 파마슈티칼 리미티드 | 항균성 벤조티아졸 유도체 |
| AR105646A1 (es) | 2015-08-11 | 2017-10-25 | Actelion Pharmaceuticals Ltd | Agentes antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituida |
| CA2991281A1 (en) * | 2015-08-28 | 2017-03-09 | Idorsia Pharmaceuticals Ltd | Antibacterial annulated pyrrolidin-2-one derivatives |
| AR105848A1 (es) * | 2015-08-31 | 2017-11-15 | Actelion Pharmaceuticals Ltd | Derivados heterocíclicos antibacterianos |
| AR105889A1 (es) | 2015-09-03 | 2017-11-22 | Actelion Pharmaceuticals Ltd | Compuestos antibacterianos 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona sustituidos |
| WO2017198647A1 (en) * | 2016-05-17 | 2017-11-23 | Idorsia Pharmaceuticals Ltd | 6-(buta-1,3-diyn-1-yl)benzo[d]thiazole derivatives |
| WO2018216822A1 (en) | 2017-05-25 | 2018-11-29 | Taisho Pharmaceutical Co., Ltd. | Novel imidazole derivatives |
| WO2019086452A1 (en) * | 2017-10-31 | 2019-05-09 | Idorsia Pharmaceuticals Ltd | Antibacterial heteroaromatic compounds |
| CN113666860B (zh) * | 2020-05-14 | 2024-03-15 | 鲁南制药集团股份有限公司 | 一种7-乙基色醇的制备方法 |
| CN119014415B (zh) * | 2024-08-19 | 2025-09-05 | 浙江大学 | 1-甲氧基吲哚在驱避和/或杀灭害虫中的应用 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100984595B1 (ko) | 2002-03-13 | 2010-09-30 | 어레이 바이오파마 인크. | Ｍｅｋ 억제제로서의 ｎ3 알킬화 벤즈이미다졸 유도체 |
| DE102004017930A1 (de) | 2004-04-14 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| EP1809282B1 (en) | 2004-10-18 | 2013-01-09 | Amgen, Inc | Thiadiazole compounds and methods of use |
| WO2006099972A1 (en) | 2005-03-23 | 2006-09-28 | F. Hoffmann-La Roche Ag | Acetylenyl-pyrazolo-pvrimidine derivatives as mglur2 antagonists |
| TWI519508B (zh) | 2007-06-12 | 2016-02-01 | Achaogen Inc | 抗菌劑 |
| EP2432468A2 (en) | 2009-05-20 | 2012-03-28 | Ardea Biosciences, Inc. | Methods of modulating uric acid levels |
| WO2011045703A2 (en) * | 2009-10-13 | 2011-04-21 | Pfizer Inc. | C-linked hydroxamic acid derivatives useful as antibacterial agents |
| WO2011073845A1 (en) | 2009-12-16 | 2011-06-23 | Pfizer Inc. | N-linked hydroxamic acid derivatives useful as antibacterial agents |
| GB2483736B (en) | 2010-09-16 | 2012-08-29 | Aragon Pharmaceuticals Inc | Estrogen receptor modulators and uses thereof |
| MX2013005200A (es) | 2010-11-10 | 2013-06-28 | Achaogen Inc | Derivados de acido hidroxamico y su so en el tratamiento de infecciones bacterianas. |
| CN103328482A (zh) | 2011-01-03 | 2013-09-25 | 韩美药品株式会社 | 用于调节g蛋白-偶联受体的新双环化合物 |
| ES2626457T3 (es) * | 2011-03-07 | 2017-07-25 | Pfizer Inc. | Derivados de fluoro-piridinona útiles como agentes antibacterianos |
| ES2526687T3 (es) | 2011-04-08 | 2015-01-14 | Pfizer Inc. | Derivados de isoxazol útiles como agentes antibacterianos |
| CA2830866A1 (en) * | 2011-04-08 | 2012-10-11 | Pfizer Inc. | Imidazole, pyrazole, and triazole derivatives useful as antibacterial agents |
| EP2847162A1 (en) | 2012-05-09 | 2015-03-18 | Achaogen, Inc. | Antibacterial agents |
| EP2847168A1 (en) | 2012-05-10 | 2015-03-18 | Achaogen, Inc. | Antibacterial agents |
| AR097617A1 (es) | 2013-09-13 | 2016-04-06 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos del 2h-indazol |
| AR099612A1 (es) | 2014-03-04 | 2016-08-03 | Actelion Pharmaceuticals Ltd | Derivados antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona |
| CA2948077A1 (en) | 2014-05-16 | 2015-11-19 | Actelion Pharmaceuticals Ltd | Antibacterial quinazoline-4(3h)-one derivatives |
-
2014
- 2014-12-18 EA EA201600475A patent/EA030730B1/ru not_active IP Right Cessation
- 2014-12-18 US US15/106,790 patent/US9624206B2/en not_active Expired - Fee Related
- 2014-12-18 CA CA2933604A patent/CA2933604A1/en not_active Abandoned
- 2014-12-18 AU AU2014368619A patent/AU2014368619B2/en not_active Ceased
- 2014-12-18 SG SG11201605014YA patent/SG11201605014YA/en unknown
- 2014-12-18 WO PCT/EP2014/078384 patent/WO2015091741A1/en not_active Ceased
- 2014-12-18 TW TW103144395A patent/TW201609641A/zh unknown
- 2014-12-18 BR BR112016014115A patent/BR112016014115A8/pt not_active Application Discontinuation
- 2014-12-18 PL PL14812752T patent/PL3083567T3/pl unknown
- 2014-12-18 KR KR1020167019669A patent/KR20160098503A/ko not_active Ceased
- 2014-12-18 ES ES14812752.5T patent/ES2666130T3/es active Active
- 2014-12-18 CN CN201480067976.9A patent/CN105829288B/zh not_active Expired - Fee Related
- 2014-12-18 MA MA39189A patent/MA39189A1/fr unknown
- 2014-12-18 TR TR2018/07881T patent/TR201807881T4/tr unknown
- 2014-12-18 EP EP14812752.5A patent/EP3083567B1/en not_active Not-in-force
- 2014-12-18 AR ARP140104742A patent/AR100032A1/es unknown
- 2014-12-18 JP JP2016541300A patent/JP6407288B2/ja not_active Expired - Fee Related
- 2014-12-18 MX MX2016007991A patent/MX360983B/es active IP Right Grant
-
2016
- 2016-06-09 PH PH12016501102A patent/PH12016501102A1/en unknown
- 2016-06-14 IL IL246201A patent/IL246201A0/en unknown
- 2016-06-16 CL CL2016001524A patent/CL2016001524A1/es unknown
- 2016-07-18 ZA ZA2016/04968A patent/ZA201604968B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2666130T3 (es) | 2018-05-03 |
| MX360983B (es) | 2018-11-22 |
| TW201609641A (zh) | 2016-03-16 |
| TR201807881T4 (tr) | 2018-06-21 |
| JP6407288B2 (ja) | 2018-10-17 |
| US20170029411A1 (en) | 2017-02-02 |
| CL2016001524A1 (es) | 2017-01-27 |
| BR112016014115A2 (https=) | 2017-08-08 |
| SG11201605014YA (en) | 2016-07-28 |
| ZA201604968B (en) | 2018-11-28 |
| CN105829288A (zh) | 2016-08-03 |
| CA2933604A1 (en) | 2015-06-25 |
| PH12016501102A1 (en) | 2016-07-11 |
| EA030730B1 (ru) | 2018-09-28 |
| US9624206B2 (en) | 2017-04-18 |
| PL3083567T3 (pl) | 2018-08-31 |
| AU2014368619B2 (en) | 2018-11-22 |
| WO2015091741A1 (en) | 2015-06-25 |
| CN105829288B (zh) | 2019-01-15 |
| EP3083567B1 (en) | 2018-03-07 |
| JP2017500336A (ja) | 2017-01-05 |
| AU2014368619A1 (en) | 2016-07-28 |
| MX2016007991A (es) | 2016-10-07 |
| IL246201A0 (en) | 2016-08-02 |
| EP3083567A1 (en) | 2016-10-26 |
| MA39189A1 (fr) | 2017-06-30 |
| BR112016014115A8 (pt) | 2017-12-26 |
| EA201600475A1 (ru) | 2016-11-30 |
| KR20160098503A (ko) | 2016-08-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AR100032A1 (es) | Derivados antibacterianos de 1h-indazol y 1h-indol | |
| AR097617A1 (es) | Derivados antibacterianos del 2h-indazol | |
| AR099612A1 (es) | Derivados antibacterianos de 1,2-dihidro-3h-pirrolo[1,2-c]imidazol-3-ona | |
| AR100428A1 (es) | Derivados antibacterianos quinazolina-4(3h)-ona | |
| AR100033A1 (es) | Compuestos y composiciones para inhibir la actividad de shp2 | |
| AR094667A1 (es) | Piridonamidas como moduladores de canales de sodio | |
| AR100137A1 (es) | Compuestos 4-amino-imidazoquinolina | |
| WO2015042297A8 (en) | Compounds for treating prostate cancer | |
| AR094309A1 (es) | Compuesto heterociclico fusionado y uso del mismo para el control de plagas | |
| AR118706A2 (es) | Compuesto para el control de plagas y vegetación no deseada, procedimiento para prepararlo, composición que lo comprende, y compuesto intermediario relacionado | |
| EA201591486A1 (ru) | Соединения имидазопиридина | |
| AR082138A1 (es) | 1-hidroxiimino-3-fenil-propanos | |
| AR094537A1 (es) | COMPUESTOS DE PIRIDILO SUSTITUIDOS CON ALQUILAMIDA ÚTILES COMO MODULADORES DE LAS RESPUESTAS DE IL-12, IL-23 Y/O IFNa | |
| AR074021A1 (es) | Compuestos heterociclicos fusionados como moduladores del canal ionico | |
| ES2531315T3 (es) | Compuestos de fosfinato antivíricos | |
| AR101815A1 (es) | Compuestos y composiciones como inhibidores de quinasa | |
| AR091519A1 (es) | Inhibidores pirrolopirazona de tanquirasa | |
| MY161134A (en) | Piperazine compound having a pgds inhibitory effect | |
| EA201690879A1 (ru) | Новое триазолопиридиновое соединение | |
| AR098871A1 (es) | Métodos de proceso para inhibidores de fosfatidilinositol 3-quinasa | |
| AR102687A1 (es) | Derivados de benzotiazol antibacterianos | |
| AR091773A1 (es) | Inhibidores de la histona desacetilasa y composiciones y sus metodos de uso | |
| CY1120680T1 (el) | Ανταγωνιστες η3 που περιεχουν συνταξη πυρηνα φαινοξυπιπεριδινης | |
| AR098818A1 (es) | Derivados de oxindol, preparación de los mismos y uso terapéutico de los mismos | |
| AR097253A1 (es) | Derivado de pirazolilpirazol sustituido y el uso del mismo como herbicida |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |