Efficient synthesis of 5-(hydroxymethyl)piperazin-2-ones using automatically prepared chiral bromocarboxylic acid and Garner's aldehyde as versatile building blocks.

An efficient method for the synthesis of substituted 5-(hydroxymethyl)piperazin-2-ones was established by using an automated synthesis process. Thirteen piperazinones were synthesized from chiral α-bromocarboxylic acids and Garner's aldehyde which were prepared by using our originally developed automated synthesizer, ChemKonzert®. The automated method of synthesizing chiral α-bromocarboxylic acids was efficient and safe because the rate of the dropwise addition of the reagent can be controlled using the automated synthesizer. This method is expected to contribute to the synthesis of pharmaceuticals.

A case of symptomatic tumoral calcinosis on the great toe and review of the literature.

A 67-year-old woman with no specific medical history showed a hard mass on her great toe for several years. The lesion was elastic, round, and had good mobility. An X-ray showed the lesion to be a calcified "chicken wire" lesion; CT and MRI findings indicated it as a benign subcutaneous calcified tumor. Therefore, a resection biopsy was performed. The mass was a 20 x 20 mm calcified tumor diagnosed as tumoral calcinosis. Pathological findings showed that the calcified lesion lay in fibrous connective tissue and characteristic cells were seen around the calcification site. In this case, the lesion was mature and surgical resection was successful. The patient showed no symptoms or recurrence 3 years after the surgery.

Reconstruction of lateral ligament with arthroscopic drilling for treatment of early-stage osteoarthritis in unstable ankles.

PURPOSE: The purpose of this study was to investigate the clinical, radiologic, and arthroscopic results of lateral stabilization with reconstruction of the lateral ligaments and cartilage regeneration with arthroscopic drilling for the treatment of moderate osteoarthritis of the ankle with simultaneous lateral instability of the ankle (LIA). METHODS: There were 16 cases with LIA, 7 of which had stage 2 osteoarthritis of the ankle according to the radiographic classification of Takakura et al. and 9 of which had stage 3 osteoarthritis. Arthroscopic drilling was performed with a motorized drill for the chondral defect, and anatomic reconstruction of the lateral ligament with an autologous gracilis tendon graft was performed for LIA. Clinical, radiologic, and arthroscopic evaluations were performed before surgery and at the most recent follow-up. RESULTS: In stage 2 cases the mean score on the American Orthopaedic Foot and Ankle Society ankle-hindfoot scale was 42.5 +/- 6.8 points before surgery and 87.4 +/- 4.2 points at the most recent follow-up (P = .0002). In stage 3 cases the mean score was 41.4 +/- 8.0 points before surgery and 61.2 +/- 7.4 points at the most recent follow-up (P = .0001). The talar tilt angles on standard stress radiography in stage 2 cases were 17.4 degrees +/- 4.5 degrees before surgery and 3.4 degrees +/- 0.9 degrees at the most recent follow-up (P = .0009). In stage 3 cases the mean talar tilt angles were 18.2 degrees +/- 4.7 degrees before surgery and 3.6 degrees +/- 0.7 degrees at the most recent follow-up (P < .0001). In all cases the radiographic classification of Takakura et al. was unchanged between assessments before surgery and at the most recent follow-up. With regard to arthroscopic findings at 1 year after surgery, the International Cartilage Repair Society's cartilage repair assessment score showed 6 nearly normal and 1 abnormal stage 2 cases and 1 abnormal and 8 severely abnormal stage 3 cases. CONCLUSIONS: Reconstruction of the lateral ligament with arthroscopic drilling as a surgical procedure for the treatment of stage 2 osteoarthritis with LIA can be recommended. LEVEL OF EVIDENCE: Level IV, therapeutic case series.

Retrograde drilling for osteochondral lesions of the talar dome.

BACKGROUND: For the treatment of osteochondral lesions of the talar dome without detachment of the cartilage, there is little information on whether transmalleolar drilling or retrograde drilling is more effective in terms of clinical and morphologic evaluations. HYPOTHESIS: Retrograde drilling may be more effective than transmalleolar drilling for lesions without cartilage detachment. STUDY DESIGN: Case control study; Level of evidence, 3. METHODS: Subjects were 30 patients with lesions on 1 foot of grade 0 or I, determined according to a modified Pritsch classification system. Nineteen patients underwent transmalleolar drilling (TMD group), and 11 patients underwent retrograde drilling (RD group). Ankle arthroscopy was performed 1 year postoperatively to evaluate cartilage conditions. RESULTS: Arthroscopic findings revealed that in the TMD group, 11 lesions (57.9%) were unchanged (grade I), and 8 lesions (42.1%) had deteriorated from grade 0 to I; in the RD group, 3 lesions (27.2%) had improved from grade I to 0, and 8 (72.8%) were unchanged (2 grade 0 lesions and 6 grade I lesions). There was a significant difference between the 2 groups in the distribution of cases that had improved, were unchanged, or had deteriorated (P < .0001). CONCLUSIONS: This study showed that compared with transmalleolar drilling, retrograde drilling for osteochondral lesions of the talar dome can improve the arthroscopic assessment of the lesions.

Arthroscopic assessment for intra-articular disorders in residual ankle disability after sprain.

BACKGROUND: After ankle sprain, there can be many causes of disability, the origins of which cannot be determined using standard diagnostic tools. HYPOTHESIS: Ankle arthroscopy is a useful tool in identifying intra-articular disorders of the talocrural joint in cases of residual ankle disability after sprain. STUDY DESIGN: Cohort study (diagnosis); Level of evidence, 2. METHODS: The authors gathered the independent diagnostic results of physical examination, standard mortise and lateral radiography, stress radiography of the talocrural joint, and magnetic resonance imaging for 72 patients with residual ankle disability lasting more than 2 months after injury (mean, 7 months after injury). They performed arthroscopic procedures and compared the double-blind results. RESULTS: In all cases, the arthroscopic results matched those of other means of diagnosis. In 14 cases, the arthroscopic approach exceeded the capabilities of the other methods. Including duplications, 39 patients (54.2%) had anterior talofibular ligament injuries, 17 patients (23.6%) had distal tibiofibular ligament injuries, 29 patients (40.3%) had osteochondral lesions, 13 patients (18%) had symptomatic os subfibulare, 3 patients (4.2%) had anterior impingement exostosis, and 3 patients (4.2%) had impingement due to abnormally fibrous bands. There were only 2 cases in which the cause of symptoms could not be detected by ankle arthroscopy, compared with 16 cases in which the cause of disability could not be detected using standard methods. In 3 cases (17.6%) of distal tibiofibular ligament injuries, 8 cases (27.6%) of osteochondral lesions, and all 3 cases (100%) of impingement of an abnormal fibrous band, ankle arthroscopy was the only method capable of diagnosing the cause of residual ankle pain after a sprain. CONCLUSION: The present results suggest that arthroscopy can be used to diagnose the cause of residual pain after an ankle sprain in most cases that are otherwise undiagnosable by clinical examination and imaging study.

Diagnosis and treatment of combined intra-articular disorders in acute distal fibular fractures.

BACKGROUND: Some patients have residual ankle pain and disability after the treatment of an ankle fracture, despite the fracture site being well aligned. We identified intra-articular disorders in distal fibular fractures and sought to clarify the results of their operative treatment. METHODS: This is a prospective, randomized study. Seventy-two patients with Weber type B distal fibular fractures were randomly treated with arthroscopy-assisted open reduction and internal fixation (AORIF) or with open reduction and internal fixation without arthroscopy (ORIF). In the AORIF group, the patients were followed for a mean duration of 3 years 4 months (range, 2 years 4 months-4 years 5 months). There were 27 male patients and 14 female patients. The mean age of the patients at the time of surgery was 36 years (range, 20-64 years). In the ORIF group, the patients were followed for a mean duration of 3 years 5 months (range, 2 years 7 months-4 years 5 months). There were 21 male patients and 10 female patients. The mean age of the patients at the time of surgery was 38 years (range, 20-58 years). We described intra-articular disorders in the AORIF group using ankle arthroscopy and compared their operative results with those of the ORIF group. RESULTS: Including duplication, the arthroscopic findings showed 30 cases with osteochondral lesions of the talar dome (73.2%) and 33 cases with tibiofibular syndesmosis disruptions (80.5%). Six cases (14.6%) had no combined disorders. The mean AOFAS score was 91.0 +/- 3.5 (range, 85-100) in the AORIF group, in contrast to 87.6 +/- 5.5 (range, 77-97) in the ORIF group (p = 0.0106). CONCLUSION: In the treatment of distal fibular fractures, precisely diagnosing and treating the combined intra-articular disorders is important for gaining satisfactory clinical results.

Arthroscopic treatment for anterior impingement exostosis of the ankle: application of three-dimensional computed tomography.

The purpose of this study was to evaluate the operative results of excision of anterior impingement exostoses of the ankle. Preoperative three-dimensional computed tomography (3DCT) was used to make the diagnoses. The authors evaluated 16 ankles of 16 patients who underwent arthroscopic resection of the osteophytes of their anterior distal tibia or dorsal talus. They were followed up for 24-51 months. All 16 patients had 3DCT preoperatively, which allowed the authors to determine the exact location, shape, size, and number of the osteophytes. All of the osteophytes were resected using arthroscopic techniques. At the time of the most recent follow-up, the mean AOFAS score was 80.5 +/- 4.9 points at preoperation, and 97.0 +/- 3.7 points at the most recent follow-up. There were significant differences between the pre- and postoperative AOFAS scores and those of the most recent follow-up period for each group (p <.0001). It is necessary to clarify the location, size, shape, and number of all of the osteophytes preoperatively using 3DCT, and to then resect them all.

Osteochondral lesions of the talar dome associated with trauma.

PURPOSE: The purpose of this study was to clarify the differences in the causes of osteochondral lesions (OCL) of the ankle based on the presence of distal fibular fractures and lateral instability of the ankle. TYPE OF STUDY: Case series. METHODS: We evaluated 92 cases of distal fibular fractures and 86 cases of lateral instability of the ankle, including 36 feet with subacute lateral instability of the ankle and 50 feet with chronic lateral instability of the ankle. In diagnosing OCL, we used a combination of magnetic resonance imaging to evaluate the subchondral conditions and ankle arthroscopy to evaluate the chondral conditions. RESULTS: Of a total of 92 distal fibular fractures, 65 cases (70.7%) had OCL at the time of osteosynthesis and 27 did not (29.3%). Among the latter group, 2 developed OCL about 1 year after surgery. Of a total of 86 cases of lateral instability of the ankle, 35 (40.7%) had OCL. Among the subacute cases, 7 of 36 (19.4%) had OCL, versus 28 of 50 cases (56.0%) with chronic lateral instability of the ankle. CONCLUSIONS: Our study suggests that recurrent ankle sprains with remaining lateral instability and distal fibular fractures could be one of the causes of OCL of the ankle.

Arthroscopic drilling for chondral, subchondral, and combined chondral-subchondral lesions of the talar dome.

PURPOSE: We investigated the efficacy of drilling as a treatment for chondral (C), subchondral (S), and combined chondral-subchondral (CS) lesions of the talar dome associated with trauma, using magnetic resonance imaging (MRI), ankle arthroscopy, and the ankle-hindfoot scale of the American Orthopaedic Foot and Ankle Society (AOFAS score). TYPE OF STUDY: Case series study. METHODS: Arthroscopic drilling was performed on 72 patients whose lesions were less than 7 mm in diameter. The patients included 45 men and boys and 27 women and girls whose age at the time of surgery was between 14 and 57 years (mean age, 30.7 +/- 9.5 years). They were followed up for 24 to 71 months (mean follow-up, 39 +/- 6.4 months). RESULTS: There were 13 cases of chondral lesions, 10 cases of S lesions, and 49 cases of CS lesions. The MRI findings revealed that in the chondral lesion group, 13 cases were unchanged and 0 deteriorated; in the S lesion group, 2 improved, 8 were unchanged, and 0 deteriorated; and in the CS lesion group, 13 improved, 36 were unchanged, and 0 deteriorated. The arthroscopic findings showed that in the chondral lesion group, 2 improved, 9 were unchanged, and 1 deteriorated; in the S lesion group, all 8 cases deteriorated; and in the CS lesion group, 28 improved, 22 were unchanged, and 0 deteriorated. Drilling did not always improve the MRI and arthroscopic findings of the 3 respective types of lesions. However, the mean AOFAS score at the most recent follow-up was excellent; 91.7 +/- 2.4 points in the chondral lesion group, 93.1 +/- 2.1 points in the S lesion group, and 98.8 +/- 1.2 points in the CS lesion group. CONCLUSIONS: Our study shows that drilling did not always improve the MRI and arthroscopic findings. However, the clinical results obtained as measured by the AOFAS score were excellent.

Injury of the tibiofibular syndesmosis: value of MR imaging for diagnosis.

PURPOSE: To compare the use of magnetic resonance (MR) imaging with the use of arthroscopy for the diagnosis of tibiofibular syndesmotic injury. MATERIALS AND METHODS: This study involved 58 patients who had ankle sprains or distal fibular fractures and underwent surgery. All patients were examined with MR imaging for diagnosis of tibiofibular syndesmotic injury. When MR imaging revealed ligament discontinuity (criterion 1) or either a wavy or curved ligament contour or nonvisualization of the ligament (criterion 2), the injury was considered to be a ligament disruption. After MR imaging, ankle arthroscopy was performed in all patients for a definitive diagnosis of ligament disruption. RESULTS: Arthroscopic findings showed anteroinferior tibiofibular ligament (AITFL) disruption in 28 patients and posteroinferior tibiofibular ligament (PITFL) disruption in five patients. When an MR imaging diagnosis was based on criterion 1 only, the diagnosis of AITFL disruption was made with a sensitivity of 100%, a specificity of 70%, and an accuracy of 84%, and the diagnosis of PITFL disruption was made with a sensitivity of 100%, a specificity of 94%, and an accuracy of 95%. When an MR imaging diagnosis was based on criteria 1 and 2, the diagnosis of AITFL disruption was made with a sensitivity of 100%, a specificity of 93%, and an accuracy of 97%, whereas the diagnosis of PITFL disruption was made with a sensitivity of 100%, a specificity of 100%, and an accuracy of 100%. CONCLUSION: MR imaging with use of both criteria is highly accurate for the diagnosis of tibiofibular syndesmotic disruption.

Symptomatic os subfibulare caused by accessory ossification: a case report.

Separated ossicles at the tip of the lateral malleolus, the condition known as os subfibulare, are sometimes a cause of ankle pain. There are two theories regarding the origin of os subfibulare. One theory proposes that it is caused by an avulsion fracture attributable to pull of the anterior talofibular ligament, whereas the other theory proposes that it is the result of an accessory ossification center. However, some authors have reported that os subfibulare is an avulsion fracture and few reports of accessory ossification have been described recently. A patient with os subfibulare that may have been caused by accessory ossification rather than an avulsion fracture was treated by the current authors.